CN1185716A - 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 - Google Patents
防治哺乳动物、特别是狗和猫蚤的杀虫组合物 Download PDFInfo
- Publication number
- CN1185716A CN1185716A CN97190271A CN97190271A CN1185716A CN 1185716 A CN1185716 A CN 1185716A CN 97190271 A CN97190271 A CN 97190271A CN 97190271 A CN97190271 A CN 97190271A CN 1185716 A CN1185716 A CN 1185716A
- Authority
- CN
- China
- Prior art keywords
- composition
- alkyl
- compound
- haloalkyl
- represent
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 241000124008 Mammalia Species 0.000 title claims abstract description 12
- 241000282326 Felis catus Species 0.000 title claims description 9
- 241000282472 Canis lupus familiaris Species 0.000 title 1
- 230000000749 insecticidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 241001465754 Metazoa Species 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 14
- 241000238631 Hexapoda Species 0.000 claims abstract description 7
- 239000012530 fluid Substances 0.000 claims abstract description 6
- 239000003630 growth substance Substances 0.000 claims abstract description 6
- 230000000699 topical effect Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000001188 haloalkyl group Chemical group 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 239000002585 base Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- -1 phenmethylol Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 22
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 18
- 239000003112 inhibitor Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 239000005927 Pyriproxyfen Substances 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 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 description 9
- 239000002904 solvent Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003093 cationic surfactant Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000006184 cosolvent Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 230000000590 parasiticidal effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- 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 claims description 5
- 102000002322 Egg Proteins Human genes 0.000 claims description 5
- 108010000912 Egg Proteins Proteins 0.000 claims description 5
- 239000005912 Lufenuron Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 230000008029 eradication Effects 0.000 claims description 5
- FYQGBXGJFWXIPP-UHFFFAOYSA-N hydroprene Chemical compound CCOC(=O)C=C(C)C=CCC(C)CCCC(C)C FYQGBXGJFWXIPP-UHFFFAOYSA-N 0.000 claims description 5
- 229930000073 hydroprene Natural products 0.000 claims description 5
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 5
- 229960000521 lufenuron Drugs 0.000 claims description 5
- 229930002897 methoprene Natural products 0.000 claims description 5
- 229950003442 methoprene Drugs 0.000 claims description 5
- 210000004681 ovum Anatomy 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 4
- 229920002101 Chitin Polymers 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 235000010356 sorbitol Nutrition 0.000 claims description 4
- 239000005878 Azadirachtin Substances 0.000 claims description 3
- 125000006414 CCl Chemical group ClC* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 claims description 3
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 claims description 3
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 claims description 3
- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 claims description 3
- 229950006719 fluazuron Drugs 0.000 claims description 3
- 229930014550 juvenile hormone Natural products 0.000 claims description 3
- 239000002949 juvenile hormone Substances 0.000 claims description 3
- 150000003633 juvenile hormone derivatives Chemical class 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- FZRBKIRIBLNOAM-UHFFFAOYSA-N (E,E)-2-propynyl 3,7,11-trimethyl-2,4-dodecadienoate Chemical compound CC(C)CCCC(C)CC=CC(C)=CC(=O)OCC#C FZRBKIRIBLNOAM-UHFFFAOYSA-N 0.000 claims description 2
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 claims description 2
- ODCMOZLVFHHLMY-UHFFFAOYSA-N 1-(2-hydroxyethoxy)hexan-2-ol Chemical compound CCCCC(O)COCCO ODCMOZLVFHHLMY-UHFFFAOYSA-N 0.000 claims description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 claims description 2
- ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 claims description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000005893 Diflubenzuron Substances 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- NWQXYQUFNNDNES-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] NWQXYQUFNNDNES-UHFFFAOYSA-N 0.000 claims description 2
- 239000005937 Tebufenozide Substances 0.000 claims description 2
- 239000005938 Teflubenzuron Substances 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 2
- 235000013539 calcium stearate Nutrition 0.000 claims description 2
- 239000008116 calcium stearate Substances 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 229940110456 cocoa butter Drugs 0.000 claims description 2
- 235000019868 cocoa butter Nutrition 0.000 claims description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 2
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims description 2
- 229940019503 diflubenzuron Drugs 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 2
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 2
- 229940100242 glycol stearate Drugs 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 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
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 238000004088 simulation Methods 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
- 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
- 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
- 125000004432 carbon atom Chemical class C* 0.000 claims 3
- 230000001681 protective effect Effects 0.000 claims 3
- 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 abstract description 14
- 239000005899 Fipronil Substances 0.000 abstract description 14
