CH618323A5 - Pesticidal composition for controlling ectoparasites, process for its preparation and its use - Google Patents
Pesticidal composition for controlling ectoparasites, process for its preparation and its use Download PDFInfo
- Publication number
- CH618323A5 CH618323A5 CH1028675A CH1028675A CH618323A5 CH 618323 A5 CH618323 A5 CH 618323A5 CH 1028675 A CH1028675 A CH 1028675A CH 1028675 A CH1028675 A CH 1028675A CH 618323 A5 CH618323 A5 CH 618323A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- formula
- hydroxy
- nitro
- parasiticidal
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 25
- 244000078703 ectoparasite Species 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000000361 pesticidal effect Effects 0.000 title 1
- 241001465754 Metazoa Species 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 239000007943 implant Substances 0.000 claims description 20
- -1 di-fluoromethyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000000590 parasiticidal effect Effects 0.000 claims description 8
- 239000003096 antiparasitic agent Substances 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- VHSHFLMRNNEJDL-UHFFFAOYSA-N 2-chloro-5-(difluoromethyl)-1-hydroxy-4-nitro-6-(trifluoromethyl)benzimidazole Chemical compound FC(F)C1=C(C(F)(F)F)C=C2N(O)C(Cl)=NC2=C1[N+]([O-])=O VHSHFLMRNNEJDL-UHFFFAOYSA-N 0.000 claims description 2
- AVJMVANOZBCIIE-UHFFFAOYSA-N 5-chloro-1-hydroxy-7-nitro-2-(trifluoromethyl)benzimidazole Chemical compound ClC1=CC([N+]([O-])=O)=C2N(O)C(C(F)(F)F)=NC2=C1 AVJMVANOZBCIIE-UHFFFAOYSA-N 0.000 claims description 2
- CNFKLHRJIPFAAC-UHFFFAOYSA-N 6-chloro-1-hydroxy-4-nitro-2-(1,1,2,2-tetrafluoroethyl)benzimidazole Chemical compound C1=C(Cl)C=C2N(O)C(C(F)(F)C(F)F)=NC2=C1[N+]([O-])=O CNFKLHRJIPFAAC-UHFFFAOYSA-N 0.000 claims description 2
- VHASYZMQULGDCJ-UHFFFAOYSA-N 6-chloro-5-(difluoromethyl)-2-(1,1,2,2,3,3,3-heptafluoropropyl)-1-hydroxy-4-nitrobenzimidazole Chemical compound ClC=1C(=C(C2=C(N(C(=N2)C(C(C(F)(F)F)(F)F)(F)F)O)C1)[N+](=O)[O-])C(F)F VHASYZMQULGDCJ-UHFFFAOYSA-N 0.000 claims description 2
- UGWOQNIUBCAWPW-UHFFFAOYSA-N 7-(difluoromethyl)-1-hydroxy-5-nitro-2-(1,1,2,2,2-pentafluoroethyl)benzimidazole Chemical compound [O-][N+](=O)C1=CC(C(F)F)=C2N(O)C(C(F)(F)C(F)(F)F)=NC2=C1 UGWOQNIUBCAWPW-UHFFFAOYSA-N 0.000 claims description 2
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 244000045947 parasite Species 0.000 description 44
- 239000008280 blood Substances 0.000 description 34
- 210000004369 blood Anatomy 0.000 description 34
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 17
- 210000001519 tissue Anatomy 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 150000001556 benzimidazoles Chemical class 0.000 description 11
- 241000283690 Bos taurus Species 0.000 description 10
- 241000819999 Nymphes Species 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 210000003491 skin Anatomy 0.000 description 9
- 206010061217 Infestation Diseases 0.000 description 8
- 241000238876 Acari Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 241000255632 Tabanus atratus Species 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000257186 Phormia regina Species 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 201000002266 mite infestation Diseases 0.000 description 5
- 230000000149 penetrating effect Effects 0.000 description 5
- 241000255925 Diptera Species 0.000 description 4
- 241000283086 Equidae Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241001494479 Pecora 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
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 210000000090 ruminant stomach Anatomy 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001494115 Stomoxys calcitrans Species 0.000 description 3
- 241000282887 Suidae Species 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 210000003780 hair follicle Anatomy 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000193880 Demodex folliculorum Species 0.000 description 2
- 241001331845 Equus asinus x caballus Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000509427 Sarcoptes scabiei Species 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 244000000054 animal parasite Species 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000001418 larval effect Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- IRSPCJLMPFDMGD-UHFFFAOYSA-N 1-hydroxybenzimidazole Chemical class C1=CC=C2N(O)C=NC2=C1 IRSPCJLMPFDMGD-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
- 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
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000238682 Amblyomma americanum Species 0.000 description 1
- 241001480737 Amblyomma maculatum Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001480752 Argas persicus Species 0.000 description 1
- 241000322476 Bovicola bovis Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241000282832 Camelidae Species 0.000 description 1
- 241000282421 Canidae Species 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241000202814 Cochliomyia hominivorax Species 0.000 description 1
