DE2509346A1 - Parasiticides mittel - Google Patents
Parasiticides mittelInfo
- Publication number
- DE2509346A1 DE2509346A1 DE19752509346 DE2509346A DE2509346A1 DE 2509346 A1 DE2509346 A1 DE 2509346A1 DE 19752509346 DE19752509346 DE 19752509346 DE 2509346 A DE2509346 A DE 2509346A DE 2509346 A1 DE2509346 A1 DE 2509346A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- benzimidazole
- trifluoromethyl
- active ingredient
- bis
- 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.)
- Withdrawn
Links
- 239000003795 chemical substances by application Substances 0.000 title description 10
- 239000002297 parasiticide Substances 0.000 title description 4
- 241001465754 Metazoa Species 0.000 description 74
- 244000045947 parasite Species 0.000 description 64
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 35
- 238000000034 method Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- -1 1,1,2,2-tetrafluoroethyl Chemical group 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 26
- 241000238876 Acari Species 0.000 description 25
- 150000001556 benzimidazoles Chemical class 0.000 description 25
- 241000282472 Canis lupus familiaris Species 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- 210000001519 tissue Anatomy 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000007943 implant Substances 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
- 241000283690 Bos taurus Species 0.000 description 12
- 239000008280 blood Substances 0.000 description 12
- 210000004369 blood Anatomy 0.000 description 12
- 241000258242 Siphonaptera Species 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 230000001418 larval effect Effects 0.000 description 11
- 241000819999 Nymphes Species 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000007920 subcutaneous administration Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000255925 Diptera Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241000257226 Muscidae Species 0.000 description 7
- 241001494479 Pecora Species 0.000 description 7
- 206010052428 Wound Diseases 0.000 description 7
- 208000027418 Wounds and injury Diseases 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000283086 Equidae Species 0.000 description 6
- 241000282887 Suidae Species 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ABDCPNNAYAMHOX-UHFFFAOYSA-N 1-hydroxy-4-nitro-2,6-bis(trifluoromethyl)benzimidazole Chemical compound C1=C(C(F)(F)F)C=C2N(O)C(C(F)(F)F)=NC2=C1[N+]([O-])=O ABDCPNNAYAMHOX-UHFFFAOYSA-N 0.000 description 5
- IRSPCJLMPFDMGD-UHFFFAOYSA-N 1-hydroxybenzimidazole Chemical compound C1=CC=C2N(O)C=NC2=C1 IRSPCJLMPFDMGD-UHFFFAOYSA-N 0.000 description 5
- 241000257161 Calliphoridae Species 0.000 description 5
- 241000700198 Cavia Species 0.000 description 5
- 241001331845 Equus asinus x caballus Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241001494115 Stomoxys calcitrans Species 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 210000004767 rumen Anatomy 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- MXFMPTXDHSDMTI-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1 MXFMPTXDHSDMTI-UHFFFAOYSA-N 0.000 description 4
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000193880 Demodex folliculorum Species 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 241000282849 Ruminantia Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000003857 carboxamides Chemical class 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000000590 parasiticidal effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229940035044 sorbitan monolaurate Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241000920471 Lucilia caesar Species 0.000 description 3