- 229940013764 fipronil Drugs 0.000 abstract description 14
- 239000002917 insecticide Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 description 13
- 241000490513 Ctenocephalides canis Species 0.000 description 5
- 241000258924 Ctenocephalides felis Species 0.000 description 5
- 239000002297 parasiticide Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001721 carbon Chemical class 0.000 description 4
- 210000004209 hair Anatomy 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 241000258242 Siphonaptera Species 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 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
- 241000718000 Pulex irritans Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000003071 parasitic 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
- 210000002268 wool Anatomy 0.000 description 2
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 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
- 241000196324 Embryophyta Species 0.000 description 1
- 241001248531 Euchloe <genus> Species 0.000 description 1
- 241001397515 Leptopsylla segnis Species 0.000 description 1
- 241000256626 Pterygota <winged insects> Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 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
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000003054 hormonal effect Effects 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000003403 methoprene group Chemical group 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 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
- 208000024891 symptom Diseases 0.000 description 1
- 239000011885 synergistic combination Substances 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
- 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
- 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
- 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
Abstract
特别是防治小哺乳动物身上的蚤的方法和组合物,其特征在于在动物可接受的和适于局部皮肤涂敷,优选地限于一块小表面涂敷的流体赋形剂中,这种组合物含有至少一种1-N-芳基吡唑杀虫剂,具体是fipronil,和至少一种IGR(昆虫生长调节剂)类型化合物,所述杀虫剂和所述化合物的剂量和比例对蚤具有杀虫的功效。
Description
本发明涉及防治哺乳动物,特别是狗和猫蚤的方法的改进。本发明还涉及以已知的杀寄生虫剂协同组合为基础的、用于这种用途的新组合物。最后,本发明还涉及这样一些已知杀寄生虫剂应在制备这种组合物方面的用途。
在EP-A-295217和EP-A-352944中描述了以1-N-芳基吡唑为主要成分的一组新的杀虫剂。在这些专利中所限定的这些组的化合物是极富活性的,这些化合物中的一种化合物1-(2,6-Cl2-4-CF3-苯基)-3-CN-4-(SO-CF3)-5-NH2-吡唑,其通用名是fipronil,不仅对培养的寄生虫,而且对哺乳动物的外-寄生虫,特别是包括,但不仅限于蚤、蜱、飞虫和蝇蛆(myase),都是特别有效的。
例如由US-A-5439924专利已经知道,一些化合物具有杀卵的效果和/或对各种不同的幼龄外-寄生虫具有杀幼虫的效果。在这些化合物中,(IGR)表示昆虫生长调节剂化合物,这些化合物或者以阻断幼龄虫生长(卵和幼虫)成成龄虫,或者通过抑制几丁质合成的方式发挥作用。
另外,人们还由FR-A-2713889专利知道,该专利一般性地描述了至少一种IGR(昆虫生长调节剂)类型化合物与三种N-芳基二唑中的至少一种化合物的组合,IGR类型化合物包括具有保幼激素活性的化合物和合成几丁质的抑制剂,N-芳基二唑具体是fipronil,用于防治属于不同目的各种害虫。
这些组合物能够以各种不同的形式使用,却没有明确指出,这些不同的形式用于例如家畜的、卫生的或植物检疫中的哪一类应用,也没有明确指出这些不同的形式分别针对哪一类寄生虫。
可以想到的兽医唯一应用是与生产一种杀虫项圈、缓慢盐析配方实例相关的。
本发明提出改进防治小哺乳动物,特别是狗和猫身上的蚤的方法。
本发明具体目的是使用已知的杀寄生虫剂,制备一种对这些动物的蚤极富活性的组合物。
最后,本发明的目的是一种如此制备的、具体用于防治这些蚤的新组合物。
关于本发明意义上的蚤,应当理解为蚤目中任何种类的常见或不常见的寄生蚤,具体是栉头蚤属,猫栉头蚤和犬栉头蚤,鼠蚤(印鼠客蚤)和人蚤(人蚤)。
本发明方法和组合物功效非常高,这意味着不仅在处理动物后瞬间功效很高,而且功效非常持久。
本发明的目的是一种长期防治小哺乳动物,特别是狗和猫蚤的方法,其特征在于至少一种属于化学式(I)的化合物(A)和至少一种IGR类型(昆虫生长调节剂)化合物(B),在动物可接受的和适用于局部皮肤涂敷的液体赋形剂中以杀寄生虫剂有效剂量和比例,涂敷局部皮肤,优选地限于小块皮肤面积治疗动物,该化学式(I)如下式中:
R1是CN或甲基或一个卤素原子;
R2是S(O)nR3或4,5-二氰基咪唑-2-基或卤代烷基;
R3是烷基或卤代烷基;
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7、C(O)R7、C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、烷氧基羰基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子或卤素原子,或可能CN或NO2;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基时,或者R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N;或者R2是4,5-二氰基咪唑-2-基,R4是Cl,R11是Cl,R13是CF3和X是=C-Cl。
优选地,在化学式(I)中:
R1是CN或甲基
R2是S(O)nR3
R3是烷基或卤代烷基
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7,C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子或卤素原子;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基,而R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N。
特别应该提到其中R7是CN的式(I)化合物。还应提到式中R2是S(O)nR3,优选地n=1,R3优选地是CF3或烷基(例如甲基或乙基),或者n=0,R3优选地是CF3的化合物,以及其中X=C-R12,R12是卤素原子的化合物。同样优选的是其中R11是卤素原子的化合物,以及其中R13是卤代烷基,优选地是CF3的化合物。在本发明的范围内,有利的作法是使用同时具有这些特征中的两种或多种的化合物。
优选的一类式(I)化合物是由如R1是CN,R3是卤代烷基、R4是NH2、R11和R12各自是卤素原子,和/或R13是卤代烷基的化合物构成的。
在这些化合物中,R3优选地代表CF3或乙基。
式(I)化合物中定义的烷基一般地含有1-6个碳原子。R5和R6表示的二价亚烷基以及与R5和R6连接的氮原子所构成的环,一般是5、6或7元环。
本发明中特别优选的式(I)化合物是1-(2,6-Cl2-4-CF3-苯基)--3-CN-4-(SO-CF3)-5-NH2-吡唑,其通用名是fipronil。
也可以列举由下述特征与前面化合物可区分的两种化合物:
1-n=0, R3=CF3
2-n=1, R3=乙基。
在化合物(B)中,具体可以列举模拟保幼激素的化合物,具体是:
印苦楝子素 (Agridyne)
diofenolan (汽巴.嘉基)
双氧威 (汽巴.嘉基)
烯虫乙酯 (山道士)
烯虫炔酯 (山道士)
烯虫酯 (山道士)
蚊蝇醚 (住友/M)
四氢印苦栋子素 (Agridyne)
和4-氯-2-(2-氯-2-甲丙基)-5-(6-碘3-吡啶基甲氧基)吡地嗪-3(2H)酮和几丁质合成抑制剂,具体是:
定虫隆 (Ishihara Sangyo)
灭蝇胺 (汽巴.嘉基)
除虫脲 (Solvay Duphar)
fluazuron (汽巴.嘉基)
氟螨脲 (Solvay Duphar)
氟虫脲 (Cyanamid)
氟铃脲 (Dow Elanco)
lufenuron (汽巴.嘉基)
tebufenozide (罗姆哈斯)
伏虫隆 (Cyanamid)
杀虫隆 (拜尔)
这些化合物是由国际通用命名(杀虫剂手册,第10版,1994,Ed.Clive Tomlin,Grande-Bretagne)确定的。
作为几丁质合成抑制剂,还可以列举下述化合物,如1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(1,1,2,2-四氟乙氧基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
作为化合物(B)还可以列举novaluron(Isagro,意大利公司)。
优选的化合物(B)是蒙五一五、蚊蝇醚、烯虫乙酯、灭蝇胺、lufenuron和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
其他优选的化合物(B)也是novaluron。
更可取的是相随使用,优选的是同时使用这两类化合物。
更可取的是每两个月,优选地每三个月对狗和猫按照本发明进行处理。
优选地,对动物给药进行处理的剂量是,衍生物(A)为0.1-40毫克/公斤,优选地为1-20毫克/公斤,化合物(B)为0.1-40毫克/公斤,优选地为1-30毫克/公斤。
优选的剂量是,化合物(A)为5-15毫克/公斤,优选的化合物(B)为0.5-15毫克/公斤,或其他化合物(B)为10-20毫克/公斤。
在实施本发明的另外一种方式中,化合物(A)和化合物(B)的使用可随时间而不同,还可分开使用。这样,更可取的是以一定的间隔交替使用,例如两次使用间隔为一个月,第一次优选采用化合物(A)。
人们应知道,如此标明的剂量值是平均值,在实际中由于采用具有由1-N-苯基吡唑类型衍生的化合物(A)和化合物(B)确定剂量的一种配方对不同重量的动物用药,所以这些值可以在很大范围内改变。因此,真正使用的剂量往往低或高十分之一,与优选的剂量相比,可低或高可达到十分之二、三或四,如果剂量过量,动物也不会出现中毒的危险,同时保持一种理想的效果,如果剂量不足,或许时间较短。
这种方法的目的不是治疗性的,特别是涉及通过除去存在的寄生虫以及它们的残留物和排泄物而清洗动物的毛和皮肤。这样,已处理动物具有其观感与能感更佳的毛。
本发明还涉及一种用于治疗和预防具有致病后果的寄生虫的治疗方法。
根据本发明,上述方法还可以用于防治外寄生虫,特别是蜱。
本发明还涉及一种组合物,这种组合物具体用于防治小哺乳动物身上的蚤,其特征在于该组合物含有至少一种如前面定义的式(I)化合物(A),和至少一种上述定义的化合物(B),在动物可接受的,适于局部皮肤涂敷,优选地限于小块皮肤涂敷的液体赋形剂中,具有杀寄生虫剂功效的剂量和比例。
优选地,在式(I)中:
R1是CN或甲基
R2是S(O)nR3
R3是烷基或卤代烷基
