CA1057197A - Control of animal parasites with benzimidazoles - Google Patents
Control of animal parasites with benzimidazolesInfo
- Publication number
- CA1057197A CA1057197A CA220,909A CA220909A CA1057197A CA 1057197 A CA1057197 A CA 1057197A CA 220909 A CA220909 A CA 220909A CA 1057197 A CA1057197 A CA 1057197A
- Authority
- CA
- Canada
- Prior art keywords
- trifluoromethyl
- nitro
- compound
- composition
- animal
- 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.)
- Expired
Links
- 150000001556 benzimidazoles Chemical class 0.000 title abstract description 29
- 244000000054 animal parasite Species 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 241001465754 Metazoa Species 0.000 claims abstract description 87
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 230000000590 parasiticidal effect Effects 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 54
- -1 1,1,2,2-tetrafluoroethyl Chemical group 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 239000007943 implant Substances 0.000 claims description 16
- 238000009472 formulation Methods 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002671 adjuvant Substances 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 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 claims description 5
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 229940102213 injectable suspension Drugs 0.000 claims description 3
- 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 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 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 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- GXRHGBDDKIRHOD-UHFFFAOYSA-N phenyl 4-nitro-2,6-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)(F)C1=NC=2C([N+](=O)[O-])=CC(C(F)(F)F)=CC=2N1C(=O)OC1=CC=CC=C1 GXRHGBDDKIRHOD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- KZBLZIAMMOTEIG-UHFFFAOYSA-N propan-2-yl 4-nitro-2-(1,1,2,2-tetrafluoroethyl)-6-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)C(C(F)(F)C(F)F)=NC2=C1[N+]([O-])=O KZBLZIAMMOTEIG-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 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 claims 1
- MZBUUECWWVGYNT-UHFFFAOYSA-N 1-hydroxy-4-nitro-2-(1,1,2,2-tetrafluoroethyl)-6-(trifluoromethyl)benzimidazole Chemical compound C1=C(C(F)(F)F)C=C2N(O)C(C(F)(F)C(F)F)=NC2=C1[N+]([O-])=O MZBUUECWWVGYNT-UHFFFAOYSA-N 0.000 claims 1
- KZOLUUABNYRFHR-UHFFFAOYSA-N phenyl 2-chloro-5-(difluoromethyl)-4-nitro-6-(trifluoromethyl)benzimidazole-2-carboxylate Chemical compound N1=C2C([N+](=O)[O-])=C(C(F)F)C(C(F)(F)F)=CC2=NC1(Cl)C(=O)OC1=CC=CC=C1 KZOLUUABNYRFHR-UHFFFAOYSA-N 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract description 72
- 241000238876 Acari Species 0.000 abstract description 24
- 241000238631 Hexapoda Species 0.000 abstract description 11
- 239000002297 parasiticide Substances 0.000 abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
- 230000009885 systemic effect Effects 0.000 abstract description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 50
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 30
- 241000282472 Canis lupus familiaris Species 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 210000001519 tissue Anatomy 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 14
- 210000004369 blood Anatomy 0.000 description 14
- 239000008280 blood Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 241000258242 Siphonaptera Species 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 241000283690 Bos taurus Species 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 241000819999 Nymphes Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000920471 Lucilia caesar Species 0.000 description 8
- 206010052428 Wound Diseases 0.000 description 8
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 241000283086 Equidae Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000238682 Amblyomma americanum Species 0.000 description 6
- 241000202814 Cochliomyia hominivorax Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001494479 Pecora Species 0.000 description 6
- 241001494115 Stomoxys calcitrans Species 0.000 description 6
- 241000282887 Suidae Species 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 241000700198 Cavia Species 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 241001331845 Equus asinus x caballus Species 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 210000004767 rumen Anatomy 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000257186 Phormia regina Species 0.000 description 4
- 241000282849 Ruminantia Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 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 3