- 241000933849 Cochliomyia macellaria Species 0.000 description 1
- 241001128002 Demodex canis Species 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- 241001549209 Echidnophaga gallinacea Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000692264 Gasterophilus haemorrhoidalis Species 0.000 description 1
- 241001660201 Gasterophilus intestinalis Species 0.000 description 1
- 241001502121 Glossina brevipalpis Species 0.000 description 1
- 241000446881 Haemaphysalis bispinosa Species 0.000 description 1
- 241000257232 Haematobia irritans Species 0.000 description 1
- 241000670091 Haematopinus suis Species 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 229920001732 Lignosulfonate Chemical class 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 241000257166 Lucilia cuprina Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000771994 Melophagus ovinus Species 0.000 description 1
- 241001480756 Otobius megnini Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000193418 Paenibacillus larvae Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241001097374 Pselliopus cinctus Species 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 206010039207 Rocky Mountain Spotted Fever Diseases 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 229940125687 antiparasitic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- CXPOFJRHCFPDRI-UHFFFAOYSA-N dodecylbenzene;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 CXPOFJRHCFPDRI-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 125000005642 phosphothioate group Chemical group 0.000 description 1
- 239000012165 plant wax Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/584,991 US3980784A (en) | 1974-12-02 | 1975-06-12 | Control of animal parasites with benzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618323A5 true CH618323A5 (en) | 1980-07-31 |
Family
ID=24339613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1028675A CH618323A5 (en) | 1975-06-12 | 1975-08-06 | Pesticidal composition for controlling ectoparasites, process for its preparation and its use |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51148031A (cs) |
| AT (1) | AT348822B (cs) |
| AU (1) | AU505294B2 (cs) |
| BE (1) | BE832291A (cs) |
| BR (1) | BR7505218A (cs) |
| CH (1) | CH618323A5 (cs) |
| CS (1) | CS203979B2 (cs) |
| DD (1) | DD126963A5 (cs) |
| DE (1) | DE2535966A1 (cs) |
| DK (1) | DK370575A (cs) |
| FR (1) | FR2310758A2 (cs) |
| GB (1) | GB1520763A (cs) |
| IE (1) | IE41449B1 (cs) |
| IL (1) | IL47889A (cs) |
| IT (1) | IT1067656B (cs) |
| NL (1) | NL7509399A (cs) |
| PH (1) | PH11860A (cs) |
| SE (1) | SE7508968L (cs) |
| ZA (1) | ZA755250B (cs) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1770658A1 (de) * | 1968-06-19 | 1971-11-11 | Hoechst Ag | N-Hydroxi-benzimidazole,ihre Herstellung und Verwendung als Herbicide |
| DE2022504A1 (de) * | 1970-05-08 | 1971-11-25 | Hoechst Ag | Benzimidazolderivate,ihre Herstellung und Verwendung als Akarizide |
-
1975
- 1975-08-06 CH CH1028675A patent/CH618323A5/de not_active IP Right Cessation
- 1975-08-07 NL NL7509399A patent/NL7509399A/xx not_active Application Discontinuation
- 1975-08-07 IL IL47889A patent/IL47889A/xx unknown
- 1975-08-08 SE SE7508968A patent/SE7508968L/xx not_active Application Discontinuation
- 1975-08-08 AU AU83816/75A patent/AU505294B2/en not_active Expired
- 1975-08-08 PH PH17459A patent/PH11860A/en unknown
- 1975-08-11 IE IE1784/75A patent/IE41449B1/en unknown
- 1975-08-11 BE BE1006818A patent/BE832291A/xx not_active IP Right Cessation
- 1975-08-12 DE DE19752535966 patent/DE2535966A1/de not_active Withdrawn
- 1975-08-12 IT IT26316/75A patent/IT1067656B/it active
- 1975-08-12 GB GB33490/75A patent/GB1520763A/en not_active Expired
- 1975-08-14 CS CS755599A patent/CS203979B2/cs unknown
- 1975-08-14 AT AT634675A patent/AT348822B/de not_active IP Right Cessation
- 1975-08-14 FR FR7525396A patent/FR2310758A2/fr active Granted
- 1975-08-15 DD DD187879A patent/DD126963A5/xx unknown
- 1975-08-15 BR BR7505218D patent/BR7505218A/pt unknown
- 1975-08-15 DK DK370575A patent/DK370575A/da not_active Application Discontinuation
- 1975-08-15 ZA ZA00755250A patent/ZA755250B/xx unknown
- 1975-08-16 JP JP50099729A patent/JPS51148031A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL47889A0 (en) | 1975-11-25 |
| DK370575A (da) | 1976-12-13 |
| AU505294B2 (en) | 1979-11-15 |
| IL47889A (en) | 1978-09-29 |
| DD126963A5 (cs) | 1977-08-24 |
| DE2535966A1 (de) | 1976-12-23 |
| CS203979B2 (en) | 1981-03-31 |
| ZA755250B (en) | 1976-09-29 |
| FR2310758B2 (cs) | 1978-09-01 |
| PH11860A (en) | 1978-08-03 |
| JPS51148031A (en) | 1976-12-18 |
| IT1067656B (it) | 1985-03-16 |
| AT348822B (de) | 1979-03-12 |
| SE7508968L (sv) | 1976-12-13 |
| GB1520763A (en) | 1978-08-09 |
| BR7505218A (pt) | 1977-03-08 |
| AU8381675A (en) | 1977-02-10 |
| ATA634675A (de) | 1978-07-15 |
| IE41449B1 (en) | 1980-01-02 |
| FR2310758A2 (fr) | 1976-12-10 |
| NL7509399A (nl) | 1976-12-14 |
| BE832291A (fr) | 1976-02-11 |
| IE41449L (en) | 1976-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |