WO1997018705A2 - Dry formulations of pesticides for controlling ectoparasites on animals - Google Patents

Dry formulations of pesticides for controlling ectoparasites on animals Download PDF

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Publication number
WO1997018705A2
WO1997018705A2 PCT/US1996/018231 US9618231W WO9718705A2 WO 1997018705 A2 WO1997018705 A2 WO 1997018705A2 US 9618231 W US9618231 W US 9618231W WO 9718705 A2 WO9718705 A2 WO 9718705A2
Authority
WO
WIPO (PCT)
Prior art keywords
animal
insecticide
dry formulation
animals
microencapsulated
Prior art date
Application number
PCT/US1996/018231
Other languages
English (en)
French (fr)
Other versions
WO1997018705A3 (en
Inventor
Jeffery Alan Meyer
Robert G. Pennington
Herbert Benson Scher
Original Assignee
Schering-Plough Animal Health Corporation
Zeneca Limited
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 to AU77317/96A priority Critical patent/AU706884B2/en
Application filed by Schering-Plough Animal Health Corporation, Zeneca Limited filed Critical Schering-Plough Animal Health Corporation
Priority to SK647-98A priority patent/SK64798A3/sk
Priority to HU9902703A priority patent/HUP9902703A2/hu
Priority to CA 2237334 priority patent/CA2237334A1/en
Priority to KR1019980703602A priority patent/KR19990067579A/ko
Priority to BR9611722-2A priority patent/BR9611722A/pt
Priority to JP9519791A priority patent/JP2000500494A/ja
Priority to PL96328958A priority patent/PL328958A1/xx
Priority to EP96940432A priority patent/EP0862365A2/en
Priority to IL12444896A priority patent/IL124448A0/xx
Publication of WO1997018705A2 publication Critical patent/WO1997018705A2/en
Publication of WO1997018705A3 publication Critical patent/WO1997018705A3/en
Priority to NO982235A priority patent/NO982235L/no

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
    • A01N25/26—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 in coated particulate form
    • A01N25/28—Microcapsules or nanocapsules
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals

