DE1770467A1 - 1,3,4-Thiadiazolyl-harnstoffe - Google Patents
1,3,4-Thiadiazolyl-harnstoffeInfo
- Publication number
- DE1770467A1 DE1770467A1 DE19681770467 DE1770467A DE1770467A1 DE 1770467 A1 DE1770467 A1 DE 1770467A1 DE 19681770467 DE19681770467 DE 19681770467 DE 1770467 A DE1770467 A DE 1770467A DE 1770467 A1 DE1770467 A1 DE 1770467A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- ureas
- thiadiazoly
- meaning given
- 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
- 235000013877 carbamide Nutrition 0.000 title claims description 11
- -1 1,3,4-thiadiazolyl ureas Chemical class 0.000 title claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 150000003672 ureas Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000209200 Bromus Species 0.000 description 2
- 241000723377 Coffea Species 0.000 description 2
- 229920000742 Cotton Polymers 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
- 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
- 241000209094 Oryza Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-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 group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001049165 Caria Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 235000009438 Gossypium Nutrition 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
- 241000219833 Phaseolus Species 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
- 241000746983 Phleum pratense Species 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 241000209051 Saccharum Species 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
- 244000062793 Sorghum vulgare Species 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
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides 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
- 239000002585 base 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 Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 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
- 230000017525 heat dissipation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000036435 stunted growth Effects 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770467 DE1770467A1 (de) | 1968-05-22 | 1968-05-22 | 1,3,4-Thiadiazolyl-harnstoffe |
| CH591369A CH512181A (de) | 1968-05-22 | 1969-04-17 | Herbizides Mittel |
| IL32047A IL32047A0 (en) | 1968-05-22 | 1969-04-20 | 1,3,4-thiadiazolyl ureas,their preparation and use for destroying weeds |
| RO59913A RO55667A (enExample) | 1968-05-22 | 1969-05-07 | |
| NL6906983A NL6906983A (enExample) | 1968-05-22 | 1969-05-07 | |
| BG012219A BG16162A3 (bg) | 1968-05-22 | 1969-05-09 | Хербицидно средство |
| CS3328A CS151513B2 (enExample) | 1968-05-22 | 1969-05-12 | |
| GB24853/69A GB1276925A (en) | 1968-05-22 | 1969-05-15 | 0,3,4-thiadiazolyl ureas |
| YU01234/69A YU123469A (en) | 1968-05-22 | 1969-05-19 | Process for preparing novel 1,3,4-thiadiazolyl-carbamates |
| AT482969A AT290199B (de) | 1968-05-22 | 1969-05-21 | Herbizides Mittel |
| BE733367D BE733367A (enExample) | 1968-05-22 | 1969-05-21 | |
| ES367478A ES367478A1 (es) | 1968-05-22 | 1969-05-21 | Procedimiento para la obtencion de un medio herbicida a ba-se de 1,3,4-tiadiazolil-ureas. |
| FI691538A FI52723C (fi) | 1968-05-22 | 1969-05-21 | Rikkaruohomyrkkyinä vaikuttavat 1,3,4-tiadiatsolyyli-virtsa-aineet. |
| FR6916781A FR2009152A1 (enExample) | 1968-05-22 | 1969-05-22 | |
| MY285/73A MY7300285A (en) | 1968-05-22 | 1973-12-30 | 1,3,4-thiadiazolyl ureas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770467 DE1770467A1 (de) | 1968-05-22 | 1968-05-22 | 1,3,4-Thiadiazolyl-harnstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770467A1 true DE1770467A1 (de) | 1971-11-04 |
