FR2746597A1 - Association insecticide contre les puces des mammiferes, notamment des chiens et chats - Google Patents
Association insecticide contre les puces des mammiferes, notamment des chiens et chats Download PDFInfo
- Publication number
- FR2746597A1 FR2746597A1 FR9703711A FR9703711A FR2746597A1 FR 2746597 A1 FR2746597 A1 FR 2746597A1 FR 9703711 A FR9703711 A FR 9703711A FR 9703711 A FR9703711 A FR 9703711A FR 2746597 A1 FR2746597 A1 FR 2746597A1
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- France
- Prior art keywords
- alkyl
- haloalkyl
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- compound
- radical
- 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.)
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- 241000490513 Ctenocephalides canis Species 0.000 title 1
- 241000258924 Ctenocephalides felis Species 0.000 title 1
- 230000000749 insecticidal effect Effects 0.000 title 1
- 230000000699 topical effect Effects 0.000 title 1
- 150000001875 compounds Chemical group 0.000 claims abstract description 93
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 50
- 125000005843 halogen group Chemical group 0.000 claims abstract description 46
- -1 4,5-dicyano-imidazol-2-yl Chemical group 0.000 claims abstract description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 239000012530 fluid Substances 0.000 claims abstract description 9
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 241000238631 Hexapoda Species 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 241001465754 Metazoa Species 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
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- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 2
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229930191400 juvenile hormones Natural products 0.000 claims description 2
- 229930001540 kinoprene Natural products 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- ZHALDANPYXAMJF-UHFFFAOYSA-N octadecanoate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCCCCCCC([O-])=O ZHALDANPYXAMJF-UHFFFAOYSA-N 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 229950008882 polysorbate Drugs 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 2
- ITCAUAYQCALGGV-XTICBAGASA-M sodium;(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Na+].C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O ITCAUAYQCALGGV-XTICBAGASA-M 0.000 claims description 2
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 claims description 2
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 235000010356 sorbitol Nutrition 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims description 2
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 claims description 2
- 229940029614 triethanolamine stearate Drugs 0.000 claims description 2
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002500 effect on skin Effects 0.000 claims 2
- 230000007774 longterm Effects 0.000 claims 2
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 claims 1
- WGZYVHFXLPDNDL-UHFFFAOYSA-N 4-benzoyl-2-phenylpyrazole-3-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)C(=C1C#N)C=NN1C1=CC=CC=C1 WGZYVHFXLPDNDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005927 Pyriproxyfen Substances 0.000 claims 1
- CGCOVQSKNBEYNN-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(C(F)(F)F)C=C1 CGCOVQSKNBEYNN-UHFFFAOYSA-N 0.000 claims 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 4
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 abstract 1
- 241000118205 Ovicides Species 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 12
- 239000005899 Fipronil Substances 0.000 description 12
- 241000258242 Siphonaptera Species 0.000 description 12
- 229940013764 fipronil Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 5
- 239000002297 parasiticide Substances 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 210000004209 hair Anatomy 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000258922 Ctenocephalides Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001399426 Myas Species 0.000 description 1
- SBKMRXDBQFVGJW-UHFFFAOYSA-N NC(=O)NC1=CC=C(OC(F)(F)C(F)F)C=C1F Chemical compound NC(=O)NC1=CC=C(OC(F)(F)C(F)F)C=C1F SBKMRXDBQFVGJW-UHFFFAOYSA-N 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000718000 Pulex irritans Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001414987 Strepsiptera Species 0.000 description 1
- 241000353223 Xenopsylla cheopis Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000036576 dermal application Effects 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940001474 sodium thiosulfate Drugs 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- 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
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Toxicology (AREA)
- Birds (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
US-A-5 439 924, des composés à effet ovicide et/ou larvicide pour les stades immatures de divers ectoparasites. Parmi ces composé (IGR) figurent des composés régulateurs de croissance des insectes agissant soit en bloquant le développement des stades immatures (oeufs et larves) en stades adultes, soit en inhibant la synthèse de la chitine.