Definitions

  • This invention relates to a method for protecting an animal from infestation by fleas and other ectoparasites. Dry formulations of organophosphate insecticides control fleas on animals when applied to a small, limited area of the animal's coat m a high concentration, low volume, single application. These formulations have unexpected properties which makes their use advantageous in comparison to liquid insecticide formulations which are presently used for the control of fleas on animals.
  • dipping solutions can be upsetting to domestic animals, particularly to cats, who often have a natural aversion to water. Dip solutions are expensive, particularly when only one or a few animals are treated, and the solutions must be properly disposed of following their use to avoid contaminating the environment. Most importantly, all of these applications of pesticide compositions must be repeated frequently, since they are only effective for periods of one to two weeks.
  • cats tend to groom themselves by licking their bodies and fur, they are particularly susceptible to adverse reactions resulting from the ingestion of insecticides applied to their bodies to prevent insect infestation. For example, cats may foam at the mouth or salivate excessively following the application of certain insecticides. In more severe cases the treated animals may vomit. These adverse reactions can be due to the toxicity of the insecticides which are used for treatment. They also can occur under circumstances where the insecticide preparation poses no problems due to its toxicity, but the animal reacts to the bad taste or smell of the insecticide in an adverse way.
  • Insecticide impregnated collars have been used to prevent infestation of domestic animals with fleas. Many domestic animals, particularly cats, object to wearing collars around their necks, and many pet owners do not like to expose the animal or themselves to the insecticides in the collar. In addition, flea collars are generally less effective in preventing flea infestation than the methods discussed previously. The owners of domestic animals often use the collars to supplement other methods involving direct application of the insecticide to the animal's body. Many of the pesticides commonly used in agricultural and veterinary applications, including the organophosphate compounds are known to be effective for the control of ectoparasites such as fleas. However, these compounds often produce undesirable responses in domestic animals when applied in concentrations and in dosage forms needed to effectively control infestation by fleas .
  • the present invention relates to a method for reducing adverse reactions to an insecticide by an animal in need of administration of insecticide for treating an infestation of parasites. It unexpectedly has been found that applying a dry formulation of an organophosphate insecticide provides an effective and convenient treatment for protecting an animal against infestation by fleas and other ectoparasites, while reducing adverse reactions by the animal to the insecticide.
  • These dry formulations include insecticide-containing microcapsules, which can be applied to one or more limited areas of an animal's body or hair coat. The formulations are effective in inhibiting infestation by ectoparasites for periods of up to two weeks as a result of the controlled release of the insecticide, and they do not cause severe adverse reactions in the treated animals.
  • the invention of the present application relates to high concentration, low volume, substantially dry formulations of insecticides which are effective for the control of fleas and other ectoparasites on animals .
  • Ectoparasites are parasites which live on the exterior parts of an animal's body as distinguished from endoparas tes which live inside the host animal's body. Common ectoparasites include fleas, ticks, lice, mites and flies.
  • the present invention further relates to methods by which these formulations are applied to the animal being treated.
  • Application of the dry formulations of the invention provides effective protection against infestation by ectoparasites while minimizing the number and severity of adverse reactions that can occur following treatment with topical formulations of insecticides .
  • Adverse reactions include reactions which can produce prolonged or lasting toxic effects due to the animal's exposure to a treatment with an insecticide.
  • Suen adverse effects include dermal irritation or other exhibited signs of toxicity, such as heavy salivation or vomiting, which can last for hours or even days after the treatment is applied. In the most severe cases, such adverse reactions can result in the animal' s death.
  • adverse reactions include reactions which can occur even when the animal does not receive a toxic dose of the insecticide, but nonetheless reacts to being exposed to the treatment .
  • adverse reactions include excessive salivation and even vomiting, which occur in response to the taste or smell of the insecticide where the preparation s offensive to the animal.
