CA2848889C - Improved ectoparasiticidal formulations - Google Patents
Improved ectoparasiticidal formulations Download PDFInfo
- Publication number
- CA2848889C CA2848889C CA2848889A CA2848889A CA2848889C CA 2848889 C CA2848889 C CA 2848889C CA 2848889 A CA2848889 A CA 2848889A CA 2848889 A CA2848889 A CA 2848889A CA 2848889 C CA2848889 C CA 2848889C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- ectoparasiticidal
- animal
- solvent
- crystallization inhibitor
- 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.)
- Expired - Fee Related
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- 238000009472 formulation Methods 0.000 title abstract description 23
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- 239000005899 Fipronil Substances 0.000 claims abstract description 38
- 229940013764 fipronil Drugs 0.000 claims abstract description 38
- 238000002425 crystallisation Methods 0.000 claims abstract description 31
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- 239000003960 organic solvent Substances 0.000 claims abstract description 23
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- 244000078703 ectoparasite Species 0.000 claims abstract description 12
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- HVQHXBNMBZJPLK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methylprop-2-en-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound CC(=C)CNC1=C([S+]([O-])C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HVQHXBNMBZJPLK-UHFFFAOYSA-N 0.000 description 1
- LWWDYSLFWMWORA-BEJOPBHTSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-4-(trifluoromethylsulfanyl)pyrazole-3-carbonitrile Chemical compound c1cc(O)c(OC)cc1\C=N\c1c(SC(F)(F)F)c(C#N)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl LWWDYSLFWMWORA-BEJOPBHTSA-N 0.000 description 1
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- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
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- 239000005941 Thiamethoxam Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- 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
- A01N25/22—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 ingredients stabilising the active ingredients
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, 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
- A01N47/02—Biocides, 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 no bond to a nitrogen atom
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361812905P | 2013-04-17 | 2013-04-17 | |
| US61/812,905 | 2013-04-17 | ||
| US14/242,226 | 2014-04-01 | ||
| US14/242,226 US8993613B2 (en) | 2013-04-17 | 2014-04-01 | Ectoparasiticidal formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2848889A1 CA2848889A1 (en) | 2014-10-17 |
| CA2848889C true CA2848889C (en) | 2017-04-11 |
Family
ID=51729481
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2848889A Expired - Fee Related CA2848889C (en) | 2013-04-17 | 2014-04-15 | Improved ectoparasiticidal formulations |
| CA2848888A Abandoned CA2848888A1 (en) | 2013-04-17 | 2014-04-15 | Improved ectoparasiticidal methods |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2848888A Abandoned CA2848888A1 (en) | 2013-04-17 | 2014-04-15 | Improved ectoparasiticidal methods |
Country Status (5)
| Country | Link |
|---|---|
| US (6) | US9049860B2 (enExample) |
| EP (1) | EP2986109B1 (enExample) |
| JP (1) | JP6118946B2 (enExample) |
| CA (2) | CA2848889C (enExample) |
| WO (1) | WO2014172186A2 (enExample) |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2716453B1 (fr) | 1994-02-22 | 1996-03-29 | Rhone Poulenc Agrochimie | Procédé de sulfinylation de composés hétérocycliques. |
| US6426333B1 (en) | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| JPH0813721B2 (ja) * | 1986-06-27 | 1996-02-14 | ジーエイエフ・コーポレーション | 農業用乳剤組成物 |
| FR2673075B1 (fr) * | 1991-02-22 | 1998-12-31 | Rhone Poulenc Chimie | Microemulsions de pyrethrouides et leur utilisation. |
| JP3715994B2 (ja) | 1993-12-21 | 2005-11-16 | 住友化学株式会社 | 害虫防除剤 |
| JPH07242510A (ja) * | 1994-01-13 | 1995-09-19 | Nippon Nohyaku Co Ltd | 除草剤組成物 |
| IL116148A (en) * | 1994-11-30 | 2001-03-19 | Rhone Poulenc Agrochimie | Complexible composition for insect control |
| DE4443888A1 (de) | 1994-12-09 | 1996-06-13 | Bayer Ag | Dermal applizierbare Formulierungen von Parasitiziden |
| FR2739255B1 (fr) | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| JPH09249502A (ja) * | 1996-03-15 | 1997-09-22 | Nissan Chem Ind Ltd | 改良された固形農薬組成物 |
| US6010710A (en) | 1996-03-29 | 2000-01-04 | Merial | Direct pour-on skin solution for antiparasitic use in cattle and sheep |
