NL1005676C2 - Samenstelling met insecticide werking tegen vlooien bij zoogdieren, in het bijzonder honden en katten. - Google Patents

Samenstelling met insecticide werking tegen vlooien bij zoogdieren, in het bijzonder honden en katten. Download PDF

Info

Publication number: NL1005676C2
Authority: NL; Netherlands
Prior art keywords: alkyl; haloalkyl; group; composition according; compound
Prior art date: 1996-03-29

Application number

NL1005676A

Other languages

English (en)

Dutch (nl)

Inventor

Philippe Jeannin

Original Assignee

Rhone Merieux

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-03-29

Filing date

1997-03-27

Publication date

1997-09-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26232631&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NL1005676(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-03-29 Priority claimed from FR9604208A external-priority patent/FR2746594B1/fr

1997-03-27 Application filed by Rhone Merieux filed Critical Rhone Merieux

1997-09-30 Application granted granted Critical

1997-09-30 Publication of NL1005676C2 publication Critical patent/NL1005676C2/nl

Links

239000000203 mixture Substances 0.000 title claims description 98
241000282472 Canis lupus familiaris Species 0.000 title claims description 14
241000282326 Felis catus Species 0.000 title claims description 12
241000124008 Mammalia Species 0.000 title claims description 11
230000000749 insecticidal effect Effects 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 110
125000001188 haloalkyl group Chemical group 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 48
125000005843 halogen group Chemical group 0.000 claims description 39
-1 4,5-dicyanimidazol-2-yl Chemical group 0.000 claims description 35
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
241001465754 Metazoa Species 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
238000002425 crystallisation Methods 0.000 claims description 12
230000008025 crystallization Effects 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
239000003112 inhibitor Substances 0.000 claims description 9
239000007788 liquid Substances 0.000 claims description 9
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
239000006184 cosolvent Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
239000004544 spot-on Substances 0.000 claims description 7
241000238876 Acari Species 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
241000238631 Hexapoda Species 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
229920001214 Polysorbate 60 Polymers 0.000 claims description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000003093 cationic surfactant Substances 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
244000078703 ectoparasite Species 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229930002897 methoprene Natural products 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 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
229910052717 sulfur Chemical group 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
239000004094 surface-active agent Substances 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
230000000699 topical effect Effects 0.000 claims description 6
229920002101 Chitin Polymers 0.000 claims description 5
239000005891 Cyromazine Substances 0.000 claims description 5
239000005912 Lufenuron Substances 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 5
229950000775 cyromazine Drugs 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
230000002401 inhibitory effect Effects 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
239000004215 Carbon black (E152) Substances 0.000 claims description 4
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229920001577 copolymer Polymers 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
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
239000003630 growth substance Substances 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
239000002736 nonionic surfactant Substances 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
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 4
229920001223 polyethylene glycol Polymers 0.000 claims description 4
229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 4
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
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 3
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 3
239000002253 acid Substances 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
150000004665 fatty acids Chemical class 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
229930191400 juvenile hormones Natural products 0.000 claims description 3
229950003442 methoprene Drugs 0.000 claims description 3
150000004180 methoprene derivatives Chemical group 0.000 claims description 3
239000003921 oil Substances 0.000 claims description 3
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 3
229920000053 polysorbate 80 Polymers 0.000 claims description 3
229940068968 polysorbate 80 Drugs 0.000 claims description 3
239000004540 pour-on Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-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
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
239000005878 Azadirachtin Substances 0.000 claims description 2
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical class [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 2
235000013162 Cocos nucifera Nutrition 0.000 claims description 2
244000060011 Cocos nucifera Species 0.000 claims description 2
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 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
229930195725 Mannitol Natural products 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
239000002202 Polyethylene glycol Substances 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
239000005937 Tebufenozide Substances 0.000 claims description 2
239000005938 Teflubenzuron Substances 0.000 claims description 2
239000005942 Triflumuron Substances 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000005215 alkyl ethers Chemical class 0.000 claims description 2
150000008051 alkyl sulfates Chemical class 0.000 claims description 2
239000002280 amphoteric surfactant Substances 0.000 claims description 2
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 2
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 2
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 2
229960003237 betaine Drugs 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
239000004359 castor oil Substances 0.000 claims description 2
235000019438 castor oil 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
APMCZEMFQVQTHY-AGACNZRVSA-N dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodecan-9-yl]-6-methyl-14-(2-methylbutanoyloxy)-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate Chemical compound C([C@@H]([C@]1(CCO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@](C)([C@@H]1O)[C@@H]2[C@@](O)(C(=O)OC)OC[C@@]32[C@H]2[C@H]1OC[C@]2(C(=O)OC)[C@H](OC(C)=O)C[C@@H]3OC(=O)C(C)CC APMCZEMFQVQTHY-AGACNZRVSA-N 0.000 claims description 2
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 2
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 claims description 2
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 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
150000002191 fatty alcohols 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
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
150000002334 glycols Chemical class 0.000 claims description 2
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
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
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 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
229940080264 sodium dodecylbenzenesulfonate Drugs 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
VCLVUNFJTOOMIR-UHFFFAOYSA-M sodium;acetyl sulfate Chemical compound [Na+].CC(=O)OS([O-])(=O)=O VCLVUNFJTOOMIR-UHFFFAOYSA-M 0.000 claims description 2
239000000600 sorbitol Substances 0.000 claims description 2
235000010356 sorbitol Nutrition 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical class [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-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
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
229920002554 vinyl polymer Polymers 0.000 claims description 2
230000007774 longterm Effects 0.000 claims 2
238000004806 packaging method and process Methods 0.000 claims 2
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QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims 1
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SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
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239000003963 antioxidant agent Substances 0.000 description 5
235000006708 antioxidants Nutrition 0.000 description 5
244000045947 parasite Species 0.000 description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000002297 parasiticide Substances 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
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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
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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 description 1
WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-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
241000258922 Ctenocephalides Species 0.000 description 1
241000258924 Ctenocephalides felis Species 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241001399426 Myas Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
241001036422 Nosopsyllus fasciatus Species 0.000 description 1
208000005374 Poisoning Diseases 0.000 description 1
241000718000 Pulex irritans Species 0.000 description 1
241001414987 Strepsiptera Species 0.000 description 1
241000353223 Xenopsylla cheopis Species 0.000 description 1
MCNRKFGICFMITE-UHFFFAOYSA-N [2-fluoro-4-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(C(F)(F)F)C=C1F MCNRKFGICFMITE-UHFFFAOYSA-N 0.000 description 1
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 description 1
239000000654 additive Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
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239000011668 ascorbic acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
210000001217 buttock Anatomy 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
239000001768 carboxy methyl cellulose Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
244000079386 endoparasite Species 0.000 description 1
RTNCLECITJFRSB-UHFFFAOYSA-N ethoxyethane 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO.C(C)OCC RTNCLECITJFRSB-UHFFFAOYSA-N 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
229940100242 glycol stearate Drugs 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
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235000010445 lecithin Nutrition 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
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239000000473 propyl gallate Substances 0.000 description 1
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235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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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
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241000894007 species Species 0.000 description 1
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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)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Environmental Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Epidemiology (AREA)
Dermatology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Birds (AREA)
Toxicology (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)

