DE1768244A1 - N-(2,2,4,4-Tetrafluor-1,3-benz-dioxanyl)-harnstoffe und Verfahren zu ihrer Herstellung - Google Patents
N-(2,2,4,4-Tetrafluor-1,3-benz-dioxanyl)-harnstoffe und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1768244A1 DE1768244A1 DE19681768244 DE1768244A DE1768244A1 DE 1768244 A1 DE1768244 A1 DE 1768244A1 DE 19681768244 DE19681768244 DE 19681768244 DE 1768244 A DE1768244 A DE 1768244A DE 1768244 A1 DE1768244 A1 DE 1768244A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrafluoro
- benzdioxanyl
- ureas
- preparation
- carbon atoms
- 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
- -1 2,2,4,4-tetrafluoro-1,3-benz-dioxanyl Chemical group 0.000 title claims description 18
- 235000013877 carbamide Nutrition 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000003672 ureas Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 241000196324 Embryophyta Species 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical compound O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 description 2
- GELYCVKPQMCBNN-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxine Chemical compound C1=CC=C2C(F)(F)OC(F)(F)OC2=C1 GELYCVKPQMCBNN-UHFFFAOYSA-N 0.000 description 2
- CEZBCWUICWDAJI-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-3-amine Chemical class C1=CC=C2OC(N)COC2=C1 CEZBCWUICWDAJI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000209200 Bromus Species 0.000 description 2
- 241000723377 Coffea Species 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000234642 Festuca Species 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
- 241000209082 Lolium Species 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 241001310793 Podium Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HFHAJBUXJRZUAZ-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-6-nitro-1,4-benzodioxine Chemical compound O1C(F)(F)C(F)(F)OC2=CC([N+](=O)[O-])=CC=C21 HFHAJBUXJRZUAZ-UHFFFAOYSA-N 0.000 description 1
- MVOUQJZLQDQNPG-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-6-nitro-1,3-benzodioxine Chemical compound FC1(OC(C2=C(O1)C=CC(=C2)[N+](=O)[O-])(F)F)F MVOUQJZLQDQNPG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LMTMXRCPYBMDJA-UHFFFAOYSA-N 3-isocyanato-2,3-dihydro-1,4-benzodioxine Chemical class C1=CC=C2OC(N=C=O)COC2=C1 LMTMXRCPYBMDJA-UHFFFAOYSA-N 0.000 description 1
- VJKVMUHKJOKUHX-UHFFFAOYSA-N 3-nitro-2,3-dihydro-1,4-benzodioxine Chemical class C1=CC=C2OC([N+](=O)[O-])COC2=C1 VJKVMUHKJOKUHX-UHFFFAOYSA-N 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 101100310622 Mus musculus Soga1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 244000274883 Urtica dioica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- WAZVTVOVPBXTOD-UHFFFAOYSA-N [2-(trichloromethyl)phenyl] carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1C(Cl)(Cl)Cl WAZVTVOVPBXTOD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 244000230030 foxtail bristlegrass Species 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768244 DE1768244A1 (de) | 1968-04-19 | 1968-04-19 | N-(2,2,4,4-Tetrafluor-1,3-benz-dioxanyl)-harnstoffe und Verfahren zu ihrer Herstellung |
| BG011612A BG15065A3 (bg) | 1968-04-19 | 1968-07-20 | Хербицидно средство |
| CH372169A CH507933A (de) | 1968-04-19 | 1969-03-12 | Verfahren zur Herstellung von N-(2,2,4,4-Tetrafluor-1,3-benzdioxanyl)-harnstoffen |
| IL31811A IL31811A (en) | 1968-04-19 | 1969-03-14 | N-(2,2,4,4-tetrafluoro-1,3-benzodioxanyl)-ureas and their preparation |
| SU1315794A SU372811A1 (ru) | 1969-03-27 | Способ получения м- | |
| BG011928A BG15678A3 (bg) | 1968-04-19 | 1969-03-27 | Хербицидно средство |
| AT335669A AT289823B (de) | 1968-04-19 | 1969-04-04 | Verfahren zur Herstellung von neuen N-(2,2,4,4-Tetrafluor-1,3-benzdioxanyl)-harnstoffen |
| AT538570A AT293784B (de) | 1968-04-19 | 1969-04-04 | Herbizides Mittel |
| US814815A US3639668A (en) | 1968-04-19 | 1969-04-09 | N-(2 2 4 4-tetrafluoro-1 3-benzodioxanyl)-ureas |
| BE731669D BE731669A (en, 2012) | 1968-04-19 | 1969-04-17 | |
| GB1986269A GB1238417A (en, 2012) | 1968-04-19 | 1969-04-18 | |