  • Such adverse reactions are particularly a problem when treating cats because of their natural grooming behavior. Topically applied substances are almost certain to be licked and ingested shortly after they are applied to the animal . When the substance s distasteful or unpleasant, the animal will often salivate immediately and, in more severe cases, it may vomit. Because such reactions generally alarm pet owners and lead to their not repeating treatments for controlling ectoparasites, these reactions also are considered to be adverse reactions, even though they do not result from toxic effects of the insecticides present in the formulations.
  • Pesticides which are useful for the dry formulations of the present invention include compounds of the group known as organophosphates. This group of compounds is known in the art to possess useful pesticidal properties, particularly in the control of fleas on animals.
  • Suitable organophosphate pesticides can include phosphate, phosphothioate or phosphothionate compounds.
  • Preferred pesticides suitable for use in the formulations include the organophosphate compound known as pirimiphos-methyl O- ⁇ 2-diethylamino-6-methylpyri idin-4-yl) o,o-dimethyl phosphorothioate) . Specific examples of organophosphate compounds that can be used in the formulation are listed in Table I. TABLE I
  • dry formulation is used to indicate that the insecticide is prepared such that it contains no more than insignificant or negligible amounts of water.
  • One way in which such a dry formulation can be prepared is to micro-encapsulate the pesticide using organic polyisocyanate intermediates to form a polyurea capsule enclosure around the water-immiscible insecticide.
  • the amount of water in the final preparation will be determined by the ability of the inert ingredients surrounding the microcapsules to hold onto water under the conditions in the drying apparatus used to dry the final microencapsulated preparation. In most cases the amount of water adsorbed onto the inert material is very small such that the formulation is substantially dry.
  • microencapsulation of selected pesticides can be accomplished by the interfacial polymerization of monomer units present in emulsion droplets, which are formed when the water-immiscible pesticide is vigorously mixed with an aqueous solution containing additional polymerizing monomers and heated as discussed in Seaman et al . , "Trends in the Formulation of Pesticides - An Overview, " Pesticide Science 29 (1990) pp. 437-449.
  • the monomers react to form a polymer skin which encapsulates the pesticide and controls its release. Encapsulation can reduce the oral toxicity of the pesticide as much as 100 times over that of non-microencapsulated water based treatments and reduces the dermal toxicity over 10 times that of non-microencapsulated water based treatments .
  • a preferred method of encapsulation of pesticides for use in the treatment of ectoparasite infestation in animals is that disclosed in U.S. Patent No. 4,285,720, the disclosure of which is incorporated herein by reference.
  • the water-immiscible insecticide being encapsulated is dispersed in an aqueous solution which contains suitable surfactants and a protective colloid.
  • suitable surfactants include nonionic, anionic or cationic surfactants having a hydrophile to lipophile balance (HLB) range of from about 12 to about 16.
  • ot suitable surfactants are sodium isopropyl naphthalene sulfonate, polyoxyethylenesorbitol oleate laurate, ethoxylated nonylphenols, and polyethylene glycol ethers of linear alcohols.
  • Preferred surfactants are polyethylene glycol ethers of linear alcohols such as the linear alcohol ethoxylate emulsifier Tergitol 15-S-20.
  • Suitable protective colloids can be selected from a wide range of such materials, including polyacrylates, methyl celluloses, polyvinyl alcohol, polyacrylamide and polymethylvinyl ether/maleic anhydride. The protective colloid can be added to the microencapsulation system either prior to or after the organic dispersion is made.
  • the dry microencapsulated formulations of the invention contain from about 20 to 80% by weight of the active pesticide.
  • One preferred embodiment is a dry microencapsulated formulation containing from about 55 to 75% pirimiphos-methyl .
  • the dry composition of the present application can be applied to a single, limited area on the animal to be treated.
  • the treatment can be applied to two or more specific sites of limited area on the animal.
  • the composition is applied as a single spot to a limited area on the back of the animal between its shoulder blades at a location which the animal is unable to reach with his tongue, so that he is unable to lick or clean the pesticide composition from his coat.
  • composition is used to treat cats, because cats will often salivate or become nauseous after they are exposed to substances they consider distasteful or unpleasant, either orally or by smell. Since the composition is applied topically, it is almost certain to be licked or ingested shortly after it is applied to cats because of their grooming behavior.
  • the quantity of the dry formulation to be applied to an animal is determined by the animal's size and by the concentration of pesticide in the formulation.
  • the compositions can be applied at a dose within a range of about 0.1 gram (g) to about 1.0 g of active compound per kilogram (kg) of the animal's weight.