- 241000257186 Phormia regina Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 244000000054 animal parasite Species 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- ZWPAHGUARPVOIZ-UHFFFAOYSA-N 2-chloro-5-(difluoromethyl)-4-nitro-6-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=C(C(F)F)C(C(F)(F)F)=CC2=C1N=C(Cl)N2 ZWPAHGUARPVOIZ-UHFFFAOYSA-N 0.000 description 2
- NBODKGMTUVCSEI-UHFFFAOYSA-N 4-nitro-2,6-bis(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC2=C1N=C(C(F)(F)F)N2 NBODKGMTUVCSEI-UHFFFAOYSA-N 0.000 description 2
- 241000272878 Apodiformes Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000257191 Oestridae Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- 241000255632 Tabanus atratus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 235000005686 eating Nutrition 0.000 description 2
- 244000079386 endoparasite Species 0.000 description 2
- QWZSINSKXDSFBT-UHFFFAOYSA-N ethyl 2-chloro-5-(difluoromethyl)-4-nitro-6-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)C1=C(C(F)(F)F)C=C2N(C(=O)OCC)C(Cl)=NC2=C1[N+]([O-])=O QWZSINSKXDSFBT-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 210000000003 hoof Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- YXUFVUMORYXDOG-UHFFFAOYSA-N propan-2-yl 4-nitro-2,6-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)C(C(F)(F)F)=NC2=C1[N+]([O-])=O YXUFVUMORYXDOG-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 1
- RRITUYYRGPJTAW-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-nitro-2,6-bis(trifluoromethyl)benzimidazole Chemical compound FC(F)(F)C1=NC=2C([N+](=O)[O-])=CC(C(F)(F)F)=CC=2N1S(=O)(=O)C1=CC=CC=C1 RRITUYYRGPJTAW-UHFFFAOYSA-N 0.000 description 1
- YWBJNDLUMQNTOD-UHFFFAOYSA-N 1-(benzenesulfonyl)benzimidazole Chemical compound C1=NC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 YWBJNDLUMQNTOD-UHFFFAOYSA-N 0.000 description 1
- MSXFYDACPRWHMI-UHFFFAOYSA-N 1-[4-nitro-2,6-bis(trifluoromethyl)benzimidazol-1-yl]ethanone Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)C)C(C(F)(F)F)=NC2=C1[N+]([O-])=O MSXFYDACPRWHMI-UHFFFAOYSA-N 0.000 description 1
- XGBINPWBEANVBU-UHFFFAOYSA-N 1-[4-nitro-2,6-bis(trifluoromethyl)benzimidazol-1-yl]hexan-1-one Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)CCCCC)C(C(F)(F)F)=NC2=C1[N+]([O-])=O XGBINPWBEANVBU-UHFFFAOYSA-N 0.000 description 1
- KSQBGKRVNAJRAJ-UHFFFAOYSA-N 1-ethoxy-4-nitro-2-(1,1,2,2,2-pentafluoroethyl)-6-(trifluoromethyl)benzimidazole Chemical compound C1=C(C(F)(F)F)C=C2N(OCC)C(C(F)(F)C(F)(F)F)=NC2=C1[N+]([O-])=O KSQBGKRVNAJRAJ-UHFFFAOYSA-N 0.000 description 1
- DUYNLNLTKKOTII-UHFFFAOYSA-N 1-methoxy-4-nitro-2-(1,1,2,2-tetrafluoroethyl)-6-(trifluoromethyl)benzimidazole Chemical compound C1=C(C(F)(F)F)C=C2N(OC)C(C(F)(F)C(F)F)=NC2=C1[N+]([O-])=O DUYNLNLTKKOTII-UHFFFAOYSA-N 0.000 description 1
- 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
- RHXSYTACTOMVLJ-UHFFFAOYSA-N 1H-benzimidazole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=NC2=C1 RHXSYTACTOMVLJ-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- VACNDKUQVLNNLD-UHFFFAOYSA-N 2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O VACNDKUQVLNNLD-UHFFFAOYSA-N 0.000 description 1