- 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 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241000545319 Ixodes canisuga Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 201000002266 mite infestation Diseases 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 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 2
- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000257226 Muscidae 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
- 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
- 239000000642 acaricide Substances 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 150000008061 acetanilides Chemical class 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 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
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- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- LZAVTPBNUUHZCP-UHFFFAOYSA-N n-[2,6-dinitro-4-(trifluoromethyl)phenyl]-2,2,2-trifluoroacetamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1NC(=O)C(F)(F)F LZAVTPBNUUHZCP-UHFFFAOYSA-N 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
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- 239000011593 sulfur Substances 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 2
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 2
- 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
- UZDGGZVJNCBGRU-UHFFFAOYSA-N 1-[7-nitro-2,5-bis(trifluoromethyl)benzimidazol-1-yl]ethanone Chemical compound FC(F)(F)C1=CC([N+]([O-])=O)=C2N(C(=O)C)C(C(F)(F)F)=NC2=C1 UZDGGZVJNCBGRU-UHFFFAOYSA-N 0.000 description 1
- IRSPCJLMPFDMGD-UHFFFAOYSA-N 1-hydroxybenzimidazole Chemical class C1=CC=C2N(O)C=NC2=C1 IRSPCJLMPFDMGD-UHFFFAOYSA-N 0.000 description 1
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- MXFMPTXDHSDMTI-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1 MXFMPTXDHSDMTI-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
- 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 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical class 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
- BQIQQUWARIJQJA-UHFFFAOYSA-N 3-morpholin-4-ylbutanoic acid Chemical compound OC(=O)CC(C)N1CCOCC1 BQIQQUWARIJQJA-UHFFFAOYSA-N 0.000 description 1
- WQRYZWVAWJMKPB-UHFFFAOYSA-N 3-nitro-5-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1N WQRYZWVAWJMKPB-UHFFFAOYSA-N 0.000 description 1
- DJLZIZLROPQZDE-UHFFFAOYSA-N 4-nitro-2,6-bis(trifluoromethyl)benzimidazole-1-carboxylic acid Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)O)C(C(F)(F)F)=NC2=C1[N+]([O-])=O DJLZIZLROPQZDE-UHFFFAOYSA-N 0.000 description 1
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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 |
|---|---|
| CA1057197A true CA1057197A (en) | 1979-06-26 |
Family
ID=27035924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,909A Expired CA1057197A (en) | 1974-03-11 | 1975-02-27 | Control of animal parasites with benzimidazoles |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6018643B2 (en, 2012) |
| BR (1) | BR7501418A (en, 2012) |
| CA (1) | CA1057197A (en, 2012) |
| CH (1) | CH628207A5 (en, 2012) |
| CS (1) | CS203978B2 (en, 2012) |
| DD (1) | DD119124A5 (en, 2012) |
| DE (1) | DE2509346A1 (en, 2012) |
| DK (1) | DK96075A (en, 2012) |
| FR (1) | FR2263771B1 (en, 2012) |
| GB (1) | GB1505846A (en, 2012) |
| IE (1) | IE40726B1 (en, 2012) |
| IL (1) | IL46671A (en, 2012) |
| IT (1) | IT1051745B (en, 2012) |
| NL (1) | NL7502846A (en, 2012) |
| SE (1) | SE7502661L (en, 2012) |
| ZA (1) | ZA751024B (en, 2012) |
Families Citing this family (7)
| 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 |
| DE4237597A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Substituierte Benzimidazole |
| DE4237617A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Verwendung von substituierten Benzimidazolen |
| DE4237557A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Substituierte Benzimidazole |
| DE4237548A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Substituierte Benzimidazole |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| CS203978B2 (en) | 1981-03-31 |
| CH628207A5 (en) | 1982-02-26 |
| FR2263771B1 (en, 2012) | 1978-07-28 |
| IL46671A0 (en) | 1975-05-22 |
| DK96075A (en, 2012) | 1975-09-12 |
| NL7502846A (nl) | 1975-09-15 |
| SE7502661L (en, 2012) | 1975-09-12 |
| IT1051745B (it) | 1981-05-20 |
| FR2263771A1 (en, 2012) | 1975-10-10 |
| AU7850375A (en) | 1976-08-26 |
| BR7501418A (pt) | 1975-12-09 |
| IE40726B1 (en) | 1979-08-01 |
| JPS50126832A (en, 2012) | 1975-10-06 |
| IE40726L (en) | 1975-09-11 |
| IL46671A (en) | 1978-09-29 |
| ZA751024B (en) | 1976-01-28 |
| DD119124A5 (en, 2012) | 1976-04-12 |
| DE2509346A1 (de) | 1975-09-18 |
| GB1505846A (en) | 1978-03-30 |
| JPS6018643B2 (ja) | 1985-05-11 |
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