dans laquelle
R1 est CN ou méthyle ou un atome d'halogène
R2 est S(O)nR3 ou 4,5-dicyanoimidazol 2-yl ou haloalkyle ;
R3 est alkyle ou haloalkyle ;
R4 représente un atome d'hydrogène ou d'halogène ; ou un radical NR6, S(O)mR7, C(O)R7, C(O)O-R7, aikyle, haloalkyle ou OR8 ou un radical -N=C(R9) (R10) ;
R5 et R6 représentent indépendamment l'atome d'hydrogène ou un radical aikyle, haloalkyle, C(O)alkyle, alcoxycarbonyl, S(O)r-CF3 ; ou R5 et R6 peuvent former ensemble un radical alkylène divalent qui peut être interrompu par un ou deux hétéroatomes divalents tels que l'oxygène ou le soufre
R7 représente un radical alkyle ou haloalkyle ;
R8 représente un radical alkyle, haloalkyle ou un atome d'hydrogène
R9 représente un radical alkyle ou un atome d'hydrogène
Rso représente un groupe phényl ou hétéroaryle éventuellement substitué par un ou plusieurs atome d'halogène ou groupes tels que OH, -O-alkyle, S-alkyle, cyano, ou alkyle ;
R11 et R12 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou d'halogène ou éventuellement CN ou NO2 ;
R13 représente un atome d'halogène ou un groupe haloalkyle, haloalkoxy, S(O)qCF3 ou SF5
m, n, q, r représentent, indépendamment l'un de l'autre, un nombre entier égal à 0, 1 ou 2 ;
X représente un atome d'azote trivalent ou un radical C-R12, les trois autres valences de l'atome de carbone faisant partie du cycle aromatique
sous réserve que, lorsque R1 est méthyle, soit R3 est haloalkyle, R4 est NH2, R11 est Cl, R13 est CF3, et X est N ; soit R2 est 4,5-dicyanoimidazol 2-yl, R4 est
Cl, R11 est Cl, R13 est CF3 et X est =C-Cl ;
et d'autre part, d'au moins un composé (B), de type IGR (régulateur de croissance d'insectes), dans un véhicule fluide acceptable pour l'animal et convenable pour une application cutanée locale.
R1 est CN ou méthyle
R2 est S(O)nR3
R3 est alkyle ou haloalkyle
R4 représente un atome d'hydrogène ou d'halogène ; ou un radical NR5R6, S(O)R7, C(O)R7, alkyle, haloalkyle ou OR8 ou un radical -N=C(R9) (R10)
R5 et R6 représentent indépendamment l'atome d'hydrogène ou un radical alkyle, haloalkyle, C(O)alkyle, S(O)r-CF3 ; ou R5 et R6 peuvent former ensemble un radical alkylène divalent qui peut être interrompu par un ou deux hétéroatomes divalents tels que l'oxygène ou le soufre
R7 représente un radical alkyle ou haloalkyle
R8 représente un radical alkyle, haloalkyle ou un atome d'hydrogène
R9 représente un radical alkyle ou un atome d'hydrogène
R10 représente un groupe phényl ou hétéroaryle éventuellement substitué par un ou plusieurs atomes d'halogène ou groupes tels que OH, -0-aikyle, S-alkyle, cyano, ou alkyle
R11 et R12 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou d'halogène
R13 représente un atome d'halogène ou un groupe haloalkyle, haloalkoxy, S(O)qCF3 ou SFs
m, n, q, r représentent, indépendamment l'un de l'autre, un nombre entier égal à 0, 1 ou 2
X représente un atome d'azote trivalent ou un radical C-R12, les trois autres valences de l'atome de carbone faisant partie du cycle aromatique
sous réserve que, lorsque R1 est méthyle, alors R3 est haloalkyle, R4 est NH2, R11 est Cl, R13 est
CF3, et X est N.
R3 est haloalkyle, R4 est NH2, R11 et R12 sont indépendamment l'un de l'autre un atome d'halogène, et/ou R13 est haloalkyle.
CF3phényl]3-CN 4-[SO-CF3] 5-NH2 pyrazole, dont la dénomination commune est fipronil.
1- n = 0, R3 = CF3
2- n = 1, R3 = éthyle.
azadirachtin - Agridyne
diofenolan (Ciba Geigy)
fenoxycarb (Ciba Geigy)
hydroprene (Sandoz)
kinoprene (Sandoz)
methoprene (Sandoz)
pyriproxyfene (Sumitomo/Mgk)
tetrahydroazadirachtin (Agridyne)
et le 4-chloro-2-(2-chloro-2-méthylpropyl)-5 (6-iodo-3-pyridylméthoxy)pyridizine-3(2H)-one et les inhibiteurs de la synthèse de la chitine, notamment
chlorfluazuron (Ishihara Sangyo)
cyromazine (Ciba Geigy)
diflubenzuron (Solvay Duphar)
fluazuron (Ciba Geigy)
flucycloxuron (Solvay Duphar)
flufenoxuron (Cyanamid)
hexaflumuron (Dow Elanco)
lufenuron (Ciba Geigy)
tebufenozide (Rohm & Haas)
teflubenzuron (Cyanamid)
triflumuron (Bayer) ces composés étant définis par leur dénomination commune internationale (The Pesticide Manual, îOth edition, 1994,
Ed. Clive Tomlin, Grande-Bretagne).
