DE2405732A1 - Ekto- und endoparasitenmittel - Google Patents
Ekto- und endoparasitenmittelInfo
- Publication number
- DE2405732A1 DE2405732A1 DE19742405732 DE2405732A DE2405732A1 DE 2405732 A1 DE2405732 A1 DE 2405732A1 DE 19742405732 DE19742405732 DE 19742405732 DE 2405732 A DE2405732 A DE 2405732A DE 2405732 A1 DE2405732 A1 DE 2405732A1
- Authority
- DE
- Germany
- Prior art keywords
- loo
- isocyanate
- thiobarbituric acid
- methyl
- chloro
- 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.)
- Pending
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 6
- 244000078703 ectoparasite Species 0.000 title abstract description 5
- BEWKSQPRIYJQHD-UHFFFAOYSA-N 4,6-dioxo-2-sulfanylidene-1,3-diazinane-5-carboxamide Chemical compound NC(=O)C1C(=O)NC(=S)NC1=O BEWKSQPRIYJQHD-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 4
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 13
- 239000000969 carrier Substances 0.000 claims description 6
- 244000079386 endoparasite Species 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- -1 alkyl alkoxyalkyl Chemical group 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 6
- 241000238631 Hexapoda Species 0.000 abstract description 3
- 241000239223 Arachnida Species 0.000 abstract description 2
- 230000002013 molluscicidal effect Effects 0.000 abstract description 2
- SEOTWAPVCWHREV-UHFFFAOYSA-N N-(4-chlorophenyl)-1,3-dimethyl-4,6-dioxo-2-sulfanylidene-1,3-diazinane-5-carboxamide Chemical compound ClC1=CC=C(NC(=O)C2C(N(C(N(C2=O)C)=S)C)=O)C=C1 SEOTWAPVCWHREV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003096 antiparasitic agent Substances 0.000 abstract 1
- 229940125687 antiparasitic agent Drugs 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 49
- 239000000460 chlorine Substances 0.000 description 39
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 241001465754 Metazoa Species 0.000 description 18
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 244000045947 parasite Species 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 241000237858 Gastropoda Species 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000237359 Biomphalaria Species 0.000 description 6
- 241000257162 Lucilia <blowfly> Species 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 230000003071 parasitic effect Effects 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NWWZLDXOHWTTKD-UHFFFAOYSA-N 1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CN1C(=O)CC(=O)N(C)C1=S NWWZLDXOHWTTKD-UHFFFAOYSA-N 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000760148 Aspiculuris tetraptera Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000338991 Heterakis spumosa Species 0.000 description 3
- 241000257166 Lucilia cuprina Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241001480236 Strongyloides ratti Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241001221734 Trichuris muris Species 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- FVVBEWIRDMQGRS-UHFFFAOYSA-N 1-butyl-3-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCCCN1C(=O)CC(=O)N(C)C1=S FVVBEWIRDMQGRS-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical class O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000243974 Haemonchus contortus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000509416 Sarcoptes Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000869417 Trematodes Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 201000004409 schistosomiasis Diseases 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VDYWXVDWKFAUKE-UHFFFAOYSA-N 1,3,5-trichloro-2-isocyanatobenzene Chemical compound ClC1=CC(Cl)=C(N=C=O)C(Cl)=C1 VDYWXVDWKFAUKE-UHFFFAOYSA-N 0.000 description 1
- JCOMEBUHSZZAHZ-UHFFFAOYSA-N 1,3-dichloro-2-(difluoromethyl)-4-isocyanatobenzene Chemical compound FC(F)C1=C(Cl)C=CC(N=C=O)=C1Cl JCOMEBUHSZZAHZ-UHFFFAOYSA-N 0.000 description 1
- TWJPXOXVLOQYON-UHFFFAOYSA-N 1,3-dichloro-2-isocyanato-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(N=C=O)C(Cl)=C1 TWJPXOXVLOQYON-UHFFFAOYSA-N 0.000 description 1
- ZFIMUSUHAOSEIE-UHFFFAOYSA-N 1,3-diphenyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)C(=S)N1C1=CC=CC=C1 ZFIMUSUHAOSEIE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XVYUJNWODQUKTO-UHFFFAOYSA-N 1-benzyl-3-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound S=C1N(C)C(=O)CC(=O)N1CC1=CC=CC=C1 XVYUJNWODQUKTO-UHFFFAOYSA-N 0.000 description 1