| FR6912239A FR2006559A1 (en, 2012) | 1968-04-19 | 1969-04-18 | |
| NL6906040A NL6906040A (en, 2012) | 1968-04-19 | 1969-04-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768244 DE1768244A1 (de) | 1968-04-19 | 1968-04-19 | N-(2,2,4,4-Tetrafluor-1,3-benz-dioxanyl)-harnstoffe und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768244A1 true DE1768244A1 (de) | 1971-10-14 |
Family
ID=5699661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768244 Pending DE1768244A1 (de) | 1968-04-19 | 1968-04-19 | N-(2,2,4,4-Tetrafluor-1,3-benz-dioxanyl)-harnstoffe und Verfahren zu ihrer Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3639668A (en, 2012) |
| AT (2) | AT289823B (en, 2012) |
| BE (1) | BE731669A (en, 2012) |
| BG (2) | BG15065A3 (en, 2012) |
| CH (1) | CH507933A (en, 2012) |
| DE (1) | DE1768244A1 (en, 2012) |
| FR (1) | FR2006559A1 (en, 2012) |
| GB (1) | GB1238417A (en, 2012) |
| IL (1) | IL31811A (en, 2012) |
| NL (1) | NL6906040A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0024016A1 (de) * | 1979-08-11 | 1981-02-18 | Bayer Ag | Tetrachlorphthalamidsäuren, Verfahren zu ihrer Herstellung und ihre bakterizide Verwendung |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2637947C2 (de) * | 1976-08-24 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Tetrafluor-1,3-benzodioxanyl-benzoylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| DE3023328A1 (de) * | 1980-06-21 | 1982-01-14 | Bayer Ag, 5090 Leverkusen | Substituierte benzol-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US8124630B2 (en) * | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| HK1042251B (en) * | 1999-01-13 | 2012-07-20 | Bayer Healthcare Llc | Omega-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| US7371763B2 (en) * | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| US20080108672A1 (en) * | 2002-01-11 | 2008-05-08 | Bernd Riedl | Omega-Carboxyaryl Substituted Diphenyl Ureas As Raf Kinase Inhibitors |
| ES2425739T3 (es) * | 2002-02-11 | 2013-10-17 | Bayer Healthcare Llc | Sorafenib-tosilato para el tratamiento de enfermedades caracterizadas por angiogénesis anormal |
| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| PL1626714T3 (pl) * | 2003-05-20 | 2007-12-31 | Bayer Healthcare Llc | Diarylowe pochodne mocznika do schorzeń, w których pośredniczy PDGFR |
| NZ580384A (en) | 2003-07-23 | 2011-03-31 | Bayer Pharmaceuticals Corp | 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide and metabolites for the treatment and prevention of diseases and conditions |
-
1968
- 1968-04-19 DE DE19681768244 patent/DE1768244A1/de active Pending
- 1968-07-20 BG BG011612A patent/BG15065A3/bg unknown
-
1969
- 1969-03-12 CH CH372169A patent/CH507933A/de not_active IP Right Cessation
- 1969-03-14 IL IL31811A patent/IL31811A/en unknown
- 1969-03-27 BG BG011928A patent/BG15678A3/bg unknown
- 1969-04-04 AT AT335669A patent/AT289823B/de not_active IP Right Cessation
- 1969-04-04 AT AT538570A patent/AT293784B/de active
- 1969-04-09 US US814815A patent/US3639668A/en not_active Expired - Lifetime
- 1969-04-17 BE BE731669D patent/BE731669A/xx unknown
- 1969-04-18 NL NL6906040A patent/NL6906040A/xx unknown
- 1969-04-18 GB GB1986269A patent/GB1238417A/en not_active Expired
- 1969-04-18 FR FR6912239A patent/FR2006559A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0024016A1 (de) * | 1979-08-11 | 1981-02-18 | Bayer Ag | Tetrachlorphthalamidsäuren, Verfahren zu ihrer Herstellung und ihre bakterizide Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| SU372811A3 (en, 2012) | 1973-03-01 |
| BG15678A3 (bg) | 1976-06-26 |
| IL31811A0 (en) | 1969-05-28 |
| US3639668A (en) | 1972-02-01 |
| BE731669A (en, 2012) | 1969-10-17 |
| GB1238417A (en, 2012) | 1971-07-07 |
| CH507933A (de) | 1971-05-31 |
| AT289823B (de) | 1971-05-10 |
| NL6906040A (en, 2012) | 1969-10-21 |
| FR2006559A1 (en, 2012) | 1969-12-26 |
| IL31811A (en) | 1972-03-28 |
| BG15065A3 (bg) | 1975-03-03 |
| AT293784B (de) | 1971-10-25 |
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