R1 est CN ou méthyle
R2 est S(O)R3
R3 est alkyle ou haloalkyle
R4 représente un atome d'hydrogène ou d'halogène ; ou un radical NR6, S < O)1R7, C(O)R7, aikyle, haloalkyle ou OR8 ou un radical -N=C(R9) (R10)
R5 et R6 représentent indépendamment l'atome d'hydrogène ou un radical alkyle, haloalkyle, C(O)alkyle, S(O)r-CF3 ; ou R5 et R6 peuvent former ensemble un radical alkylène divalent qui peut être interrompu par un ou deux hétéroatomes divalents tels que l'oxygène ou le soufre
R7 représente un radical alkyle ou haloalkyle
R8 représente un radical alkyle, haloalkyle ou un atome d'hydrogène
R9 représente un radical alkyle ou un atome d'hydrogène
R10 représente un groupe phényl ou hétéroaryle éventuellement substitué par un ou plusieurs atomes d'halogène ou groupes tels que OH, -O-alkyle, 5-aikyle, cyano, ou alkyle
R11 et R12 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou d'halogène
R13 représente un atome d'halogène ou un groupe haloalkyle, haloalkoxy, S(O)qCF3 ou SFs
m, n, q, r représentent, indépendamment l'un de 1autre, un nombre entier égal à 0, 1 ou 2
X représente un atome d'azote trivalent ou un radical C-R12, les trois autres valences de l'atome de carbone faisant partie du cycle aromatique
sous réserve que, lorsque RI est méthyle, alors R3 est haloalkyle, R4 est NH2, R11 est Cl, R13 est
CF3, et X est N.
O, R3 étant de préférence CF3, ainsi que ceux dans lesquels X = C-R12, R12 étant un atome d'halogène. On préfère aussi les composés dans lesquels R11 est un atome d'halogène ainsi que ceux dans lesquels R13 est haloalkyle, de préférence CF3. Dans le cadre de la présente invention, on retiendra avantageusement les composés réunissant deux ou plusieurs de ces caractéristiques.
R3 est haloalkyle, R4 est NH2, R11 et R12 sont indépendamment l'un de l'autre un atome d'halogène et/ou R13 est haloalkyle.
1- n = 0, R3 = CF3
2- n = 1, R3 = éthyle.
b) un inhibiteur de cristallisation, notamment présent à raison de 1 à 20 % (P/V), de préférence de 5 à 15 % cet inhibiteur répondant au test selon lequel 0,3 ml d'une solution A comprenant 10 % (P/V) du composé de formule (I) dans le solvant défini sous c) ci-après, ainsi que 10 % de cet inhibiteur, sont déposés sur une lame de verre à 200C pendant 24 heures, à la suite de quoi on observe à l'oeil nu peu ou pas de cristaux, notamment moins de 10 cristaux, de préférence 0 cristaux, sur la lame de verre,
c) un solvant organique ayant une constante diélectrique comprise entre 10 et 35, de préférence entre 20 et 30, la teneur de ce solvant c) dans la composition globale représentant de préférence le complément à 100 % de la composition,
d) un cosolvant organique ayant un point d'ébullition inférieur à 1000C, de préférence inférieur à 800C et ayant une constante diélectrique comprise entre 10 et 40, de préférence entre 20 et 30 ; ce cosolvant peut avantageusement être présent dans la composition selon un ratio poids/poids (P/P) de d)/c) compris entre 1/15 et 1/2. Le solvant est volatil afin de servir notamment de promoteur de séchage et est miscible à l'eau et/ou au solvant c).
