DE2123266A1 - 1.3.4-thiadiazolon-(5)-yl-(2)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide - Google Patents
1.3.4-thiadiazolon-(5)-yl-(2)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizideInfo
- Publication number
- DE2123266A1 DE2123266A1 DE2123266A DE2123266A DE2123266A1 DE 2123266 A1 DE2123266 A1 DE 2123266A1 DE 2123266 A DE2123266 A DE 2123266A DE 2123266 A DE2123266 A DE 2123266A DE 2123266 A1 DE2123266 A1 DE 2123266A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazolon
- tert
- butyl
- ureas
- urea
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 239000004009 herbicide Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 23
- 239000004202 carbamide Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- -1 Ligroin Chemical class 0.000 description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 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
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 241000219312 Chenopodium Species 0.000 description 2
- 241000723377 Coffea Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 235000007351 Eleusine Nutrition 0.000 description 2
- 241000209215 Eleusine Species 0.000 description 2
- 241000234642 Festuca Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LQDLGBAFSQGMGZ-UHFFFAOYSA-N 1,3,4-thiadiazole 1-oxide Chemical compound O=S1C=NN=C1 LQDLGBAFSQGMGZ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FUHHUVXHWSVKFB-UHFFFAOYSA-N 1-methyl-3-(propanoylamino)thiourea Chemical compound CCC(=O)NNC(=S)NC FUHHUVXHWSVKFB-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
- 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
- 241001049165 Caria Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 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
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- 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
- 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
- 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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 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
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000003111 delayed effect Effects 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
- 238000005516 engineering process 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 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 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
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2123266A DE2123266A1 (de) | 1971-05-11 | 1971-05-11 | 1.3.4-thiadiazolon-(5)-yl-(2)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| AU41936/72A AU4193672A (en) | 1971-05-11 | 1972-05-04 | l, 3, 4-THIADIAZOLON-(5)-YL-(2)-UREAS, PROCESS FOR THEIR PREPARATION, AND THEIR USE AS HERBICIDES |
| NL7206219A NL7206219A (cs) | 1971-05-11 | 1972-05-08 | |
| IL7239379A IL39379A (en) | 1971-05-11 | 1972-05-08 | 1-(4-tert.butyl-5-oxo-1,3,4-thiadiazolin-2-yl)-1-alkyl-ureas,their preparation and their use as herbicides |
| DD162837A DD103127A5 (cs) | 1971-05-11 | 1972-05-09 | |
| CH689072A CH575936A5 (cs) | 1971-05-11 | 1972-05-09 | |
| IT24110/72A IT961165B (it) | 1971-05-11 | 1972-05-09 | 1 3 4 tiadiazolon 5 il 2 uree procedimento per la loro prepara zione e loro impiego come erbicidi |
| GB2186572A GB1342183A (en) | 1971-05-11 | 1972-05-10 | 1,3,4-thiadiazolon-5-yl-2-ureas process for their preparation and their use as herbicides |
| ZA723204A ZA723204B (en) | 1971-05-11 | 1972-05-10 | 1,3,4-thiadiazolon-(5)-yl-(2)-ureas,process for their preparation,and their use as herbicides |