  • Animals weighing between 5 and 10 pounds (about 2.2 to 4.5 kg) can be treated with a single application of from about 0.3 to about 4 g of the dry formulation, containing from 20 to 90% organophosphate.
  • One preferred treatment comprises applying 0.3 g of a dry formulation containing about 70-75% pirimiphos- methyl per kg of the animal's weight.
  • the dry pesticide formulations of the present invention are useful for controlling fleas and other ectoparasites on animals, particularly smaller animals which are kept as pets, including dogs, cats, rabbits and rodents.
  • the disclosed compositions and methods are particularly advantageous for controlling fleas on cats. Cats are very inefficient at metabolizing pesticides and are, therefore, particularly susceptible to their toxic effects. Additionally, because of their natural grooming behavior, cats are particularly susceptible to reactions due to the unpleasant taste or odor of preparations which are applied to an animals coat or fur.
  • Application of the disclosed compositions by the method of the present invention is essentially non-toxic to cats, and application of the preparations appears to not stimulate the animal to groom immediately after the application.
  • the disclosed methods and compositions also are useful for the control of other insect ns? :, including fleas, lice, ticks and flies, on herd animals such cattle, sheep, goats, horses, donkeys, camels, pigs, reindeer, caribou, and buffalo.
  • Dry encapsulated pirimiphos-methyl was prepared by mixing 1770 g of water with 47.0 g of 40% Reax, 100M sodium lignosulfonate (a poly-protective colloid) and 76.0 g of 20% aqueous Tergitol XD emulsifier in an open reaction vessel with stirring.
  • 2000 g of technical grade pirimiphos-methyl (at least 90% purity) was mixed with 32.0 g of polymethylene polyphenylisocyanate and 130.0 g of tolylene diisocyanate, then added to the aqueous solution in the reaction vessel.
  • An appropriate catalyst such as a basic tertiary organic amine, also can be added to the water-immiscible mixture if desired.
  • the mixture was vigorously stirred using a high shear stirrer to create an oil in water emulsion. After the emulsion was formed and particles of the desired size were obtained, mild agitation was continued for the remainder of the reaction. The temperature of the emulsion was raised to 60°C and the pH of the dispersion was maintained at 8.5 for 3 hours with stirring to allow the interfacial polymerization to proceed to completion. The resulting aqueous suspension of microcapsules was cooled to room temperature.
  • a fragrance such as Alpine MaskTM can be included in the formulation by adding 0.9% of the fragrance to the formulation after encapsulation.
  • microencapsulated dry formulations of pesticides was demonstrated in a dose titration study using a microencapsulated dry formulation of 74% pirimiphos-methyl, which was applied to cats selected from a random population of mixed breed, domestic animals.
  • the animals were housed in individual cages in environmentally controlled rooms and provided with a commercial cat food and water ad libi tum .
  • the animals were divided into four groups of three cats each. Each group received either 1) no treatment; 2) 0.2 grams of the dry formulation of micro-encapsulated 74% pirimiphos-methyl preparation prepared in accordance with the procedures of example 1; 3) 0.3 grams of the preparation or 4) 0.4 grams of the preparation.
  • Each cat was infected with 100 cat fleas, (species Ctenocephalides felis) one day before the microencapsulated preparation was applied.
  • the preparation was applied to the animal's fur or coat as a single spot application to the dorsal neck area of each animal, near the shoulder.
  • the effect of the preparation on reducing or controlling infestation by fleas was determined by monitoring the number of fleas remaining cn the bodies of both treated and untreated animals.
  • the number of fleas remaining on the animals was determined by counting the number of dead fleas found on the pans which covered the bottom of each cage each day and by doing direct body counts on each animal to determine the number of fleas remaining on the animal.
  • the data obtained were used to calculate the percent reduction of fleas in each group using the formula given in Table II.
  • results of the efficacy study indicate that the micro-encapsulated dry formulations reduced infestation on treated animals three days after treatment by 100% when compared with controls. Additionally the one treatment, applied on day 1 protected animals against reinfestation for more than nine days under the conditions employed in the test .
  • the cats were housed individually and provided with a commercial cat food and water ad libi tum. All treatments were applied to the cat's back, on the dorsal thorax near the shoulder blades, one time on Day 0 of the study.
  • the liquid composition of control treatment 3 was applied by pipetting 1 ml aliquots directly onto the animals' skin. Treatments 1 and 2 were briefly rubbed into the cat's coat. The cats were observed continuously for the first hour following the application of the test formulation, at hourly intervals for the next four hours following treatment, then twice daily for the next two days .