- VQVBCZQTXSHJGF-UHFFFAOYSA-N 1-bromo-3-isocyanatobenzene Chemical compound BrC1=CC=CC(N=C=O)=C1 VQVBCZQTXSHJGF-UHFFFAOYSA-N 0.000 description 1
- CMENSTKBPXYTLR-UHFFFAOYSA-N 1-butan-2-yl-3-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCC(C)N1C(=O)CC(=O)N(C)C1=S CMENSTKBPXYTLR-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- NGQMCUWZGVMILT-UHFFFAOYSA-N 1-chloro-3-isocyanato-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1N=C=O NGQMCUWZGVMILT-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
- CXYBLHZWJJNVQE-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-methylbenzene Chemical compound CC1=CC(N=C=O)=CC=C1Cl CXYBLHZWJJNVQE-UHFFFAOYSA-N 0.000 description 1
- WVYJMPGPZJOOEA-UHFFFAOYSA-N 1-chloro-4-isocyanatobut-2-ene Chemical compound ClCC=CCN=C=O WVYJMPGPZJOOEA-UHFFFAOYSA-N 0.000 description 1
- MKMMDUNWJMDPHL-UHFFFAOYSA-N 1-chloro-6-isocyanatohexane Chemical compound ClCCCCCCN=C=O MKMMDUNWJMDPHL-UHFFFAOYSA-N 0.000 description 1
- FMYVTFRADSNGDN-UHFFFAOYSA-N 1-ethoxy-4-isocyanatobenzene Chemical compound CCOC1=CC=C(N=C=O)C=C1 FMYVTFRADSNGDN-UHFFFAOYSA-N 0.000 description 1
- CBUYXKSKVUBLAM-UHFFFAOYSA-N 1-ethyl-3-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCN1C(=O)CC(=O)N(C)C1=S CBUYXKSKVUBLAM-UHFFFAOYSA-N 0.000 description 1
- DSVGFKBFFICWLZ-UHFFFAOYSA-N 1-fluoro-4-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C=C1 DSVGFKBFFICWLZ-UHFFFAOYSA-N 0.000 description 1
- MTOCSSWTKSMVJJ-UHFFFAOYSA-N 1-isocyanato-1-methoxypropane Chemical compound CCC(OC)N=C=O MTOCSSWTKSMVJJ-UHFFFAOYSA-N 0.000 description 1
- SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 1
- IVMHNKJWTRJTRU-UHFFFAOYSA-N 1-isocyanato-2-methoxyethane Chemical compound COCCN=C=O IVMHNKJWTRJTRU-UHFFFAOYSA-N 0.000 description 1
- SXJYSIBLFGQAND-UHFFFAOYSA-N 1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1 SXJYSIBLFGQAND-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
- SWSXEZOUBBVKCO-UHFFFAOYSA-N 1-isocyanato-4-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1 SWSXEZOUBBVKCO-UHFFFAOYSA-N 0.000 description 1
- CHQDWIYBVHWYTG-UHFFFAOYSA-N 1-isocyanato-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(N=C=O)C=C1 CHQDWIYBVHWYTG-UHFFFAOYSA-N 0.000 description 1
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- KKASGUHLXWAKEZ-UHFFFAOYSA-N 1-isothiocyanatopropane Chemical compound CCCN=C=S KKASGUHLXWAKEZ-UHFFFAOYSA-N 0.000 description 1
- DLMPJSWFKZILOI-UHFFFAOYSA-N 1-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CN1C(=O)CC(=O)NC1=S DLMPJSWFKZILOI-UHFFFAOYSA-N 0.000 description 1
- ZZYNAGDXKYKVQH-UHFFFAOYSA-N 1-methyl-3-propan-2-yl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CC(C)N1C(=O)CC(=O)N(C)C1=S ZZYNAGDXKYKVQH-UHFFFAOYSA-N 0.000 description 1
- YPQJRSDLEFTIPE-UHFFFAOYSA-N 1-methyl-3-propyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCCN1C(=O)CC(=O)N(C)C1=S YPQJRSDLEFTIPE-UHFFFAOYSA-N 0.000 description 1
- GVROMLXQBVEPMV-UHFFFAOYSA-N 1-methyl-5-propyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCCC1C(=O)NC(=S)N(C)C1=O GVROMLXQBVEPMV-UHFFFAOYSA-N 0.000 description 1
- WUWBDQJTQTVBSQ-UHFFFAOYSA-N 1-tert-butyl-4-isocyanatobenzene Chemical compound CC(C)(C)C1=CC=C(N=C=O)C=C1 WUWBDQJTQTVBSQ-UHFFFAOYSA-N 0.000 description 1
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 description 1
- POLDSAUWRJCSOK-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C(Cl)=C1 POLDSAUWRJCSOK-UHFFFAOYSA-N 0.000 description 1
- HCWZJEXQULSHSD-UHFFFAOYSA-N 2-chloro-4-isocyanato-1-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1Cl HCWZJEXQULSHSD-UHFFFAOYSA-N 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
- WYWMWDMQTDLYRB-UHFFFAOYSA-N 2-isocyanato-5-nitro-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC([N+]([O-])=O)=CC(C(C)C)=C1N=C=O WYWMWDMQTDLYRB-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
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- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/66—Thiobarbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405732 DE2405732A1 (de) | 1974-02-07 | 1974-02-07 | Ekto- und endoparasitenmittel |
| JP1446875A JPS50107142A (enExample) | 1974-02-07 | 1975-02-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405732 DE2405732A1 (de) | 1974-02-07 | 1974-02-07 | Ekto- und endoparasitenmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2405732A1 true DE2405732A1 (de) | 1975-08-21 |
