NL1005673C2 - Oplossing voor directe aanbrenging op de huid voor gebruik als anti-parasitair middel bij runderen en schapen. - Google Patents
Oplossing voor directe aanbrenging op de huid voor gebruik als anti-parasitair middel bij runderen en schapen. Download PDFInfo
- Publication number
- NL1005673C2 NL1005673C2 NL1005673A NL1005673A NL1005673C2 NL 1005673 C2 NL1005673 C2 NL 1005673C2 NL 1005673 A NL1005673 A NL 1005673A NL 1005673 A NL1005673 A NL 1005673A NL 1005673 C2 NL1005673 C2 NL 1005673C2
- Authority
- NL
- Netherlands
- Prior art keywords
- alkyl
- group
- haloalkyl
- compound
- formula
- Prior art date
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- 241000283690 Bos taurus Species 0.000 title claims description 21
- 241001494479 Pecora Species 0.000 title claims description 21
- 239000003096 antiparasitic agent Substances 0.000 title description 4
- 229940125687 antiparasitic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000001188 haloalkyl group Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 241001465754 Metazoa Species 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 39
- -1 4,5-dicyanimidazol-2-yl Chemical group 0.000 claims description 24
- 241000238680 Rhipicephalus microplus Species 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 244000045947 parasite Species 0.000 claims description 19
- 241000238876 Acari Species 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 10
- 241001674048 Phthiraptera Species 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000003795 chemical substances by application 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 210000004209 hair Anatomy 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 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 Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 238000003307 slaughter Methods 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000004359 castor oil Substances 0.000 claims description 4
- 235000019438 castor oil Nutrition 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 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 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 244000060011 Cocos nucifera Species 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 2
- 229920000742 Cotton Polymers 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
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 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
- 235000019483 Peanut oil Nutrition 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
- 235000019486 Sunflower oil Nutrition 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
- 125000001931 aliphatic group Chemical group 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
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 229960003237 betaine Drugs 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
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229940031769 diisobutyl adipate Drugs 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 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
- 229940100242 glycol stearate Drugs 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 239000008169 grapeseed oil Substances 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 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
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 235000019271 petrolatum Nutrition 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 125000005372 silanol group Chemical group 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 2
- 229920001027 sodium carboxymethylcellulose Polymers 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical class [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 229940029614 triethanolamine stearate Drugs 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 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 1
- 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 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 description 15
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 15
- 229940068196 placebo Drugs 0.000 description 9
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000257232 Haematobia irritans Species 0.000 description 2
- 241000920471 Lucilia caesar Species 0.000 description 2
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- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
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- 238000003892 spreading Methods 0.000 description 2
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-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
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- 241000972142 Boophis <genus> Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000202828 Dermatobia hominis Species 0.000 description 1
- 241001113970 Linognathus Species 0.000 description 1
- 241000257166 Lucilia cuprina Species 0.000 description 1
- 241000736227 Lucilia sericata Species 0.000 description 1
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- 241000509427 Sarcoptes scabiei Species 0.000 description 1
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- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 description 1
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- 238000009792 diffusion process Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000255 pathogenic effect Toxicity 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9604209 | 1996-03-29 | ||