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7,C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子,或卤素原子;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基时,则R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N。
应该特别提到式中R1是CN的式(I)化合物。还应提到式中R2是S(O)nR3,优选地n=1,R3优选地是CF3或烷基(例如甲基或乙基),或者n=0,R3优选地是CF3的化合物,以及其中X=C-R12,R12是卤素原子的化合物。同样优选其中R11是卤素原子的化合物,以及其中R13是卤代烷基,优选地是CF3的化合物。在本发明的范围内,有利的作法是采用具有这些特征中的两种或多种的化合物。
优选的一类式(I)化合物是由如R1是CN,R3是卤代烷基、R4是NH2、R11和R12各自是卤素原子,和/或R13是卤代烷基的化合物构成的。
在这些化合物中,R3优选地代表CF3或乙基。
本发明中特别优选的式(I)化合物是1-(2,6-Cl2-4-CF3-苯基)-3-CN-4-(SO-CF3)-5-NH2-吡唑。
也可以列举由下述特征与前面化合物可区分的两种化合物:
1-n=0, R3=CF3
2-N=1, R3=乙基。
可以根据专利申请WO-A-87/3781、93/6089、94/21606或EP-A-0295117中所描述的方法或者根据化学合成专业技术人员熟悉知的任何其他方法制备式(I)化合物。为了化学制备本发明的产品,本领域专业人员被视作已经获取了“化学文摘”中的所有内容和其中提到的文献。
在上面大量IGR类型化合物中,更可取的是烯虫酯、蚊蝇醚、烯虫乙酯、灭蝇胺、lufenuron和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(三氟甲基)苯基脲。
novaluron也是优选的。
式(I)化合物和化合物(B)的重量比优选地为80/20至20/80。
该液体赋形剂可以是单一的或复合的,这种赋形剂适合于所选择的用药方法和方式。
这些点状涂敷组合物有利地可以包括:
b)结晶抑制剂,具体地其量为1-20%(P/V),优选地为5-15%,这种抑制剂满足下述试验:将在下面c)定义的溶剂中含有10%(P/V)式(I)化合物的0.3毫升溶液A以及10%这种抑制剂加到20℃玻璃片上达24小时,此后用裸眼观察在玻璃片上几乎没有或完全没有晶体,具体地只有不到10个晶体,优选地0个晶体,
c)介电常数为10-35,优选地为20-30的有机溶剂,在整个组合物中这种溶剂c)的含量优选地是补足100%该组合物,
d)沸点低于100℃,优选地低于80℃,介电常数为10-40,优选地为20-30的有机共溶剂;有利地,这种共溶剂在这种组合物中可以是d)/c)重量/重量(P/P)比为1/15至1/2。这种溶剂是挥发性的,为的是主要用作干燥的促进剂,这种溶剂与水和/或溶剂c)混溶。
这种点状涂敷的组合物或许可以含有具体为0-30%(以体积计,V/V),优选地为0-5%水,不过,这并非优选。
这种点状涂敷的组合物还可以含有一种用于抑制空气氧化作用的抗氧化剂,这种抗氧化剂含量具体为0.05-1%(P/V),优选地为0.01-0.05%。
用于具体地说为狗和猫的与人结伴的动物的本发明组合物,一般是涂在皮肤上;一般地涉及涂敷限于小于10厘米2的表面区域,特别是为5-10厘米2,特别是两个点,优选地限于动物两肩之间部位。涂敷后,这种组合物扩散,尤其是在整个动物身体上扩散,然后干燥,既不结晶也不改变形态(没有任何微白沉积或粉尘样子),还不触及毛。
这些本发明的点状涂敷组合物在其效果、作用快速以及在涂敷和干燥后动物毛色令人惬意程度方面都是特别有利的。
作为本发明可使用的有机溶剂c),具体可列举:
丙酮、乙腈、苯甲醇、丁基二乙二醇、二甲基乙酰胺、二甲基甲酰胺、二丙二醇正丁醚、乙醇、异丙醇、甲醇、乙二醇单乙醚、乙二醇单甲醚、单甲基乙酰胺、二丙二醇单甲醚、液体聚氧化乙二醇、丙二醇、2-吡咯烷酮,具体是N-甲基吡咯烷酮、二乙二醇单乙醚、乙二醇、邻苯二甲酸二乙酯,或其中至少两种的混合物。
作为本发明中可使用的b)结晶抑制剂,可具体列举:
-聚乙烯基吡咯烷酮、聚乙烯醇、乙酸乙烯酯与乙烯基吡咯烷酮的共聚物、聚乙二醇、苯甲醇、甘露糖醇、甘油、山梨糖醇、聚氧化亚乙基化脱水山梨糖醇酯;卵磷酯、羧甲基纤维素钠、丙烯酸衍生物,如甲基丙烯酸酯等,
-阴离子表面活性剂,如碱金属硬脂酸盐,具体为钠、钾或铵盐;硬脂酸钙;三乙醇胺的硬脂酸盐、枞酸钠;烷基硫酸盐,具体是月桂基硫酸钠和鲸蜡基硫酸钠;十二烷基苯磺酸钠、二辛基硫代琥珀酸钠;脂肪酸,具体如由椰子油衍生的化合物,
-阳离子表面活性剂,如式N+R’R”R’”R””,Y-所示的水溶性季铵盐,式中R基是烃基,或许羟基化的烃基,Y-是一种强酸的阴离子,如卤化物阴离子、硫酸根和磺酸根;鲸蜡基三甲铵溴化物成为可使用的阳离子表面活性剂的部分,
-式N+R′R″R所示的铵盐,其中R为可能被羟基化的烃基;十八烷基胺的盐酸盐中构成了适用的阳离子表面活性剂的组成部分,
-非离子表面活性剂,如山梨糖醇酯,或许聚氧化亚乙基化脱水山梨糖醇酯,具体是多乙氧基醚、聚氧化亚乙基化烷基醚;聚乙二醇硬脂酸酯、蓖麻油的聚氧化亚乙基化衍生物、聚甘油酯、聚氧化亚乙基化脂肪醇、聚氧化亚乙基化脂肪酸、环氧乙烷和环氧丙烷共聚物,
-两性表面活性剂,如甜菜碱的月桂基取代化合物,
或优选地至少两种上述化合物的混合物。
特别优选地,使用一对结晶抑制剂,即一种聚合物类型的成膜剂与一种表面活性剂的结合。这些试剂具体选自如结晶抑制剂b)所列出的化合物。
在特别优选的聚合物类型的成膜剂中,可以列举:
-不同品级的聚乙烯基吡咯烷酮,
-聚乙烯醇,
-乙酸乙烯酯和乙烯基吡咯烷酮的共聚物。
对于表面活性剂,尤其可以列举非离子表面活性剂,优选地,聚氧化亚乙基化脱水山梨糖醇酯,和具体地不同级的多山梨醇酯,例如多乙氧基醚。
另外,在所提到的结晶抑制剂总量范围内,尤其能够以接近或相同的量加入成膜剂和表面活性剂。
尽管活性物质的浓度较高,这样组成的一对还可显著地保证达到在毛上没有结晶的目的,同时保持动物毛的化妆结果,即无粘结趋势或粘性形态。
作为共溶剂d),可以具体列举:无水乙醇、异丙醇、甲醇。
作为抗氧化剂,可以具体使用通常的抗氧化剂,如:丁基羟基茴香醚、丁基羟基甲苯、抗坏血酸、偏亚硫酸氢钠、棓酸丙酯、硫代硫酸钠、至多两种上述化合物的混合物。
通常地可将如前面所定义的那些成分经简单混合制备本发明点状涂敷组合物;有利地,首先将活性物质混合到主要溶剂中,再添加其他的组分或添加剂。
根据动物的重量,猫的涂敷体积可以是约0.3-1毫升,优选地为约0.5毫升,狗的涂敷体积约为0.3-3毫升。
特别优选地,为了在动物一小块皮肤上,一般在两肩之间进行点状涂敷(点滴类型的溶液),本发明的组合物可以呈溶液、悬浮液或浓乳化液形式。不太优选地,可以考虑喷雾到动物体上的溶液或悬浮液形式、注入或撒到动物体上的溶液、悬浮液或乳化液(淋注类型溶液)形式、油、奶、软膏形式或任何其他局部用药的流体配方形式。
有利地,准备使用的这种组合物含有式(I)化合物0.1-40毫克/公斤,化合物(B)0.1-40毫克/公斤。
优选地,一种准备使用的已定量的配方,具体是点状涂敷的配方(点滴),含有1-20毫克/公斤,优选地为2-10毫克/公斤化合物(A),具体是fipronil,和1-30毫克/公斤,优选地2-10毫克/公斤优选化合物(B)或10-20毫克/公斤其他化合物(B)。
有利地,可以考虑这些准备使用的组合物按照剂量分别用于1-10、10-20、20-40公斤的动物。
在随时间推移而分开应用的其他实施方式中,可以制造一种组件形式的组合物(盒),分别将一种含有式(I)化合物的组合物,具体是fipronil,和一种含有化合物(B),优选为蚊蝇醚的组合物分开装在同一个包装盒中,每一种组合物包括一种能够涂皮肤的赋形剂。
优选地,这两种组合物中每一种都可用于局部点状(点滴)涂敷,优选地,一种容器正好装有每次涂敷使用所必需的剂量。
于是,例如在一个包装盒中,所述的组件可以装有三个各装有不同剂量的化合物(A)组合物的容器和各装有不同剂量的化合物(B)组合物的三个容器,这些容器(A)与容器(B)用标记、形状或颜色加以区分,以及一份专门的说明,说明容器(A)与容器(B)应该以一定的间隔,例如一个月交替使用,和例如由容器(A)开始使用。
本发明的这些组合物,特别是点状涂敷,在非常长时间内处理哺乳动物,特别是如狗和猫之类的小哺乳动物的蚤,显示出极好的效果。
发现化合物(A),如fipronil,溶解于包括所有动物的皮脂中,并且浓缩在皮脂腺中,由此在非常长的时间里逐渐地被盐析,这是这些组合物之所以具有这种持久效果的一种可以接受的解释,还能够解释与之组合的化合物(B)的持久作用。
这些组合物还具有防治其他寄生虫,特别是蜱的某些效果,包括可以将本发明的组合物扩展应用到处理外寄生虫,甚至处理内寄生虫时,根据兽医技术标准,这种组合物显示出一种能够实际达到的真正的效用。
于是,例如也可以使用一种以fipronil和fluazuron为主要成分的组合物治蜱。
如果必要的话,本发明的组合物还可以含有其他的杀虫剂,特别是imidaclopride。
本发明的另一目的是使用至少一种式(I)化合物(A)和至少一种如前面所定义的IGR类型化合物(B),以便制备一种如前面定义的组合物。
本发明的其他优点和特征体现在下面作为非限制性实施例的说明中。
下面的组合物制备实施例包括作为式(I)化合物(A)命名为fipronil的化合物。
作为制备一种本发明涂敷局部皮肤的组合物的实施例,有利地,可以将下列组分混合:
a1-化合物(B),1-20%(每份体积的重量百分数P/V),
a2-式(I)化合物(A),1-20%,优选地为5-15%(每份体积的重量百分数P/V),
作为实施例,本发明组合物在一种液体介质中含有下述浓度(P/V)化合物(A)和(B),其介质含有组分b、c和d中的一种组分。总体积是1毫升。
实施例1
fipronil 10%
蚊蝇醚 5%
实施例2
fipronil 5%
蚊蝇醚 5%
实施例3
fipronil 5%
蚊蝇醚 20%
实施例4
fipronil 10%
烯虫酯 30%
实施例5
fipronil 10%
1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲5%。
每支猫感染100个蚤,然后每10天再进行感染。与第一次出现症状的同时,以0.1毫升/公斤实施例1的组合物局部涂敷这些猫的皮肤。处理后两个月和最后一次感染后十天没有检测出任何蚤,所收集的卵也不是活的。
采用实施例1和2的组合物根据同样的方案处理狗,结果表明,在涂该组合物后两个月具有同样的功效。
Claims (34)
1、用于长期对小哺乳动物,特别是狗和猫提供保护作用以免受到蚤侵扰的组合物,其特征在于在一种动物可接受的,适于局部皮肤涂敷的流体赋形剂中,该组合物含有至少一种属于式(I)的化合物(A),和至少一种昆虫生长调节剂类型杀卵化合物(B):式中:
R1是CN或甲基或一个卤素原子;
R2是S(O)nR3或4,5-二氰基咪唑-2-基或卤代烷基;
R3是烷基或卤代基;
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7、C(O)R7或C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、烷氧基羰基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子,或卤素原子,或可能CN或NO2;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基,或者R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N;或者R2是4,5-二氰基咪唑-2-基,R4是Cl,R11是Cl,R13是CF3和X是=C-Cl。
2、根据权利要求1所述的组合物,其特征在于在式(I)化合物中:
R1是CN或甲基
R2是S(O)nR3
R3是烷基或卤代烷基
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7,C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、S(O)r-CF3;或R5和R6可以-起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子,或卤素原子;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基,则R3是卤代烷基,R4是NH2,R21是Cl,R13是CF3和X是N。
3、根据权利要求1或2所述的组合物,其特征在于式(I)的化合物是其中R1为CN的化合物。
4、根据权利要求1-3中任一项的组合物,其特征在于式(I)的化合物是其中R13为卤代烷基,优选地为CF3的化合物。
5、根据权利要求1-4中任一项的组合物,其特征在于式(I)的化合物是其中R2为S(O)nR3,优选地n=1,R3优选地是CF3或烷基,具体是甲基或乙基,或者n=0,R3优选地是CF3的化合物。
6、根据权利要求1-5中任一项的组合物,其特征在于式(I)的化合物是X=C-R12,R12是卤素原子的化合物。
7、根据权利要求1-6中任一项的组合物,其特征在于式(I)的化合物是R1为CN,R3是卤代烷基、R4是NH2、R11和R12各自是卤素原子,和/或R13是卤代烷基的化合物。
8、根据权利要求1-7中任一项的组合物,其中式(I)的化合物是1-(2,6-Cl2-4-CF3-苯基)-3-CN-4-(SO-CF3)-5-NH2-吡唑。
9、根据权利要求1-7中任一项的组合物,其中式(I)的化合物是下述一种化合物:
1-(2,6-Cl2-4-CF3-苯基)--3-CN-4-(SO-CF3)-5-NH2-吡唑,
1-(2,6-Cl2-4-CF3-苯基)--3-CN-4-(SO-C2H5)-5-NH2-吡唑。
10、根据权利要求1-9中任一项的组合物,其特征在于化合物(B)是模拟保幼激素的化合物,具体是:
印苦楝子素
diofenolan
双氧威
烯虫乙酯
烯虫炔酯
烯虫酯
蚊蝇醚
四氢印苦楝子素
和4-氯-2-(2-氯-2-甲丙基)-5-(6-碘-3-吡啶基甲氧基)吡地嗪-3(2H)酮,或几丁质合成抑制剂,具体是:
定虫隆
灭蝇胺
除虫脲
fluazuron
氟螨脲
氟虫脲
氟铃脲
lufenuron
tebufenozide
伏虫隆
杀虫隆
1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(1,1,2,2-四氟乙氧基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
11、根据权利要求1-9中任一项的组合物,其特征在于化合物(B)是novaluron。
12、根据权利要求10所述的组合物,其特征在于IGR型化合物选自烯虫酯、蚊蝇醚、烯虫乙酯、灭蝇胺、lufenuron和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
13、根据权利要求1-12中任一项的组合物,其特征在于式(I)化合物(A)与(B)类型化合物的重量比为80/20至20/80。
14、根据权利要求1-13中任一项的组合物,其特征在于流体赋形剂和化合物(A)和(B)的浓度都适于“点滴”类型点状皮肤涂敷。
15、根据权利要求1-14中任一项的组合物,其特征在于流体赋形剂和化合物(A)和(B)的浓度都适于“淋注”类型局部皮肤涂敷。
16、根据权利要求1-15中任一项的组合物,其特征在于流体赋形剂和化合物(A)和(B)的浓度适于涂敷限于小于10厘米2的表面区域,特别是为5-10厘米2,尤其是两个点,优选地限于动物的两肩之间。
17、根据权利要求1-16中任一项的组合物,其特征在于该组合物的剂量为0.1-40毫克/公斤化合物(A)和0.1-40毫克/公斤化合物(B)。
18、根据权利要求17所述的组合物,其特征在于该组合物的剂量为1-20毫克/公斤,优选地为2-10毫克/公斤化合物(A)和1-30毫克/公斤,优选地为2-20毫克/公斤化合物(B)。
19、根据权利要求1-18中任一项的组合物,其特征在于该组合物还含有一种结晶抑制剂(b),具体地其量为1-20%(P/V),优选地为5-15%。
20.根据权利要求19所述的组合物,其特征在于结晶抑制剂(b)选自:
-聚乙烯基吡咯烷酮、聚乙烯醇、乙酸乙烯酯与乙烯基吡咯烷酮的共聚物、聚乙二醇、苯甲醇、甘露糖醇、甘油、山梨糖醇、聚氧化亚乙基化脱水山梨糖醇酯;卵磷酯、羧甲基纤维素钠、丙烯酸衍生物,如甲基丙烯酸酯等,
-阴离子表面活性剂,如碱金属硬脂酸盐,具体为钠、钾或铵盐;硬脂酸钙;三乙醇胺的硬脂酸盐、枞酸钠;烷基硫酸盐,具体是月桂基硫酸钠和鲸蜡基硫酸钠;十二烷基苯磺酸钠、二辛基硫代琥珀酸钠;脂肪酸,具体如由椰子油衍生的化合物,
-阳离子表面活性剂,如式N+R’R”R’”R””,Y-所示的水溶性季铵盐,式中R基是烃基,或许羟基化的烃基,Y-是一种强酸的阴离子,如卤化物阴离子、硫酸根和磺酸根;鲸蜡基三甲铵溴化物成为可使用的阳离子表面活性剂的部分,
-式N+R′R″R所示的铵盐,其中R为可能被羟基化的烃基;十八烷基胺的盐酸盐构成了适用的阳离子表面活性剂的组成部分,
-非离子表面活性剂,如山梨糖醇酯,或许聚氧化亚乙基化脱水山梨糖醇酯,具体是多乙氧基醚、聚氧化亚乙基化烷基醚;聚乙二醇硬脂酸酯、蓖麻油的聚氧化亚乙基化衍生物、聚甘油酯、聚氧化亚乙基化脂肪醇、聚氧化亚乙基化脂肪酸、环氧乙烷和环氧丙烷共聚物,
-两性表面活性剂,如甜菜碱的月桂基取代化合物,
或优选地至少两种上述化合物的混合物。
21、根据权利要求19和20中任一项的组合物,其特征在于该组合物含有一对由一种聚合物类型的成膜剂与一种表面活性剂构成的结晶抑制剂,在结晶抑制剂总量范围内,其成膜剂与表面活性剂的量接近或相同。
22、根据权利要求21所述的组合物,其特征在于成膜剂选自:
-不同品级的聚乙烯基吡咯烷酮,
-聚乙烯醇,
-乙酸乙烯酯和乙烯基吡咯烷酮的共聚物。
其特征还在于表面活性剂选自非离子表面活性剂,优选地,聚氧化亚乙基化脱水山梨糖醇酯,和特别是不同品级的多山梨醇酯。
23、根据权利要求1-22中任一项的组合物,其特征在于该组合物含有介电常数为10-35,优选地为20-30的有机溶剂(c),在整个组合物中这种溶剂(c)的含量优选地是补足100%该组合物。
24、根据权利要求23的组合物,其特征在于有机溶剂(c)选自丙酮、乙腈、苯甲醇、丁基二乙二醇、二甲基乙酰胺、二甲基甲酰胺、二丙二醇正丁醚、乙醇、异丙醇、甲醇、乙二醇单乙醚、乙二醇单甲醚、单甲基乙酰胺、二丙二醇单甲醚、液体聚氧化乙二醇、丙二醇、2-吡咯烷酮,具体是N-甲基吡咯烷酮、二乙二醇单乙醚、乙二醇、邻苯二甲酸二乙酯,或至少两种上述物质的混合物。
25、根据权利要求23和24中任一项的组合物,其特征在于该组合物还含有沸点低于100℃,优选地低于80℃、介电常数为10-40,优选地为20-30、与水和/或溶剂(c)混溶的有机共溶剂(d);这种共溶剂(d)/溶剂(c)的重量/重量(P/P)比为1/15至1/2。
26、根据权利要求25的组合物,其特征在于该共溶剂(d)选自无水乙醇、异丙醇和甲醇。
27、根据权利要求1-26中任一项的组合物,其特征在于将该组合物制成组件形式,在一个包装盒中,有至少一个装有一种化合物(A)的容器,和至少一个装有化合物(B)的容器,以及一份专门的说明,说明这些容器应该以一定的间隔,具体是一个月交替使用。
28、根据权利要求1-27中任一项的组合物,其特征在于该组合物的保护作用可持续2-3月。
29、至少一种式(I)化合物(A)和至少一种昆虫生长调节剂IGR类型杀卵化合物(B)制备一种用于涂敷局部皮肤,长期对小哺乳动物,特别是狗和猫提供保护作用以免受到蚤侵扰的组合物方面的应用,其化学式(I)如下:式中:
R1是CN或甲基或一个卤素原子;
R2是S(O)nR3或4,5-二氰基咪唑-2-基或卤代烷基;
R3是烷基或卤代烷基;
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7、C(O)R7或C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、烷氧基羰基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子或卤素原子,或可能CN或NO2;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基时,或者R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N;或者R2是4,5-二氰基咪唑-2-基,R4是Cl,R11是Cl,R13是CF3和X是=C-Cl。
30、根据权利要求29所述的于制备权利要求1-28中任一项的组合物方面的用途。
31、权利要求1-28所述的组合物于防治外寄生虫,具体是蜱方面的用途。
32、长期防治小哺乳动物,特别是狗和猫的蚤的方法,其特征在于以权利要求1-28中任一项的组合物的有效杀寄生虫的剂量和比例,采用局部皮肤涂敷方法处理动物。
33、根据权利要求32所述的方法,其特征在于采用“点滴”类型的点状局部皮肤涂敷处理动物。
34、根据权利要求32和33中任一项的方法用于防治外寄生虫,特别是蜱。
Applications Claiming Priority (4)
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 |
FR96/04208 | 1996-03-29 | ||
US69211396A | 1996-08-05 | 1996-08-05 | |
US08/692,113 | 1996-08-05 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200810174967A Division CN101653122A (zh) | 1996-03-29 | 1997-03-26 | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 |
CN200910261985A Division CN101732309A (zh) | 1996-03-29 | 1997-03-26 | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1185716A true CN1185716A (zh) | 1998-06-24 |
Family
ID=26232631
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910261985A Pending CN101732309A (zh) | 1996-03-29 | 1997-03-26 | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 |
CN97190271A Pending CN1185716A (zh) | 1996-03-29 | 1997-03-26 | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910261985A Pending CN101732309A (zh) | 1996-03-29 | 1997-03-26 | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 |
Country Status (33)
Country | Link |
---|---|
US (2) | US6096329A (zh) |
JP (2) | JP3702965B2 (zh) |
CN (2) | CN101732309A (zh) |
AR (2) | AR006522A1 (zh) |
AT (1) | AT503376B1 (zh) |
AU (1) | AU731994B2 (zh) |
BE (1) | BE1010478A5 (zh) |
BR (1) | BR9702150B1 (zh) |
CA (2) | CA2221418C (zh) |
CH (1) | CH692893A8 (zh) |
CL (1) | CL2004001187A1 (zh) |
CZ (1) | CZ296852B6 (zh) |
DE (15) | DE19782317A5 (zh) |
DK (1) | DK177397B1 (zh) |
ES (1) | ES2137889B1 (zh) |
FI (2) | FI122468B (zh) |
FR (1) | FR2746597B1 (zh) |
GB (1) | GB2317564B (zh) |
GR (1) | GR1002898B (zh) |
HU (2) | HU229890B1 (zh) |
IE (1) | IE80657B1 (zh) |
IL (1) | IL122117A (zh) |
IT (1) | IT1291701B1 (zh) |
LU (2) | LU90176B1 (zh) |
MX (1) | MX9709091A (zh) |
NL (2) | NL1005676C2 (zh) |
NO (2) | NO324414B1 (zh) |
NZ (1) | NZ329112A (zh) |
PL (2) | PL204043B1 (zh) |
SE (2) | SE523820C2 (zh) |
SK (1) | SK287125B6 (zh) |
TW (1) | TW372186B (zh) |
WO (1) | WO1997036485A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102711480A (zh) * | 2010-01-29 | 2012-10-03 | 辉瑞大药厂 | 局部抗寄生虫制剂 |
CN103583546A (zh) * | 2009-09-22 | 2014-02-19 | 军士宠物护理用品股份有限公司 | 定点杀虫剂组合物 |
CN106070220A (zh) * | 2016-05-31 | 2016-11-09 | 刘园 | 一种防治棉红蜘蛛的组合物及其制备方法 |
CN107105670A (zh) * | 2014-12-31 | 2017-08-29 | 美国陶氏益农公司 | 微胶囊化的硝化抑制剂组合物 |
CN109985090A (zh) * | 2017-12-29 | 2019-07-09 | 瑞普(天津)生物药业有限公司 | 一种复方抗体外寄生虫组合物及其制备方法 |
Families Citing this family (119)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL116147A (en) * | 1994-11-30 | 2002-05-23 | Aventis Cropscience Sa | Complexible composition for insect control |
FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
US6828275B2 (en) * | 1998-06-23 | 2004-12-07 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