- la polyvinylpyrrolidone, les alcools polyvinyliques, les copolymères d'acétate de vinyle et de vinylpyrrolidone, les polyéthylèneglycols, l'alcool benzylique, le mannitol, le glycérol, le sorbitol, les esters de sorbitane polyoxyéthylénés ; la lécithine, la carboxyméthylcellulose sodique, les dérivés acryliques tels que méthacrylates et autres,
- les tensioactifs anioniques tels que les stéarates alcalins, notamment de sodium, de potassium ou d'ammonium ; le stéarate de calcium ; le stéarate de triéthanolamine ; l'abiétate de sodium ; les sulfates d'alkyle, notamment le laurylsulfate de sodium et le cétylsulfate de sodium ; le dodécylbenzènesulfonate de sodium, le dioctylsulfosuccinate de sodium ; les acides gras, notamment ceux dérivés de l'huile de coprah,
- les tensioactifs cationiques tels que les sels d'ammonium quaternaires hydrosolubles de formule N+R'R"R'"R"",Y- dans laquelle les radicaux R sont des radicaux hydrocarbonés, éventuellement hydroxylés, et Y est un anion d'un d'acide fort tel que les anions halogénure, sulfate et sulfonates ; le bromure de cétyltriméthylammonium fait partie des tensioactifs cationiques utilisables,
- les sels d'amine de formule N+R'R"R"' dans laquelle les radicaux R sont des radicaux hydrocarbonés, éventuellement hydroxylés ; le chlorhydrate d'octadécylamine fait partie des tensioactifs cationiques utilisables,
- les tensioactifs non ioniques tels que les esters de sorbitane, éventuellement polyoxyéthylénés, en particulier Polysorbate 80, les éthers d'alkyle polyoxyéthylénés ; le stéarate de polyéthylèneglycol, les dérivés polyoxyéthylénés de l'huile de ricin, les esters de polyglycérol, les alcools gras polyoxyéthylénés, les acides gras polyoxyéthylénés, les copolymères d'oxyde d'éthylène et d'oxyde de propylène,
- les tensioactifs amphotères tels que les composés lauryle substitués de la betaïne,
ou de préférence un mélange d'au moins deux d'entre eux.
- les différents grades de polyvinylpyrrolidone,
- les alcools polyvinyliques, et
- les copolymères d'acétate de vinyle et de vinylpyrrolidone.
Polysorbate, par exemple le Polysorbate 80.
fipronil 10 %
pyriproxyphène 5 %
Exemple 2
fipronil 5 %
pyriproxyphène 5 %
Exemple 3
fipronil 5 %
pyriproxyphène 20 %
Exemple 4
fipronil 10 %
méthoprène 30 %
Exemple 5
fipronil 10 % 1- < 2, 6-difluorobenzoyl)-3-(2-fluoro-4- trifluorométhyl)phénuylurée 5 %.
Claims (34)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9703711A FR2746597B1 (fr) | 1996-03-29 | 1997-03-26 | Association insecticide contre les puces des mammiferes, notamment des chiens et chats |
US08/863,692 US6096329A (en) | 1996-03-29 | 1997-05-27 | Insecticidal combination to control mammal fleas, in particular fleas on cats and dogs |
US10/052,597 US6685954B2 (en) | 1996-03-29 | 2002-01-17 | Insecticidal combination to control mammal fleas, in particular fleas on cats and dogs |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9604208A FR2746594B1 (fr) | 1996-03-29 | 1996-03-29 | Association insecticide contre les puces des mammiferes, notamment des chiens et chats |
US69211396A | 1996-08-05 | 1996-08-05 | |
FR9703711A FR2746597B1 (fr) | 1996-03-29 | 1997-03-26 | Association insecticide contre les puces des mammiferes, notamment des chiens et chats |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2746597A1 true FR2746597A1 (fr) | 1997-10-03 |
FR2746597B1 FR2746597B1 (fr) | 1998-11-06 |
Family
ID=26232631
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR9703711A Expired - Lifetime FR2746597B1 (fr) | 1996-03-29 | 1997-03-26 | Association insecticide contre les puces des mammiferes, notamment des chiens et chats |
Country Status (33)
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US (2) | US6096329A (fr) |
JP (2) | JP3702965B2 (fr) |
CN (2) | CN1185716A (fr) |
AR (2) | AR006522A1 (fr) |
AT (1) | AT503376B1 (fr) |
AU (1) | AU731994B2 (fr) |
BE (1) | BE1010478A5 (fr) |
BR (1) | BR9702150B1 (fr) |
CA (2) | CA2221418C (fr) |
CH (1) | CH692893A8 (fr) |
CL (1) | CL2004001187A1 (fr) |
CZ (1) | CZ296852B6 (fr) |
DE (15) | DE19782317A5 (fr) |
DK (1) | DK177397B1 (fr) |
ES (1) | ES2137889B1 (fr) |
FI (2) | FI122468B (fr) |
FR (1) | FR2746597B1 (fr) |
GB (1) | GB2317564B (fr) |
GR (1) | GR1002898B (fr) |
HU (2) | HU229890B1 (fr) |
IE (1) | IE80657B1 (fr) |
IL (1) | IL122117A (fr) |
IT (1) | IT1291701B1 (fr) |
LU (2) | LU90176B1 (fr) |
MX (1) | MX9709091A (fr) |
NL (2) | NL1005676C2 (fr) |
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PL (2) | PL204043B1 (fr) |
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