- UFOXBWPONOTEDS-UHFFFAOYSA-N 2-(trifluoromethylsulfanyl)benzimidazole-1-carboxamide Chemical compound FC(SC1=NC2=C(N1C(=O)N)C=CC=C2)(F)F UFOXBWPONOTEDS-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- HFHAVERNVFNSHL-UHFFFAOYSA-N 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl HFHAVERNVFNSHL-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VSKRLWVUULXUMF-UHFFFAOYSA-N 3-chloro-5-nitrobenzene-1,2-diamine Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1N VSKRLWVUULXUMF-UHFFFAOYSA-N 0.000 description 1
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 1
- DIDBYIUVQXSFCL-UHFFFAOYSA-N 4-nitro-2,6-bis(trifluoromethyl)-1h-benzimidazole;sodium Chemical compound [Na].[O-][N+](=O)C1=CC(C(F)(F)F)=CC2=C1N=C(C(F)(F)F)N2 DIDBYIUVQXSFCL-UHFFFAOYSA-N 0.000 description 1
- XDFITJCWAFYZDO-UHFFFAOYSA-N 4-nitro-2-(1,1,2,2,2-pentafluoroethyl)-6-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC2=C1NC(C(F)(F)C(F)(F)F)=N2 XDFITJCWAFYZDO-UHFFFAOYSA-N 0.000 description 1
- FIZOLKMBQRTOCM-UHFFFAOYSA-N 5-chloro-1-n-(difluoromethyl)-3-nitrobenzene-1,2-diamine Chemical compound NC1=C(NC(F)F)C=C(Cl)C=C1[N+]([O-])=O FIZOLKMBQRTOCM-UHFFFAOYSA-N 0.000 description 1
- MJOCIFDXUKTLDN-UHFFFAOYSA-N 5-nitro-2,6-bis(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(C(F)(F)F)C([N+](=O)[O-])=CC2=C1N=C(C(F)(F)F)N2 MJOCIFDXUKTLDN-UHFFFAOYSA-N 0.000 description 1
- STOJWTVNHAJLBI-UHFFFAOYSA-N 6-chloro-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Cl)=CC2=C1N=C(C(F)(F)F)N2 STOJWTVNHAJLBI-UHFFFAOYSA-N 0.000 description 1
- KNWBYYSQLWZITM-UHFFFAOYSA-N 6-chloro-5-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1NC(C(F)(F)F)=N2 KNWBYYSQLWZITM-UHFFFAOYSA-N 0.000 description 1
- 241001480737 Amblyomma maculatum Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282832 Camelidae Species 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- FLMCKQJLEIUVRK-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(difluoromethyl)-4-nitro-6-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)C1=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)C(Cl)=NC2=C1[N+]([O-])=O FLMCKQJLEIUVRK-UHFFFAOYSA-N 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- XCIHDNJITPNKED-UHFFFAOYSA-N trifluoromethyl benzimidazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(F)(F)F)C=NC2=C1 XCIHDNJITPNKED-UHFFFAOYSA-N 0.000 description 1
- 206010061393 typhus Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—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
- A01N47/08—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<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45012874A | 1974-03-11 | 1974-03-11 | |
| US52860674A | 1974-12-02 | 1974-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2509346A1 true DE2509346A1 (de) | 1975-09-18 |
Family
ID=27035924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752509346 Withdrawn DE2509346A1 (de) | 1974-03-11 | 1975-03-04 | Parasiticides mittel |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6018643B2 (en:Method) |
| BR (1) | BR7501418A (en:Method) |
| CA (1) | CA1057197A (en:Method) |
| CH (1) | CH628207A5 (en:Method) |
| CS (1) | CS203978B2 (en:Method) |
| DD (1) | DD119124A5 (en:Method) |
| DE (1) | DE2509346A1 (en:Method) |
| DK (1) | DK96075A (en:Method) |
| FR (1) | FR2263771B1 (en:Method) |
| GB (1) | GB1505846A (en:Method) |
| IE (1) | IE40726B1 (en:Method) |
| IL (1) | IL46671A (en:Method) |
| IT (1) | IT1051745B (en:Method) |
| NL (1) | NL7502846A (en:Method) |
| SE (1) | SE7502661L (en:Method) |