IE80657B1 (en) | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
TW524667B (en) * | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
AU6826898A (en) * | 1997-03-11 | 1998-09-29 | Rhone-Poulenc Agro | Pesticidal combination |
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 |
US6057355A (en) * | 1997-08-05 | 2000-05-02 | Rhone-Poulenc Inc. | Pesticidal combination |
IL124128A (en) * | 1998-03-02 | 2003-09-17 | Yair Ben Ziony | Composition comprising a benzoylphenylurea for treatment of topical fungal infection |
EP0963695A1 (en) * | 1998-06-08 | 1999-12-15 | Rhone Poulenc Agro | Insecticidal method |
EG22187A (en) * | 1999-04-15 | 2002-10-31 | Aventis Cropscience Sa | New composition |
GB9912560D0 (en) * | 1999-05-28 | 1999-07-28 | Bob Martin Company The | Ectoparasite control composition |
US6313157B1 (en) * | 1999-06-04 | 2001-11-06 | Rhone-Poulenc Agro | Insecticidal method |
AUPQ441699A0 (en) | 1999-12-02 | 2000-01-06 | Eli Lilly And Company | Pour-on formulations |
US7166294B2 (en) * | 2000-06-16 | 2007-01-23 | Centers For Disease Control And Prevention | Control of arthropods in rodents |
US20030056734A1 (en) * | 2000-06-16 | 2003-03-27 | Centers For Disease Control And Prevention | Apparatus for applying chemicals to rodents |
DE10063865A1 (de) * | 2000-12-21 | 2002-06-27 | Bayer Ag | Verwendung von Pyrazoloximen als Parasitizide |
DK2347654T3 (en) | 2001-09-17 | 2019-04-23 | Elanco Us Inc | Formulation for the control of lice or ticks in cattle |
JP2003095813A (ja) * | 2001-09-25 | 2003-04-03 | Sumika Life Tech Co Ltd | 動物の外部寄生虫駆除用液剤 |
US7132448B2 (en) | 2002-09-12 | 2006-11-07 | The Hartz Mountain Corporation | High concentration topical insecticide containing insect growth regulator |
US20050245582A1 (en) * | 2002-09-12 | 2005-11-03 | The Hartz Mountain Corporation | High concentration topical insecticides containing pyrethroids |
US7368435B2 (en) * | 2002-09-12 | 2008-05-06 | Summit Vetpharm, Llc | Topical endoparasiticide and ectoparasiticide formulations |
US7345092B2 (en) * | 2002-09-12 | 2008-03-18 | Summit Vetpharm, Llc | High concentration topical insecticides containing pyrethroids |
US6889632B2 (en) * | 2002-09-12 | 2005-05-10 | The Hartz Mountain Corporation | High concentration dinotefuran formulations containing methoprene |
US7354595B2 (en) * | 2002-09-12 | 2008-04-08 | Summit Vetpharm, Llc | High concentration dinotefuran formulations |
US20040077703A1 (en) * | 2002-10-02 | 2004-04-22 | Soll Mark D. | Nodulisporic acid derivative spot-on formulations for combating parasites |
US7262214B2 (en) | 2003-02-26 | 2007-08-28 | Merial Limited | 1-N-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases |
US6991801B2 (en) | 2003-04-04 | 2006-01-31 | Merial Limited | Topical anthelmintic veterinary formulations |
WO2005015995A1 (en) * | 2003-08-08 | 2005-02-24 | The Hartz Mountain Corporation | High concentration topical insecticides containing pyrethroids |
US7531186B2 (en) | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
US7514464B2 (en) * | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
GB0329314D0 (en) | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
US7671034B2 (en) | 2003-12-19 | 2010-03-02 | Merial Limited | Stabilized formulation of ivermectin feed premix with an extended shelf life |
SI1711058T1 (sl) * | 2004-01-23 | 2022-02-28 | Eden Research Plc, | Postopki za uničevanje nematod, ki obsega uporabo terpenske komponente |
DK1753529T3 (da) | 2004-05-20 | 2013-11-11 | Eden Research Plc | Komposition indeholdende en hul glucan-partikel eller en hul cellevægspartikel, der indkapsler en terpenkomponent, fremgangsmåder til fremstilling og anvendelse af disse |
US20060046988A1 (en) | 2004-08-30 | 2006-03-02 | Albert Boeckh | Methoprene formulations for the control of tick infestations |
US20060057173A1 (en) * | 2004-09-13 | 2006-03-16 | Whitmire Micro-Gen Research Laboratories, Inc. | Insecticide compositions and process |
IL165021A0 (en) * | 2004-11-04 | 2005-12-18 | Makhteshim Chem Works Ltd | Pesticidal composition |
UY28617A1 (es) * | 2004-11-12 | 2006-06-30 | Popley Pharma Ltda | Nuevas composiciones |
US7238365B1 (en) * | 2005-02-08 | 2007-07-03 | Wellmark International | Pesticide formulation |
US8672990B2 (en) * | 2005-05-27 | 2014-03-18 | Boston Scientific Scimed, Inc. | Fiber mesh controlled expansion balloon catheter |
EP1954130B1 (en) | 2005-11-30 | 2018-06-13 | Eden Research Plc | Methods comprising terpene mixtures comprising thymol and citral |
BRPI0619219B8 (pt) | 2005-11-30 | 2021-11-16 | Cornell Univ | Método para matar ácaros, método para tratar ou impedir a infestação por um ácaro em uma planta e uso de uma composição |
AU2012203942B2 (en) * | 2006-07-05 | 2014-11-27 | Boehringer Ingelheim Animal Health USA Inc. | 1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof |
KR101437704B1 (ko) * | 2006-07-05 | 2014-09-04 | 아벤티스 애그리컬쳐 | 1-아릴-5-알킬 피라졸 유도체 화합물, 이의 제조 방법 및 이의 사용 방법 |
US7780972B2 (en) * | 2006-07-07 | 2010-08-24 | Ididit, Inc. | Pet collar with replaceable insecticide element |
US20080038304A1 (en) * | 2006-08-14 | 2008-02-14 | Sergeant's Pet Care Products Inc. | Microencapsulated compositions for topically treating an animal against parasite infestation |
PL2066179T3 (pl) | 2006-09-01 | 2017-02-28 | E. I. Du Pont De Nemours And Company | Formulacje zawierające indoksakarb do miejscowego podawania na skórę |
KR101472602B1 (ko) * | 2006-11-10 | 2014-12-15 | 바스프 에스이 | 피프로닐의 결정질 변형물 |
US8188136B2 (en) | 2006-11-10 | 2012-05-29 | Basf Se | Crystalline modification of fipronil |
NZ552096A (en) * | 2006-12-15 | 2009-06-26 | Merial Ltd | Veterinary formulation |
DE102006061537A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
TW200846029A (en) * | 2007-02-09 | 2008-12-01 | Wyeth Corp | High dose, long-acting ectoparasiticide for extended control |
CA2628493C (en) * | 2007-04-05 | 2011-06-07 | The Hartz Mountain Corporation | Pesticidal collar with integra ted cover |