NL1005676A 1996-03-29 1997-03-27 Samenstelling met insecticide werking tegen vlooien bij zoogdieren, in het bijzonder honden en katten. NL1005676C2 (nl)

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
FR9604208		1996-03-29
US69211396A	1996-08-05	1996-08-05
US69211396		1996-08-05

Publications (1)

Publication Number	Publication Date
NL1005676C2 true NL1005676C2 (nl)	1997-09-30

Family

ID=26232631

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NL1005676A NL1005676C2 (nl)	1996-03-29	1997-03-27	Samenstelling met insecticide werking tegen vlooien bij zoogdieren, in het bijzonder honden en katten.
NL300149C NL300149I2 (nl)	1996-03-29	2004-04-22	Samenstelling met insecticide werking tegen vlooien bij zoogdieren, in het bijzonder honden en katten.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NL300149C NL300149I2 (nl)	1996-03-29	2004-04-22	Samenstelling met insecticide werking tegen vlooien bij zoogdieren, in het bijzonder honden en katten.

Country Status (33)

Country	Link
US (2)	US6096329A (el)
JP (2)	JP3702965B2 (el)
CN (2)	CN1185716A (el)
AR (2)	AR006522A1 (el)
AT (1)	AT503376B1 (el)
AU (1)	AU731994B2 (el)
BE (1)	BE1010478A5 (el)
BR (1)	BR9702150B1 (el)
CA (2)	CA2221418C (el)
CH (1)	CH692893A8 (el)
CL (1)	CL2004001187A1 (el)
CZ (1)	CZ296852B6 (el)
DE (15)	DE19782321A5 (el)
DK (1)	DK177397B1 (el)
ES (1)	ES2137889B1 (el)
FI (2)	FI122468B (el)
FR (1)	FR2746597B1 (el)
GB (1)	GB2317564B (el)
GR (1)	GR1002898B (el)
HU (2)	HU229890B1 (el)
IE (1)	IE80657B1 (el)
IL (1)	IL122117A (el)
IT (1)	IT1291701B1 (el)
LU (2)	LU90176B1 (el)
MX (1)	MX9709091A (el)
NL (2)	NL1005676C2 (el)
NO (2)	NO324414B1 (el)
NZ (1)	NZ329112A (el)
PL (2)	PL204043B1 (el)
SE (2)	SE523820C2 (el)
SK (1)	SK287125B6 (el)
TW (1)	TW372186B (el)
WO (1)	WO1997036485A1 (el)

Families Citing this family (131)

* Cited by examiner, † Cited by third party
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
WO1998039972A1 (en) *	1997-03-11	1998-09-17	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
US20030056734A1 (en) *	2000-06-16	2003-03-27	Centers For Disease Control And Prevention	Apparatus for applying chemicals to rodents
US7166294B2 (en) *	2000-06-16	2007-01-23	Centers For Disease Control And Prevention	Control of arthropods in rodents
DE10063865A1 (de) *	2000-12-21	2002-06-27	Bayer Ag	Verwendung von Pyrazoloximen als Parasitizide
CA2460692C (en)	2001-09-17	2012-12-18	Eli Lilly And Company	Pesticidal formulations
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
US6889632B2 (en) *	2002-09-12	2005-05-10	The Hartz Mountain Corporation	High concentration dinotefuran formulations containing methoprene
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- 1997-03-26 CN CN200910261985A patent/CN101732309A/zh active Pending