Family
ID=5700523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770467 Pending DE1770467A1 (de) | 1968-05-22 | 1968-05-22 | 1,3,4-Thiadiazolyl-harnstoffe |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT290199B (enExample) |
| BE (1) | BE733367A (enExample) |
| BG (1) | BG16162A3 (enExample) |
| CH (1) | CH512181A (enExample) |
| CS (1) | CS151513B2 (enExample) |
| DE (1) | DE1770467A1 (enExample) |
| ES (1) | ES367478A1 (enExample) |
| FI (1) | FI52723C (enExample) |
| FR (1) | FR2009152A1 (enExample) |
| GB (1) | GB1276925A (enExample) |
| IL (1) | IL32047A0 (enExample) |
| MY (1) | MY7300285A (enExample) |
| NL (1) | NL6906983A (enExample) |
| RO (1) | RO55667A (enExample) |
| YU (1) | YU123469A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2330453A1 (de) * | 1973-06-15 | 1975-01-09 | Velsicol Chemical Corp | Dialkylacetale von heterocyclischem ureidoacetaldehyd und deren wasserloesliche salze |
| US4174398A (en) * | 1977-03-23 | 1979-11-13 | Bayer Aktiengesellschaft | Combating fungi with 1-alkyl-1-(1,3,4-thiadiazol-2-yl)-3-phenyl-ureas |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1427087A (enExample) * | 1972-08-14 | 1976-03-03 | ||
| GB1561636A (en) * | 1975-11-07 | 1980-02-27 | Lilly Industries Ltd | Herbicidal combinations |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
| US4338449A (en) | 1981-06-15 | 1982-07-06 | Eli Lilly And Company | Herbicidal thiadiazolines |
| US4346225A (en) | 1981-06-15 | 1982-08-24 | Eli Lilly And Company | Herbicidal 2-methylamino thiadiazolines |
-
1968
- 1968-05-22 DE DE19681770467 patent/DE1770467A1/de active Pending
-
1969
- 1969-04-17 CH CH591369A patent/CH512181A/de not_active IP Right Cessation
- 1969-04-20 IL IL32047A patent/IL32047A0/xx unknown
- 1969-05-07 NL NL6906983A patent/NL6906983A/xx unknown
- 1969-05-07 RO RO59913A patent/RO55667A/ro unknown
- 1969-05-09 BG BG012219A patent/BG16162A3/bg unknown
- 1969-05-12 CS CS3328A patent/CS151513B2/cs unknown
- 1969-05-15 GB GB24853/69A patent/GB1276925A/en not_active Expired
- 1969-05-19 YU YU01234/69A patent/YU123469A/xx unknown
- 1969-05-21 FI FI691538A patent/FI52723C/fi active
- 1969-05-21 ES ES367478A patent/ES367478A1/es not_active Expired
- 1969-05-21 BE BE733367D patent/BE733367A/xx unknown
- 1969-05-21 AT AT482969A patent/AT290199B/de not_active IP Right Cessation
- 1969-05-22 FR FR6916781A patent/FR2009152A1/fr not_active Withdrawn
-
1973
- 1973-12-30 MY MY285/73A patent/MY7300285A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2330453A1 (de) * | 1973-06-15 | 1975-01-09 | Velsicol Chemical Corp | Dialkylacetale von heterocyclischem ureidoacetaldehyd und deren wasserloesliche salze |
| US4174398A (en) * | 1977-03-23 | 1979-11-13 | Bayer Aktiengesellschaft | Combating fungi with 1-alkyl-1-(1,3,4-thiadiazol-2-yl)-3-phenyl-ureas |
Also Published As
| Publication number | Publication date |
|---|---|
| BG16162A3 (bg) | 1972-07-20 |
| FI52723B (enExample) | 1977-08-01 |
| MY7300285A (en) | 1973-12-31 |
| CH512181A (de) | 1971-09-15 |
| FI52723C (fi) | 1977-11-10 |
| NL6906983A (enExample) | 1969-11-25 |
| BE733367A (enExample) | 1969-11-21 |
| ES367478A1 (es) | 1971-04-01 |
| RO55667A (enExample) | 1973-11-20 |
| CS151513B2 (enExample) | 1973-10-19 |
| IL32047A0 (en) | 1969-06-25 |
| AT290199B (de) | 1971-05-25 |
| GB1276925A (en) | 1972-06-07 |
| YU123469A (en) | 1978-12-31 |
| FR2009152A1 (enExample) | 1970-01-30 |
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