| FR9604209A FR2746595B1 (fr) | 1996-03-29 | 1996-03-29 | Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins |
| US69217896A | 1996-08-05 | 1996-08-05 | |
| US69217896 | 1996-08-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NL1005673A1 NL1005673A1 (nl) | 1997-09-30 |
| NL1005673C2 true NL1005673C2 (nl) | 1997-11-18 |
Family
ID=26232632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1005673A NL1005673C2 (nl) | 1996-03-29 | 1997-03-27 | Oplossing voor directe aanbrenging op de huid voor gebruik als anti-parasitair middel bij runderen en schapen. |
Country Status (20)
| Country | Link |
|---|---|
| AT (2) | AT504042A1 (fr) |
| AU (1) | AU2513097A (fr) |
| BE (1) | BE1010483A5 (fr) |
| BR (1) | BR9702162A (fr) |
| CA (1) | CA2222675C (fr) |
| CH (1) | CH692894A8 (fr) |
| DE (1) | DE19780396B3 (fr) |
| DK (1) | DK177400B1 (fr) |
| ES (1) | ES2143389B1 (fr) |
| FI (1) | FI119042B (fr) |
| FR (1) | FR2747015B1 (fr) |
| GB (1) | GB2318512B (fr) |
| GR (1) | GR1002910B (fr) |
| IE (1) | IE970215A1 (fr) |
| IT (1) | IT1291699B1 (fr) |
| LU (1) | LU90177B1 (fr) |
| NL (1) | NL1005673C2 (fr) |
| NO (1) | NO324071B1 (fr) |
| SE (1) | SE523761C2 (fr) |
| WO (1) | WO1997036486A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW524667B (en) * | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| AUPQ441699A0 (en) * | 1999-12-02 | 2000-01-06 | Eli Lilly And Company | Pour-on formulations |
| WO2001095723A1 (fr) * | 2000-06-15 | 2001-12-20 | Ssl International Plc | Composition parasiticide |
| DE10063865A1 (de) * | 2000-12-21 | 2002-06-27 | Bayer Ag | Verwendung von Pyrazoloximen als Parasitizide |
| GB0329314D0 (en) | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
| US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
| 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045424A1 (fr) * | 1980-08-02 | 1982-02-10 | Bayer Ag | Formulations "pour-on" actives contre les tiques |
| EP0295117A1 (fr) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Dérivés de N-phénylpyrazoles |
| EP0296381A1 (fr) * | 1987-06-12 | 1988-12-28 | Bayer Ag | Méthylamino-5-aryl-1 pyrazoles substitués |
| EP0412849A2 (fr) * | 1989-08-10 | 1991-02-13 | AgrEvo UK Limited | Azoles comme pesticides |
| EP0500209A1 (fr) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | 1-(2-Pyridyl)pyrazoles pesticides |
| WO1996016544A2 (fr) * | 1994-11-30 | 1996-06-06 | Rhone-Poulenc Agrochimie | Composition emulsionnable destinee a la lutte contre les insectes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| DE4414333A1 (de) * | 1994-04-25 | 1995-10-26 | Bayer Ag | Substituierte Pyridylpyrazole |
-
1997
- 1997-03-20 IE IE970215A patent/IE970215A1/en not_active IP Right Cessation
- 1997-03-26 CH CH02791/97A patent/CH692894A8/fr not_active IP Right Cessation
- 1997-03-26 DE DE19780396T patent/DE19780396B3/de not_active Expired - Lifetime
- 1997-03-26 WO PCT/FR1997/000542 patent/WO1997036486A1/fr not_active Ceased
- 1997-03-26 FR FR9703708A patent/FR2747015B1/fr not_active Expired - Lifetime
- 1997-03-26 GB GB9725003A patent/GB2318512B/en not_active Expired - Lifetime
- 1997-03-26 AU AU25130/97A patent/AU2513097A/en not_active Abandoned
- 1997-03-26 GR GR970100110A patent/GR1002910B/el not_active IP Right Cessation
- 1997-03-26 ES ES009750029A patent/ES2143389B1/es not_active Expired - Fee Related
- 1997-03-26 AT AT0900497A patent/AT504042A1/de not_active Application Discontinuation
- 1997-03-26 BR BR9702162A patent/BR9702162A/pt active IP Right Grant
- 1997-03-26 CA CA002222675A patent/CA2222675C/fr not_active Expired - Lifetime
- 1997-03-27 IT IT97TO000260A patent/IT1291699B1/it active IP Right Grant
- 1997-03-27 BE BE9700276A patent/BE1010483A5/fr active
- 1997-03-27 NL NL1005673A patent/NL1005673C2/nl not_active IP Right Cessation
- 1997-11-24 SE SE9704303A patent/SE523761C2/sv not_active IP Right Cessation
- 1997-11-26 LU LU90177A patent/LU90177B1/fr active
- 1997-11-27 DK DKPA199701363A patent/DK177400B1/da not_active IP Right Cessation
- 1997-11-27 FI FI974353A patent/FI119042B/fi not_active IP Right Cessation
- 1997-11-27 NO NO19975473A patent/NO324071B1/no not_active IP Right Cessation
-
2009
- 2009-09-04 AT ATA1395/2009A patent/AT506843B1/de not_active IP Right Cessation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045424A1 (fr) * | 1980-08-02 | 1982-02-10 | Bayer Ag | Formulations "pour-on" actives contre les tiques |
| EP0295117A1 (fr) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Dérivés de N-phénylpyrazoles |
| EP0296381A1 (fr) * | 1987-06-12 | 1988-12-28 | Bayer Ag | Méthylamino-5-aryl-1 pyrazoles substitués |
| EP0412849A2 (fr) * | 1989-08-10 | 1991-02-13 | AgrEvo UK Limited | Azoles comme pesticides |
| EP0500209A1 (fr) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | 1-(2-Pyridyl)pyrazoles pesticides |
| WO1996016544A2 (fr) * | 1994-11-30 | 1996-06-06 | Rhone-Poulenc Agrochimie | Composition emulsionnable destinee a la lutte contre les insectes |
Non-Patent Citations (1)
| Title |
|---|
| "EXTENDED EFFICACY SPECTRUM OF AZOLE PESTICIDES", RESEARCH DISCLOSURE, no. 380, 1 December 1995 (1995-12-01), pages 802, XP000549823 * |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AD1B | A search report has been drawn up | ||
| PD2B | A search report has been drawn up | ||
| TD | Modifications of names of proprietors of patents |
Owner name: MERIAL |
|
| MK | Patent expired because of reaching the maximum lifetime of a patent |
Effective date: 20170326 |