| IE80657B1 (en) | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
| AU3499297A (en) * | 1996-08-12 | 1998-03-06 | Isp Investments Inc. | Stabilizer additive for agchemical tank mix |
| US6001658A (en) | 1996-09-13 | 1999-12-14 | Diagnostic Chemicals Limited | Test strip apparatus and method for determining presence of analyte in a fluid sample |
| US6998131B2 (en) | 1996-09-19 | 2006-02-14 | Merial Limited | Spot-on formulations for combating parasites |
| FR2761232B1 (fr) | 1997-03-26 | 2000-03-10 | Rhone Merieux | Procede et moyens d'eradication des puces dans les locaux habites par les petits mammiferes |
| US6117854A (en) | 1997-08-20 | 2000-09-12 | The Clorox Company | Enhanced performance insecticide compositions containing plant derived oil carriers and methods of using the same |
| US6090751A (en) * | 1998-06-10 | 2000-07-18 | Rhone-Poulenc Agro | Emulsifiable concentrate comprising an insecticidal 1-arylpyrazole |
| US6045816A (en) * | 1998-06-17 | 2000-04-04 | Isp Investments Inc. | Water-based microemulsion of a pyrethroid |
| ES2222743T3 (es) | 1999-10-22 | 2005-02-01 | Bayer Cropscience S.A. | Procedimiento para preparar un derivado 4-trifluorometilsulfinilpirazol. |
| RU2291863C2 (ru) | 2000-06-09 | 2007-01-20 | Байер Кропсайенс С.А. | Способ получения пестицидных соединений |
| US6718442B1 (en) | 2000-07-20 | 2004-04-06 | Silicon Graphics, Inc. | Method and system for using high count invalidate acknowledgements in distributed shared memory systems |
| DE10146873A1 (de) | 2001-09-24 | 2003-04-17 | Bayer Cropscience Gmbh | Heterocyclische Amide und -Iminderivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
| LT1610613T (lt) | 2003-04-04 | 2017-03-27 | Merial, Inc. | Vietinio taikymo antihelmintinės veterinarinės kompozicijos |
| US7531186B2 (en) * | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
| JP5710877B2 (ja) * | 2006-04-28 | 2015-04-30 | シーバ アニマル ヘルス リミテッド ライアビリティ カンパニー | ピレスロイドを含有する高濃度局所殺虫剤 |
| BRPI0813031A2 (pt) | 2007-07-30 | 2014-10-07 | Du Pont | "método de controle ou prevenção de maturação de pulgas" |
| CA2698528C (en) | 2007-09-06 | 2013-01-08 | The Hartz Mountain Corporation | Animal parasite-control method using insect growth regulators |
| FR2922108A1 (fr) * | 2007-10-11 | 2009-04-17 | Virbac Sa | Utilisation d'un derive de 1-n-(halo-3-pyridylmethyle)-n-methylamino-1-alkylamino -2- nitroethylene pour la preparation d'une composition pharmaceutique veterinaire pour lutter contre les puces |
| GB0905365D0 (en) * | 2009-03-27 | 2009-05-13 | Norbrook Lab Ltd | A topical parasiticide composition |
| AR079426A1 (es) | 2009-11-20 | 2012-01-25 | Sumitomo Chemical Co | Composicion de control de plagas |
| JP2015131776A (ja) | 2014-01-10 | 2015-07-23 | 住友化学株式会社 | 動物外部寄生虫防除組成物 |
-
2014
- 2014-04-01 US US14/242,178 patent/US9049860B2/en active Active
- 2014-04-01 US US14/242,226 patent/US8993613B2/en active Active
- 2014-04-11 WO PCT/US2014/033713 patent/WO2014172186A2/en not_active Ceased
- 2014-04-11 EP EP14785698.3A patent/EP2986109B1/en not_active Not-in-force
- 2014-04-11 JP JP2016508972A patent/JP6118946B2/ja not_active Expired - Fee Related
- 2014-04-15 CA CA2848889A patent/CA2848889C/en not_active Expired - Fee Related
- 2014-04-15 CA CA2848888A patent/CA2848888A1/en not_active Abandoned
-
2015
- 2015-01-22 US US14/602,901 patent/US9247733B2/en active Active
- 2015-12-07 US US14/960,714 patent/US20160081330A1/en not_active Abandoned
-
2016
- 2016-08-11 US US15/234,143 patent/US9955696B2/en active Active
-
2018
- 2018-04-09 US US15/947,940 patent/US10064411B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8993613B2 (en) | 2015-03-31 |
| US20170000131A1 (en) | 2017-01-05 |
| US20140315969A1 (en) | 2014-10-23 |
| US9049860B2 (en) | 2015-06-09 |
| WO2014172186A2 (en) | 2014-10-23 |
| WO2014172186A3 (en) | 2015-01-29 |
| US10064411B1 (en) | 2018-09-04 |
| US20140315970A1 (en) | 2014-10-23 |
| JP6118946B2 (ja) | 2017-04-19 |
| US20150157013A1 (en) | 2015-06-11 |
| EP2986109A2 (en) | 2016-02-24 |
| JP2016521271A (ja) | 2016-07-21 |
| EP2986109A4 (en) | 2016-12-07 |
| CA2848889A1 (en) | 2014-10-17 |
| US9955696B2 (en) | 2018-05-01 |
| CA2848888A1 (en) | 2014-10-17 |
| US9247733B2 (en) | 2016-02-02 |
| US20160081330A1 (en) | 2016-03-24 |
| EP2986109B1 (en) | 2018-09-19 |
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Legal Events
| Date | Code | Title | Description |
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| MKLA | Lapsed |
Effective date: 20220301 |
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| MKLA | Lapsed |
Effective date: 20200831 |