RS54332B9 (sr) | 2007-05-15 | 2019-10-31 | Merial Inc | Ariloazol-2-il cijanoetilamino jedinjenja, postupci dobijanja i postupci njihove primene |
EP2187740B1 (en) | 2007-09-06 | 2015-11-04 | The Hartz Mountain Corporation | Animal parasite-control method using insect growth regulators |
CN101854928A (zh) * | 2007-11-08 | 2010-10-06 | 希普洛有限公司 | 包含燕麦蒽酰胺的组合物 |
US20100041712A1 (en) * | 2008-08-18 | 2010-02-18 | Pfizer Inc. | Substituted imidazole combinations |
GB2464449B (en) * | 2008-09-05 | 2011-10-12 | Norbrook Lab Ltd | A topical ectoparasticide composition |
EP2364301B1 (en) | 2008-11-14 | 2015-09-02 | Merial Limited | Enantiomerically enriched aryloazol-2-yl cyanoethylamino paraciticidal compounds |
SG171751A1 (en) | 2008-11-19 | 2011-07-28 | Merial Ltd | Compositions comprising an aryl pyrazole and/ or a formamidine methods and uses thereof |
US9173728B2 (en) | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
JP5595412B2 (ja) | 2008-12-04 | 2014-09-24 | メリアル リミテッド | 二量体アベルメクチン及びミルベマイシン誘導体 |
MX2011006521A (es) | 2008-12-31 | 2011-07-12 | Makhteshim Chem Works Ltd | Metodo para controlar insectos en plantas. |
WO2010106325A2 (en) | 2009-03-18 | 2010-09-23 | Omnipharm Limited | Parasiticidal formulation |
GB0905365D0 (en) * | 2009-03-27 | 2009-05-13 | Norbrook Lab Ltd | A topical parasiticide composition |
NZ597929A (en) | 2009-07-30 | 2013-09-27 | Merial Ltd | Insecticidal 4-amino-thieno[2,3-d]-pyrimidine compounds and methods of their use |
US8614244B2 (en) | 2009-09-22 | 2013-12-24 | Segeant's Pet Care Products, Inc. | Spot-on pesticide composition |
USRE45894E1 (en) | 2009-09-22 | 2016-02-23 | Sergeant's Pet Care Products, Inc. | Spot-on pesticide composition |
MX2012006366A (es) | 2009-12-04 | 2012-06-27 | Basf Se | Compuesto de bis-organoazufre plaguicidas. |
BR112012014933B1 (pt) | 2009-12-17 | 2020-10-27 | Merial, Inc. | composições que compreendem compostos lactonas macrocíclicas e spirodioxepinoindóis |
ME03475B (me) | 2009-12-17 | 2020-01-20 | Merial Inc | Antiparazitske kompozicije dihidroazola |
UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
DK2640728T3 (en) | 2010-11-16 | 2016-11-28 | Merial Inc | NEW MONENSINDERIVATER FOR TREATMENT AND PREVENTION OF protozoal INFECTIONS |
WO2013003168A1 (en) | 2011-06-27 | 2013-01-03 | Merial Limited | Novel insect-repellent coumarin derivatives, syntheses, and methods of use |
AU2012275435B2 (en) | 2011-06-27 | 2016-07-21 | Boehringer Ingelheim Animal Health USA Inc. | Amido-pyridyl ether compounds and compositions and their use against parasites |
BR112013033914A2 (pt) | 2011-06-30 | 2016-11-22 | Hansen Ab Gmbh | agente para o controle de parasitas em animais e uso de um agente |
RS61048B1 (sr) | 2011-09-12 | 2020-12-31 | Boehringer Ingelheim Animal Health Usa Inc | Paraziticidne kompozicije koje sadrže izoksazolin aktivni agens, postupak i njihove primene |
WO2013044118A2 (en) | 2011-09-23 | 2013-03-28 | Merial Limited | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
AU2012340351B2 (en) | 2011-11-17 | 2017-06-15 | Boehringer Ingelheim Animal Health USA Inc. | Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof |
HUE036441T2 (hu) | 2011-12-02 | 2018-07-30 | Merial Inc | Hosszú hatású injektálható moxidektin készítmények és új moxidektin kristályformák |
AP2014007885A0 (en) | 2012-02-01 | 2014-08-31 | Dow Agrosciences Llc | Novel class of glyphosate resistance genes |
MY167560A (en) | 2012-02-06 | 2018-09-14 | Merial Inc | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備1-芳基-5-烷基吡唑化合物的改良方法 |
PT2895465T (pt) | 2012-04-20 | 2019-01-16 | Boehringer Ingelheim Animal Health Usa Inc | Composições parasiticidas compreendendo derivados de benzimidazoles, os seus métodos e as suas utilizações |
CN102754669B (zh) * | 2012-08-07 | 2014-03-05 | 汪甬伟 | 一种杀灭跳蚤的药物 |
NZ716598A (en) | 2012-11-20 | 2017-02-24 | Merial Inc | Anthelmintic compounds and compositions and method of using thereof |
GB201220940D0 (en) | 2012-11-21 | 2013-01-02 | Eden Research Plc | Method P |
SI2950795T1 (en) | 2013-01-31 | 2018-07-31 | Merial, Inc. | A method of treating and treating leishmaniosis using feksinidazole |
US8993613B2 (en) | 2013-04-17 | 2015-03-31 | The Hartz Mountain Corporation | Ectoparasiticidal formulations |
SG11201603430XA (en) | 2013-11-01 | 2016-05-30 | Merial Ltd | Antiparasitic and pesticidal isoxazoline compounds |
EP2875726A1 (fr) | 2013-11-13 | 2015-05-27 | Ceva Animal Health | Nouvelles applications de compositions vétérinaires dans le traitement contre les parasites |
US9107420B2 (en) | 2014-01-13 | 2015-08-18 | Eliana Ellern | Animal shampoo |
US10857121B2 (en) | 2014-04-17 | 2020-12-08 | Merial Inc. | Use of malononitrile compounds for protecting animals from parasites |
MX361606B (es) | 2014-05-19 | 2018-12-11 | Merial Inc | Compuestos antihelmínticos. |
JP6619756B2 (ja) | 2014-06-19 | 2019-12-11 | メリアル インコーポレイテッド | インドール誘導体を含む殺寄生虫性組成物、寄生虫駆除方法及びこれらの使用 |
US20170136080A1 (en) * | 2014-06-30 | 2017-05-18 | Ceva Santé Animale | Novel method for the topical application of veterinary agents |
ES2887302T3 (es) | 2014-10-31 | 2021-12-22 | Boehringer Ingelheim Animal Health Usa Inc | Composiciones parasiticidas que comprenden fipronil |
UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
US9949487B1 (en) | 2015-03-27 | 2018-04-24 | The Hartz Mountain Corporation | Ectoparasiticidal formulations and methods using combinations of insect growth regulators |
NZ737610A (en) | 2015-05-20 | 2023-07-28 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic depsipeptide compounds |
US20160347829A1 (en) | 2015-05-27 | 2016-12-01 | Merial Inc. | Compositions containing antimicrobial IgY antibodies, for treatment and prevention of disorders and diseases caused by oral health compromising (OHC) microorganisms |
EP3120846A1 (en) | 2015-07-24 | 2017-01-25 | Ceva Sante Animale | Compositions and uses thereof for controlling ectoparasites in non-human mammals |