Family
ID=5906792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742405732 Pending DE2405732A1 (de) | 1974-02-07 | 1974-02-07 | Ekto- und endoparasitenmittel |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS50107142A (enExample) |
| DE (1) | DE2405732A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2601780A1 (de) * | 1976-01-20 | 1977-07-21 | Bayer Ag | Substituierte n-phenyl-n'-benzoyl- harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2936457A1 (de) * | 1978-09-12 | 1980-03-20 | Ciba Geigy Ag | Verfahren zum schuetzen von keratinischen materialien vor dem befall durch keratinfressende insekten und neue 5-phenylcarbamoyl-barbitursaeureverbindungen |
| FR2557108A1 (fr) * | 1983-12-19 | 1985-06-28 | Uniroyal Inc | 5-pyrimidinecarboxamide ou thiocarboxamide, composition pharmaceutique pour induire la regression de la leucemie et l'inhibition de la croissance des tumeurs le contenant, procede de production de 5-pyrimidinecarboxamide ou thiocarboxamide et procede pour induire la regression de la leucemie et l'inhibition de la croissance des tumeurs en l'utilisant |
| US4670441A (en) * | 1984-07-06 | 1987-06-02 | Ciba-Geigy Corporation | Thiobarbituric acid derivatives and their use as anthelminthics |
| EP0228894A3 (en) * | 1985-12-24 | 1988-06-01 | The Wellcome Foundation Limited | Pesticidal compounds |
| WO1991013623A1 (en) * | 1990-03-09 | 1991-09-19 | Memorial Hospital For Cancer And Allied Diseases | C-5 mono-substituted barbiturates in combination with therapeutic agents and uses thereof |
| WO2001081319A3 (en) * | 2000-04-24 | 2002-05-16 | Aryx Therapeutics | Ultrashort acting hypnotic barbiturates |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1483081A (en) * | 1974-09-05 | 1977-08-17 | Rothmans Of Pall Mall | Production of a stream of tobacco particles |
-
1974
- 1974-02-07 DE DE19742405732 patent/DE2405732A1/de active Pending
-
1975
- 1975-02-05 JP JP1446875A patent/JPS50107142A/ja active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2601780A1 (de) * | 1976-01-20 | 1977-07-21 | Bayer Ag | Substituierte n-phenyl-n'-benzoyl- harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2936457A1 (de) * | 1978-09-12 | 1980-03-20 | Ciba Geigy Ag | Verfahren zum schuetzen von keratinischen materialien vor dem befall durch keratinfressende insekten und neue 5-phenylcarbamoyl-barbitursaeureverbindungen |
| FR2557108A1 (fr) * | 1983-12-19 | 1985-06-28 | Uniroyal Inc | 5-pyrimidinecarboxamide ou thiocarboxamide, composition pharmaceutique pour induire la regression de la leucemie et l'inhibition de la croissance des tumeurs le contenant, procede de production de 5-pyrimidinecarboxamide ou thiocarboxamide et procede pour induire la regression de la leucemie et l'inhibition de la croissance des tumeurs en l'utilisant |
| US4634707A (en) * | 1983-12-19 | 1987-01-06 | Uniroyal Chemical Company | 5-Pyrimidinecarboxamides and treatment of leukemia and tumors therewith |
| US4670441A (en) * | 1984-07-06 | 1987-06-02 | Ciba-Geigy Corporation | Thiobarbituric acid derivatives and their use as anthelminthics |
| EP0228894A3 (en) * | 1985-12-24 | 1988-06-01 | The Wellcome Foundation Limited | Pesticidal compounds |
| US4816460A (en) * | 1985-12-24 | 1989-03-28 | Burroughs Wellcome Co. | Insecticidal dioxopyrimidine carboxyanides |
| WO1991013623A1 (en) * | 1990-03-09 | 1991-09-19 | Memorial Hospital For Cancer And Allied Diseases | C-5 mono-substituted barbiturates in combination with therapeutic agents and uses thereof |
| WO2001081319A3 (en) * | 2000-04-24 | 2002-05-16 | Aryx Therapeutics | Ultrashort acting hypnotic barbiturates |
| US6683086B2 (en) | 2000-04-24 | 2004-01-27 | Aryx Therapeutics | Ultrashort acting hypnotic barbiturates |
| US7041673B2 (en) | 2000-04-24 | 2006-05-09 | Aryx Therapeutics, Inc. | Ultrashort acting hypnotic barbiturates |
| AU2001257230B2 (en) * | 2000-04-24 | 2006-09-14 | Aryx Therapeutics | Ultrashort acting hypnotic barbiturates |
| USRE41289E1 (en) | 2000-04-24 | 2010-04-27 | Aryx Therapeutics, Inc. | Ultrashort acting hypnotic barbiturates |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50107142A (enExample) | 1975-08-23 |
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