| ZA (1) | ZA751024B (en:Method) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994011349A1 (de) * | 1992-11-06 | 1994-05-26 | Bayer Aktiengesellschaft | 2-fluoralkyl-substituierte benzimidazole, ihre herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
| WO1994011351A1 (de) * | 1992-11-06 | 1994-05-26 | Bayer Aktiengesellschaft | 2-perhalogenalkyl-substituierte benzimidazole, ihre herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
| WO1994011350A1 (de) * | 1992-11-06 | 1994-05-26 | Bayer Aktiengesellschaft | 2-fluoralkyl-substituierte benzimidazole, ihre herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621301A1 (de) * | 1986-06-25 | 1988-01-07 | Bayer Ag | 2-trifluormethyl-benzimidazole |
| BG95755A (bg) * | 1991-01-19 | 1993-12-24 | Hoechst Aktiengesellschaft | Метод за получаване на препаративна форма за приложение чрез поливане на антихелминтни средства |
| DE4237617A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Verwendung von substituierten Benzimidazolen |
| EP2752579A4 (en) | 2011-09-02 | 2015-06-24 | Napone Co Ltd | ROTARY ASSISTANCE DEVICE, ROTATIONAL ASSISTANCE PROCESS AND POWER GENERATING DEVICE |
-
1975
- 1975-02-18 ZA ZA00751024A patent/ZA751024B/xx unknown
- 1975-02-20 IL IL46671A patent/IL46671A/xx unknown
- 1975-02-27 CA CA220,909A patent/CA1057197A/en not_active Expired
- 1975-03-03 IE IE444/75A patent/IE40726B1/xx unknown
- 1975-03-04 DE DE19752509346 patent/DE2509346A1/de not_active Withdrawn
- 1975-03-07 DD DD184648A patent/DD119124A5/xx unknown
- 1975-03-10 SE SE7502661A patent/SE7502661L/xx not_active Application Discontinuation
- 1975-03-10 GB GB9843/75A patent/GB1505846A/en not_active Expired
- 1975-03-10 IT IT21092/75A patent/IT1051745B/it active
- 1975-03-10 DK DK96075*#A patent/DK96075A/da not_active Application Discontinuation
- 1975-03-11 NL NL7502846A patent/NL7502846A/xx not_active Application Discontinuation
- 1975-03-11 BR BR1418/75A patent/BR7501418A/pt unknown
- 1975-03-11 FR FR7507561A patent/FR2263771B1/fr not_active Expired
- 1975-03-11 CH CH306675A patent/CH628207A5/de not_active IP Right Cessation
- 1975-03-11 JP JP50030010A patent/JPS6018643B2/ja not_active Expired
- 1975-03-11 CS CS751633A patent/CS203978B2/cs unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994011349A1 (de) * | 1992-11-06 | 1994-05-26 | Bayer Aktiengesellschaft | 2-fluoralkyl-substituierte benzimidazole, ihre herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
| WO1994011351A1 (de) * | 1992-11-06 | 1994-05-26 | Bayer Aktiengesellschaft | 2-perhalogenalkyl-substituierte benzimidazole, ihre herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
| WO1994011350A1 (de) * | 1992-11-06 | 1994-05-26 | Bayer Aktiengesellschaft | 2-fluoralkyl-substituierte benzimidazole, ihre herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CS203978B2 (en) | 1981-03-31 |
| CH628207A5 (en) | 1982-02-26 |
| FR2263771B1 (en:Method) | 1978-07-28 |
| IL46671A0 (en) | 1975-05-22 |
| DK96075A (en:Method) | 1975-09-12 |
| NL7502846A (nl) | 1975-09-15 |
| SE7502661L (en:Method) | 1975-09-12 |
| IT1051745B (it) | 1981-05-20 |
| FR2263771A1 (en:Method) | 1975-10-10 |
| AU7850375A (en) | 1976-08-26 |
| BR7501418A (pt) | 1975-12-09 |
| IE40726B1 (en) | 1979-08-01 |
| JPS50126832A (en:Method) | 1975-10-06 |
| IE40726L (en) | 1975-09-11 |
| IL46671A (en) | 1978-09-29 |
| ZA751024B (en) | 1976-01-28 |
| DD119124A5 (en:Method) | 1976-04-12 |
| CA1057197A (en) | 1979-06-26 |
| GB1505846A (en) | 1978-03-30 |
| JPS6018643B2 (ja) | 1985-05-11 |
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