GB201520724D0 (en) * | 2015-11-24 | 2016-01-06 | Merial Inc | Veterinary formulations |
UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
CA3040278A1 (en) | 2016-10-14 | 2018-04-19 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
CN110167921A (zh) | 2016-11-16 | 2019-08-23 | 勃林格殷格翰动物保健美国公司 | 驱蠕虫缩肽化合物 |
AU2018292285B2 (en) | 2017-06-26 | 2023-05-25 | Boehringer Ingelheim Animal Health USA Inc. | Dual active parasiticidal granule compositions, methods and uses thereof |
JP6918350B2 (ja) * | 2017-07-06 | 2021-08-11 | 株式会社大阪製薬 | 動物用害虫防除具 |
EP3668866B1 (en) | 2017-08-14 | 2023-01-18 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal pyrazole-isoxazoline compounds |
IL279977B1 (en) | 2018-07-09 | 2024-02-01 | Boehringer Ingelheim Animal Health Usa Inc | Heterocyclic anthelmintic compounds |
CN113260419A (zh) | 2018-11-20 | 2021-08-13 | 勃林格殷格翰动物保健美国公司 | 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 |
JP2022522200A (ja) | 2019-03-01 | 2022-04-14 | ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド | 注射用クロルスロン組成物、その方法および使用 |
PE20220281A1 (es) | 2019-03-19 | 2022-02-25 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de aza-benzotiofeno y aza-benzofurano como antihelminticos |
IL298596A (en) | 2020-05-29 | 2023-01-01 | Boehringer Ingelheim Animal Health Usa Inc | Heterocyclic anthelmintic compounds |
EP4262789A1 (en) | 2020-12-21 | 2023-10-25 | Boehringer Ingelheim Vetmedica GmbH | Parasiticidal collar comprising isoxazoline compounds |
WO2023156938A1 (en) | 2022-02-17 | 2023-08-24 | Boehringer Ingelheim Vetmedica Gmbh | Method and system for providing a fluid product mailer |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3355736B2 (ja) * | 1993-12-20 | 2002-12-09 | 住友化学工業株式会社 | 殺虫、殺ダニ剤組成物 |
CA1069823A (en) * | 1975-08-06 | 1980-01-15 | James A. Lowery | Solution of a oxazepine for oral or parenteral administration |
DE3029426A1 (de) * | 1980-08-02 | 1982-03-11 | Bayer Ag, 5090 Leverkusen | Gegen zwecken wirksame pour-on-formulierungen |
DE3041814A1 (de) * | 1980-11-06 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Formulierung zur bekaempfung von tierischen ektoparasiten, insbesondere insekten und acarinen |
GB8531485D0 (en) | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
DE3606476A1 (de) * | 1986-02-28 | 1987-09-03 | Bayer Ag | 1-arylpyrazole |
JPH0768205B2 (ja) * | 1986-05-13 | 1995-07-26 | 住友化学工業株式会社 | ベンゾイル尿素誘導体およびそれを有効成分とする殺虫剤 |
NZ221262A (en) * | 1986-08-06 | 1990-08-28 | Ciba Geigy Ag | Preventing the reinfestation of dogs and cats by fleas by administering to the host a flea growth inhibiting substance orally, parenterally or by implant |
AU596867B2 (en) * | 1986-09-29 | 1990-05-17 | Del Laboratories, Inc. | Pediculicidal/ovicidal shampoo composition |
IT1213420B (it) * | 1986-12-19 | 1989-12-20 | Donegani Guido Ist | "n(-2,6-difluorobenzoil)-n'-3-cloro -41,1,2-trifluoro-2-(trifluorometossi ) etossi fenil urea ad attivita'insetticida. |
IT1214292B (it) | 1987-05-05 | 1990-01-10 | Garda Impianti Srl | Apparecchiatura per la misura e/o il controllo della posizione edella orientazione di punti o zone caratteristiche di strutture, in particolare di scocche di autoveicoli. |
DE3719733A1 (de) * | 1987-06-12 | 1989-01-05 | Bayer Ag | Substituierte 5-ethylamino-1-arylpyrazole |
DE3724919A1 (de) * | 1987-07-28 | 1989-02-09 | Bayer Ag | 1-arylpyrazole |
DE3726529A1 (de) * | 1987-08-10 | 1989-02-23 | Bayer Ag | 1-arylpyrazole |
AU605652B2 (en) * | 1987-12-15 | 1991-01-17 | Sumitomo Chemical Company, Limited | Insecticidal aerosol |
GB8816915D0 (en) | 1988-07-15 | 1988-08-17 | May & Baker Ltd | New compositions of matter |
DE3825172A1 (de) * | 1988-07-23 | 1990-01-25 | Bayer Ag | Mittel zur bekaempfung von floehen |
GB8904541D0 (en) * | 1989-02-28 | 1989-04-12 | Pharmacal International Limite | Pediculicidal compositions |
US5169846A (en) * | 1989-10-12 | 1992-12-08 | Crooks Michael J | Non-aqueous micellar solutions of anthelmintic benzimidazoles, closantel, or phenothiazine, and insect growth regulators |
ES2106779T3 (es) * | 1990-04-18 | 1997-11-16 | Procter & Gamble | Composiciones para el tratamiento anti-piojos. |
DE4025345A1 (de) * | 1990-08-10 | 1992-02-13 | Bayer Ag | Verfahren und mittel zur bekaempfung von floehen |
NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
JPH04321602A (ja) * | 1991-04-17 | 1992-11-11 | Shinto Paint Co Ltd | 浄化槽に発生する害虫の防除方法 |
ATE144102T1 (de) * | 1991-05-31 | 1996-11-15 | Sandoz Ag | Methode zur bekämpfung von flöhen |
GB9120641D0 (en) | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
US5439924A (en) | 1991-12-23 | 1995-08-08 | Virbac, Inc. | Systemic control of parasites |
AU660205B2 (en) * | 1991-12-23 | 1995-06-15 | Virbac, Inc | Systemic control of parasites |
GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
JP3715994B2 (ja) * | 1993-12-21 | 2005-11-16 | 住友化学株式会社 | 害虫防除剤 |
US5612047A (en) | 1994-03-08 | 1997-03-18 | Duffy; Eric P. | Pesticidal microemulsion formulation |
DE4414333A1 (de) | 1994-04-25 | 1995-10-26 | Bayer Ag | Substituierte Pyridylpyrazole |
WO1995033380A1 (en) * | 1994-06-08 | 1995-12-14 | Ciba-Geigy Ag | Synergistic composition |
US6221894B1 (en) * | 1995-03-20 | 2001-04-24 | Merck & Co., Inc. | Nodulisporic acid derivatives |
JPH0967221A (ja) * | 1995-08-31 | 1997-03-11 | Otsuka Chem Co Ltd | 殺線虫剤組成物及び該組成物を用いる松の枯損症防止方法 |
FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
IE80657B1 (en) | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
JPH10130104A (ja) * | 1996-11-01 | 1998-05-19 | Sumitomo Chem Co Ltd | 農薬乳剤 |
IT1290845B1 (it) * | 1996-12-12 | 1998-12-14 | Isagro Spa | Composizioni per il controllo sistemico di parassiti di animali a sangue caldo |
-
1997
- 1997-03-24 IE IE970229A patent/IE80657B1/en not_active IP Right Cessation
- 1997-03-25 AR ARP970101181A patent/AR006522A1/es active IP Right Grant
- 1997-03-26 DE DE19782317T patent/DE19782317A5/de active Granted
- 1997-03-26 DE DE19782316.5A patent/DE19782316B4/de not_active Expired - Lifetime