| AT408172A AT316198B (de) | 1971-05-11 | 1972-05-10 | Herbizides Mittel |
| HUBA2743A HU164565B (cs) | 1971-05-11 | 1972-05-10 | |
| FR727216690A FR2137717B1 (cs) | 1971-05-11 | 1972-05-10 | |
| DK235772AA DK131341B (da) | 1971-05-11 | 1972-05-10 | Herbicidt virksomme 4-tert.butyl-1,3,4-thiadiazolon-(5)-yl-(2)-urinstoffer. |
| BR2928/72A BR7202928D0 (pt) | 1971-05-11 | 1972-05-10 | A preparacao das mencionadas composicoes antas indesejadas com o emprego dos mesmos, e processo parprocesso para preparacao de novas 4-terciobutil-1,3,4-tiadsses compostos, processo para combater o crescimento de pliazolon-(5)-il-(2)-ureias,composicoes herbicidas a base d |
| CA141,765A CA971177A (en) | 1971-05-11 | 1972-05-10 | 1,3,4-thiadiazolon-(5)-yl-(2)-ureas, process for their preparation, and their use as herbicides |
| BE783259A BE783259A (fr) | 1971-05-11 | 1972-05-10 | Nouvelles 1.3.4-thiadiazolon-(5)-yl-(2)-urees, leur procede de preparation et leur application comme herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2123266A DE2123266A1 (de) | 1971-05-11 | 1971-05-11 | 1.3.4-thiadiazolon-(5)-yl-(2)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2123266A1 true DE2123266A1 (de) | 1973-03-01 |
Family
ID=5807518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2123266A Pending DE2123266A1 (de) | 1971-05-11 | 1971-05-11 | 1.3.4-thiadiazolon-(5)-yl-(2)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT316198B (cs) |
| AU (1) | AU4193672A (cs) |
| BE (1) | BE783259A (cs) |
| BR (1) | BR7202928D0 (cs) |
| CA (1) | CA971177A (cs) |
| CH (1) | CH575936A5 (cs) |
| DD (1) | DD103127A5 (cs) |
| DE (1) | DE2123266A1 (cs) |
| DK (1) | DK131341B (cs) |
| FR (1) | FR2137717B1 (cs) |
| GB (1) | GB1342183A (cs) |
| HU (1) | HU164565B (cs) |
| IL (1) | IL39379A (cs) |
| IT (1) | IT961165B (cs) |
| NL (1) | NL7206219A (cs) |
| ZA (1) | ZA723204B (cs) |
-
1971
- 1971-05-11 DE DE2123266A patent/DE2123266A1/de active Pending
-
1972
- 1972-05-04 AU AU41936/72A patent/AU4193672A/en not_active Expired
- 1972-05-08 IL IL7239379A patent/IL39379A/xx unknown
- 1972-05-08 NL NL7206219A patent/NL7206219A/xx unknown
- 1972-05-09 DD DD162837A patent/DD103127A5/xx unknown
- 1972-05-09 CH CH689072A patent/CH575936A5/xx not_active IP Right Cessation
- 1972-05-09 IT IT24110/72A patent/IT961165B/it active
- 1972-05-10 AT AT408172A patent/AT316198B/de not_active IP Right Cessation
- 1972-05-10 HU HUBA2743A patent/HU164565B/hu unknown
- 1972-05-10 CA CA141,765A patent/CA971177A/en not_active Expired
- 1972-05-10 BR BR2928/72A patent/BR7202928D0/pt unknown
- 1972-05-10 DK DK235772AA patent/DK131341B/da unknown
- 1972-05-10 FR FR727216690A patent/FR2137717B1/fr not_active Expired
- 1972-05-10 GB GB2186572A patent/GB1342183A/en not_active Expired
- 1972-05-10 BE BE783259A patent/BE783259A/xx unknown
- 1972-05-10 ZA ZA723204A patent/ZA723204B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL39379A (en) | 1975-07-28 |
| DK131341B (da) | 1975-06-30 |
| CH575936A5 (cs) | 1976-05-31 |
| DK131341C (cs) | 1975-11-24 |
| FR2137717A1 (cs) | 1972-12-29 |
| FR2137717B1 (cs) | 1973-07-13 |
| AU4193672A (en) | 1973-11-08 |
| DD103127A5 (cs) | 1974-01-12 |
| BR7202928D0 (pt) | 1974-01-24 |
| AT316198B (de) | 1974-06-25 |
| IT961165B (it) | 1973-12-10 |
| BE783259A (fr) | 1972-11-10 |
| IL39379A0 (en) | 1972-07-26 |
| HU164565B (cs) | 1974-03-28 |
| GB1342183A (en) | 1973-12-25 |
| NL7206219A (cs) | 1972-11-14 |
| ZA723204B (en) | 1973-02-28 |
| CA971177A (en) | 1975-07-15 |
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