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/US1996/018231 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals WO1997018705A2 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
BR9611722-2A BR9611722A (pt) 1995-11-17 1996-11-14 Processo para reduzir reações adversas a um inseticida por um animal e para proteger um animal de infestação por exctoparasitas
SK647-98A SK64798A3 (en) 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals
HU9902703A HUP9902703A2 (hu) 1996-11-14 1996-11-14 Száraz peszticid készítmények állatokon előforduló ektoparaziták írtására
CA 2237334 CA2237334A1 (en) 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals
KR1019980703602A KR19990067579A (ko) 1995-11-17 1996-11-14 동물의 체외 기생충을 방제하기 위한 건성 살충 제형
AU77317/96A AU706884B2 (en) 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals
JP9519791A JP2000500494A (ja) 1995-11-17 1996-11-14 動物に対する外部寄生体を防除する殺虫剤の乾燥配合物
IL12444896A IL124448A0 (en) 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals
EP96940432A EP0862365A2 (en) 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals
PL96328958A PL328958A1 (en) 1995-11-17 1996-11-14 Dry pesticide preparations for fighting against animal ectoparasites
NO982235A NO982235L (no) 1995-11-17 1998-05-15 T°rre preparater fra pesticider for kontroll av ektoparasitter pÕ dyr

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US56003395A 1995-11-17 1995-11-17
US08/560,033 1995-11-17

Publications (2)

Publication Number Publication Date
WO1997018705A2 true WO1997018705A2 (en) 1997-05-29
WO1997018705A3 WO1997018705A3 (en) 1997-07-03

Family

ID=24236075

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/018231 WO1997018705A2 (en) 1995-11-17 1996-11-14 Dry formulations of pesticides for controlling ectoparasites on animals

Country Status (12)

Country Link
EP (1) EP0862365A2 (ja)
JP (1) JP2000500494A (ja)
KR (1) KR19990067579A (ja)
CN (1) CN1253473A (ja)
AU (1) AU706884B2 (ja)
BR (1) BR9611722A (ja)
CZ (1) CZ150098A3 (ja)
IL (1) IL124448A0 (ja)
NO (1) NO982235L (ja)
PL (1) PL328958A1 (ja)
SK (1) SK64798A3 (ja)
WO (1) WO1997018705A2 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003051116A1 (en) * 2001-12-14 2003-06-26 Mars, Incorporated Microencapsulated insecticide
GB2396557A (en) * 2002-11-25 2004-06-30 John Strauss Protecting animals against ectoparasite infestations
CN101856019A (zh) * 2010-06-04 2010-10-13 广东省粮食科学研究所 一种新型储粮害虫缓释杀虫剂及其制备方法
US8263099B2 (en) 2004-03-01 2012-09-11 Sumitomo Chemical Company, Limited Insect growth regulating composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968207A (en) * 1973-12-10 1976-07-06 American Cyanamid Company Method of controlling fleas and ticks on cats and dogs
DE3629714A1 (de) * 1985-09-13 1987-03-19 Bitterfeld Chemie Verfahren zur mikroverkapselung von pestiziden
EP0249409A2 (en) * 1986-06-07 1987-12-16 Coopers Animal Health Limited Liquid Formulations
US4933167A (en) * 1983-07-22 1990-06-12 Scher Herbert B Pesticide compositions
US5292533A (en) * 1992-03-27 1994-03-08 Micro Flo Co. Controlled release microcapsules

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968207A (en) * 1973-12-10 1976-07-06 American Cyanamid Company Method of controlling fleas and ticks on cats and dogs
US4933167A (en) * 1983-07-22 1990-06-12 Scher Herbert B Pesticide compositions
DE3629714A1 (de) * 1985-09-13 1987-03-19 Bitterfeld Chemie Verfahren zur mikroverkapselung von pestiziden
EP0249409A2 (en) * 1986-06-07 1987-12-16 Coopers Animal Health Limited Liquid Formulations
US5292533A (en) * 1992-03-27 1994-03-08 Micro Flo Co. Controlled release microcapsules

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003051116A1 (en) * 2001-12-14 2003-06-26 Mars, Incorporated Microencapsulated insecticide
GB2396557A (en) * 2002-11-25 2004-06-30 John Strauss Protecting animals against ectoparasite infestations
US8263099B2 (en) 2004-03-01 2012-09-11 Sumitomo Chemical Company, Limited Insect growth regulating composition
CN101856019A (zh) * 2010-06-04 2010-10-13 广东省粮食科学研究所 一种新型储粮害虫缓释杀虫剂及其制备方法

Also Published As

Publication number Publication date
PL328958A1 (en) 1999-03-01
SK64798A3 (en) 1998-12-02
JP2000500494A (ja) 2000-01-18
AU7731796A (en) 1997-06-11
EP0862365A2 (en) 1998-09-09
AU706884B2 (en) 1999-07-01
NO982235D0 (no) 1998-05-15
WO1997018705A3 (en) 1997-07-03
BR9611722A (pt) 1999-12-28
NO982235L (no) 1998-07-13
IL124448A0 (en) 1998-12-06
CN1253473A (zh) 2000-05-17
KR19990067579A (ko) 1999-08-25
CZ150098A3 (cs) 1998-09-16

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