- 1997-03-26 PL PL378707A patent/PL204043B1/pl unknown
- 1997-03-26 PL PL323604A patent/PL191984B1/pl unknown
- 1997-03-26 DE DE19782318.1A patent/DE19782318B4/de not_active Expired - Lifetime
- 1997-03-26 JP JP53497797A patent/JP3702965B2/ja not_active Expired - Lifetime
- 1997-03-26 IL IL12211797A patent/IL122117A/xx not_active IP Right Cessation
- 1997-03-26 HU HU9900713A patent/HU229890B1/hu active Protection Beyond IP Right Term
- 1997-03-26 DE DE19782324.6T patent/DE19782324B4/de not_active Expired - Lifetime
- 1997-03-26 DE DE19782314.9A patent/DE19782314B4/de not_active Expired - Lifetime
- 1997-03-26 ES ES009750027A patent/ES2137889B1/es not_active Expired - Fee Related
- 1997-03-26 CN CN200910261985A patent/CN101732309A/zh active Pending
- 1997-03-26 DE DE19780440T patent/DE19780440B3/de not_active Expired - Lifetime
- 1997-03-26 BR BRPI9702150-4A patent/BR9702150B1/pt active IP Right Grant
- 1997-03-26 CH CH02790/97A patent/CH692893A8/fr not_active IP Right Cessation
- 1997-03-26 DE DE19782314T patent/DE19782314A5/de active Granted
- 1997-03-26 WO PCT/FR1997/000541 patent/WO1997036485A1/fr active Application Filing
- 1997-03-26 DE DE19782320.3A patent/DE19782320B4/de not_active Expired - Lifetime
- 1997-03-26 CA CA002221418A patent/CA2221418C/en not_active Expired - Lifetime
- 1997-03-26 GR GR970100109A patent/GR1002898B/el not_active IP Right Cessation
- 1997-03-26 NZ NZ329112A patent/NZ329112A/xx not_active IP Right Cessation
- 1997-03-26 DE DE19782316T patent/DE19782316A5/de active Granted
- 1997-03-26 CA CA2553413A patent/CA2553413C/en not_active Expired - Lifetime
- 1997-03-26 DE DE19782317.3A patent/DE19782317B4/de not_active Expired - Lifetime
- 1997-03-26 DE DE19782315.7A patent/DE19782315B4/de not_active Expired - Lifetime
- 1997-03-26 DE DE19782321.1T patent/DE19782321A5/de active Pending
- 1997-03-26 DE DE19782321.1A patent/DE19782321B4/de not_active Expired - Lifetime
- 1997-03-26 FR FR9703711A patent/FR2746597B1/fr not_active Expired - Lifetime
- 1997-03-26 AU AU25129/97A patent/AU731994B2/en not_active Expired
- 1997-03-26 CZ CZ0368597A patent/CZ296852B6/cs not_active IP Right Cessation
- 1997-03-26 DE DE19782315T patent/DE19782315A5/de active Granted
- 1997-03-26 DE DE19782323.8T patent/DE19782323B4/de not_active Expired - Lifetime
- 1997-03-26 SK SK1601-97A patent/SK287125B6/sk not_active IP Right Cessation
- 1997-03-26 CN CN97190271A patent/CN1185716A/zh active Pending
- 1997-03-26 GB GB9725262A patent/GB2317564B/en not_active Expired - Lifetime
- 1997-03-27 BE BE9700275A patent/BE1010478A5/fr not_active IP Right Cessation
- 1997-03-27 NL NL1005676A patent/NL1005676C2/nl not_active IP Right Cessation
- 1997-03-28 IT IT97TO000268A patent/IT1291701B1/it active IP Right Grant
- 1997-04-14 TW TW086104770A patent/TW372186B/zh not_active IP Right Cessation
- 1997-05-27 US US08/863,692 patent/US6096329A/en not_active Expired - Lifetime
- 1997-11-24 SE SE9704304A patent/SE523820C2/sv not_active IP Right Cessation
- 1997-11-25 MX MX9709091A patent/MX9709091A/es unknown
- 1997-11-26 LU LU90176A patent/LU90176B1/fr active Protection Beyond IP Right Term
- 1997-11-27 FI FI974351A patent/FI122468B/fi not_active IP Right Cessation
- 1997-11-27 DK DKPA199701364A patent/DK177397B1/da not_active IP Right Cessation
- 1997-11-27 NO NO19975472A patent/NO324414B1/no not_active IP Right Cessation
-
2002
- 2002-01-17 US US10/052,597 patent/US6685954B2/en not_active Expired - Lifetime
-
2003
- 2003-09-16 SE SE0302462A patent/SE528314C2/sv not_active IP Right Cessation
-
2004
- 2004-04-22 NL NL300149C patent/NL300149I2/nl unknown
- 2004-05-20 CL CL200401187A patent/CL2004001187A1/es unknown
- 2004-08-11 LU LU91095C patent/LU91095I2/fr unknown
- 2004-11-12 JP JP2004329139A patent/JP2005132844A/ja active Pending
-
2007
- 2007-05-02 NO NO20072287A patent/NO325293B1/no unknown
- 2007-06-26 AT AT0098907A patent/AT503376B1/de not_active IP Right Cessation
-
2008
- 2008-03-18 AR ARP080101119A patent/AR066190A2/es not_active Application Discontinuation
-
2011
- 2011-02-28 FI FI20115199A patent/FI122765B/fi not_active IP Right Cessation
-
2015
- 2015-03-05 HU HUS1500010C patent/HUS1500010I1/hu unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103583546A (zh) * | 2009-09-22 | 2014-02-19 | 军士宠物护理用品股份有限公司 | 定点杀虫剂组合物 |
CN102711480A (zh) * | 2010-01-29 | 2012-10-03 | 辉瑞大药厂 | 局部抗寄生虫制剂 |
CN107105670A (zh) * | 2014-12-31 | 2017-08-29 | 美国陶氏益农公司 | 微胶囊化的硝化抑制剂组合物 |
CN106070220A (zh) * | 2016-05-31 | 2016-11-09 | 刘园 | 一种防治棉红蜘蛛的组合物及其制备方法 |
CN109985090A (zh) * | 2017-12-29 | 2019-07-09 | 瑞普(天津)生物药业有限公司 | 一种复方抗体外寄生虫组合物及其制备方法 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1185716A (zh) | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 | |
CN100337545C (zh) | 可应用于皮肤的,用于抑制动物体上寄生虫的液体制剂 | |
CN1089553C (zh) | 可经皮施用的杀寄生虫制剂 | |
CN1240280C (zh) | 增效杀虫混合物 | |
CN1165471A (zh) | 用于治疗与保护家畜的抗寄生物组合物 | |
CN1214611A (zh) | 用于控制人体寄生虫和螨虫的组合物 | |
CN1905794A (zh) | 包含1-n-芳基吡唑衍生物和甲脒的局部制剂 | |
CN88100834A (zh) | (+)1r-反式-2,2-二甲基-3-(2,2-二氯乙烯基)-环丙羧酸2,3,5,6-四氟苄基酯 | |
CN1901796A (zh) | 含有昆虫生长调节剂的高浓度局部杀虫剂 | |
CN1026548C (zh) | 植物保护组合物 | |
CN1213656C (zh) | 基于酰胺化合物和吡啶衍生物的杀真菌混合物 | |
CN1213659C (zh) | 具有季铵基的聚硅氧烷作为制剂辅助剂的用途,以及含有它们的组合物 | |
CN1303880C (zh) | 包含环己烯酮肟醚的增效除草混合物 | |
CN1107673C (zh) | 杀虫剂1-芳基-3-亚氨基吡唑 | |
FR2761232A1 (fr) | Procede et moyens d'eradication des puces dans les locaux habites par les petits mammiferes | |
CN1294812C (zh) | 抗人体寄生虫和螨虫的含水制剂 | |
CN1335131A (zh) | 一种局部给药制剂 | |
CN1939909A (zh) | 控制动物中的节肢动物 | |
CN1028345C (zh) | 杀节肢动物组合物 | |
CN1306394A (zh) | 杀外寄生虫组合物 | |
CN1308067A (zh) | 制备低游离甲醛的羟甲基乙内酰脲组合物的方法 | |
CN1225167C (zh) | 以n-苯基吡唑为主要成分的用于狗和猫的治蚤和治蜱项圈 | |
CN1225168C (zh) | 用于对动物生活环境进行抗寄生虫处理的方法 | |
CN1524420A (zh) | 一种含有甲胺基阿维菌素和拟除虫菊酯化合物的杀虫组合物 | |
CN1250441A (zh) | 农药1-芳基吡唑 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C12 | Rejection of a patent application after its publication | ||
RJ01 | Rejection of invention patent application after publication |
Open date: 19980624 |