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Also Published As

Publication number	Publication date
CZ296852B6 (cs)	2006-07-12
DE19782324B4 (de)	2019-05-23
NO20072287L (no)	1998-01-29
AT503376A2 (de)	2007-09-15
TW372186B (en)	1999-10-21
SE0302462D0 (sv)	2003-09-16
HUP9900713A2 (hu)	1999-06-28
AR006522A1 (es)	1999-09-08
AT503376A3 (de)	2008-11-15
DE19782318B4 (de)	2016-03-03
CL2004001187A1 (es)	2005-04-08
DE19782314B4 (de)	2016-01-21
DE19780440T1 (de)	1998-05-20
DE19782316A5 (de)	2013-01-31
DE19782323A5 (de)	2016-01-28
DE19782320B4 (de)	2016-06-02
FR2746597B1 (fr)	1998-11-06
SE9704304D0 (sv)	1997-11-24
CN101732309A (zh)	2010-06-16
DE19782323B4 (de)	2019-05-23
PL191984B1 (pl)	2006-07-31
DE19782314A5 (de)	2013-01-31
CN1185716A (zh)	1998-06-24
ES2137889B1 (es)	2001-01-01
JP3702965B2 (ja)	2005-10-05
FR2746597A1 (fr)	1997-10-03
MX9709091A (es)	1998-06-30
BE1010478A5 (fr)	1998-09-01
SK160197A3 (en)	1998-10-07
DE19782315A5 (de)	2013-01-31
HU229890B1 (en)	2014-11-28
DE19782321B4 (de)	2016-04-14
CH692893A8 (fr)	2003-02-14
AU731994B2 (en)	2001-04-12
BR9702150A (pt)	1999-07-20
CA2221418A1 (fr)	1997-10-09
DK136497A (da)	1998-01-29
DE19780440B3 (de)	2013-04-18
FI974351A0 (fi)	1997-11-27
SE523820C2 (sv)	2004-05-18
US6685954B2 (en)	2004-02-03
IL122117A (en)	2000-11-21
SE9704304L (sv)	1997-11-24
SE0302462L (sv)	2003-09-16
NL300149I2 (nl)	2004-08-02
GB2317564A (en)	1998-04-01
JPH11508276A (ja)	1999-07-21
LU90176B1 (fr)	1998-01-27
GB9725262D0 (en)	1998-01-28
SE528314C2 (sv)	2006-10-17
DE19782321A5 (de)	2014-09-04
DK177397B1 (da)	2013-03-18
US6096329A (en)	2000-08-01
SK287125B6 (sk)	2009-12-07
NO975472L (no)	1998-01-29
NZ329112A (en)	1999-11-29
GR1002898B (el)	1998-05-11
CZ368597A3 (cs)	1998-08-12
PL204043B1 (pl)	2009-12-31
CA2553413A1 (en)	1997-10-09
IL122117A0 (en)	1998-04-05
FI974351L (fi)	1997-11-27
DE19782324A5 (de)	2016-04-07
DE19782317A5 (de)	2013-01-31
NO325293B1 (no)	2008-03-17
ITTO970268A1 (it)	1998-09-28
AU2512997A (en)	1997-10-22
NO324414B1 (no)	2007-10-08
US20020090387A1 (en)	2002-07-11
FI20115199L (fi)	2011-02-28
DE19782317B4 (de)	2016-03-17
WO1997036485A1 (fr)	1997-10-09
AR066190A2 (es)	2009-08-05
AT503376B1 (de)	2010-11-15
BR9702150B1 (pt)	2009-01-13
IT1291701B1 (it)	1999-01-21
CA2221418C (en)	2008-11-25
PL323604A1 (en)	1998-04-14
HUS1500010I1 (hu)	2017-05-29
FI122468B (fi)	2012-02-15
CH692893A5 (fr)	2002-12-13
DE19782316B4 (de)	2016-03-03
IE970229A1 (en)	1997-10-08
JP2005132844A (ja)	2005-05-26
NL300149I1 (nl)	2004-07-01
DE19782315B4 (de)	2016-01-28
ES2137889A1 (es)	1999-12-16
HUP9900713A3 (en)	2001-02-28
IE80657B1 (en)	1998-11-04
GB2317564B (en)	2000-11-15
FI122765B (fi)	2012-06-29
NO975472D0 (no)	1997-11-27
LU91095I2 (fr)	2004-10-11
CA2553413C (en)	2011-10-11

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Date	Code	Title	Description
1997-12-01	PD2B	A search report has been drawn up
1998-06-02	TD	Modifications of names of proprietors of patents	Owner name: MERIAL
2004-08-02	KC1	Grant of a supplementary protection certificate	Free format text: 300149, 20170327, EXPIRES: 20190126 Spc suppl protection certif: 300149 Expiry date: 20190126
2017-03-29	MK	Patent expired because of reaching the maximum lifetime of a patent	Effective date: 20170326
2018-01-24	SPCX	Supplementary protection certificate expired	Free format text: PRODUCT NAME: FIPRONIL EN METHOPREEN; NATIONAL REGISTRATION NO/DATE: REG NL 10138 20040127; FIRST REGISTRATION: FR 677845.6 20030123 Spc suppl protection certif: 300149 Filing date: 20040422 Expiry date: 20170326 Extension date: 20180122

Publication	Publication Date	Title
AU731994B2 (en)	2001-04-12	Insecticidal combination effective against fleas on mammals, particularly cats and dogs
US6010710A (en)	2000-01-04	Direct pour-on skin solution for antiparasitic use in cattle and sheep
US6716442B2 (en)	2004-04-06	Process and means for the eradication of fleas in the habitats of small mammals
US6797724B2 (en)	2004-09-28	Direct spot-on antiparasitic skin solution for domestic animals
NL1005673C2 (nl)	1997-11-18	Oplossing voor directe aanbrenging op de huid voor gebruik als anti-parasitair middel bij runderen en schapen.
AU779593B2 (en)	2005-02-03	Insecticidal combination effective against fleas on mammals, particularly cats and dogs
AU2005201861B2 (en)	2007-03-08	Insecticidal combination effective against fleas on mammals, particularly cats and dogs
AU2003257646B2 (en)	2006-03-30	Direct pour-on skin solution for anitparasitic use in cattle and sheep
SE531435C2 (sv)	2009-04-07	Insekticidförening mot loppor hos däggdjur, i synnerhet hundar och katter
HK1144387A (en)	2011-02-18	Insecticidal combination effective against fleas on mammals, particularly cats and dogs
AU7195800A (en)	2001-02-08	Direct pour-on skin solution for antiparasitic use in cattle and sheep
DK201370137A (da)	2013-03-11	Insekticid kombination mod lopper hos pattedyr