DE1567151C3 - Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel - Google Patents
Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide MittelInfo
- Publication number
- DE1567151C3 DE1567151C3 DE1567151A DE1567151A DE1567151C3 DE 1567151 C3 DE1567151 C3 DE 1567151C3 DE 1567151 A DE1567151 A DE 1567151A DE 1567151 A DE1567151 A DE 1567151A DE 1567151 C3 DE1567151 C3 DE 1567151C3
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- carbamate
- carbamoyloxy
- ethyl
- methyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title description 17
- 230000002363 herbicidal effect Effects 0.000 title description 6
- 238000000034 method Methods 0.000 title description 5
- 239000000203 mixture Substances 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 36
- -1 3 - (N '- phenylcarbamoyloxy) phenyl Chemical group 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 244000042664 Matricaria chamomilla Species 0.000 description 5
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 5
- 240000003705 Senecio vulgaris Species 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- 244000056139 Brassica cretica Species 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- DXDDOFMELPWPMI-UHFFFAOYSA-N ethyl n-hydroxy-n-phenylcarbamate Chemical class CCOC(=O)N(O)C1=CC=CC=C1 DXDDOFMELPWPMI-UHFFFAOYSA-N 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 235000008427 Brassica arvensis Nutrition 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- 244000214240 Galinsoga parviflora Species 0.000 description 2
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVEFZZKZBYQFPP-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] n-(3-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 MVEFZZKZBYQFPP-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 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
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000010871 livestock manure Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- KCLZXXMMEDEBMF-UHFFFAOYSA-N ethyl n-(3-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(O)=C1 KCLZXXMMEDEBMF-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Connector Housings Or Holding Contact Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC036854 | 1965-04-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1567151A1 DE1567151A1 (de) | 1969-07-03 |
| DE1567151B2 DE1567151B2 (de) | 1973-07-19 |
| DE1567151C3 true DE1567151C3 (de) | 1974-02-21 |
Family
ID=7434030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1567151A Expired DE1567151C3 (de) | 1965-04-09 | 1965-04-09 | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3692820A (en, 2012) |
| BE (1) | BE679283A (en, 2012) |
| CH (1) | CH478100A (en, 2012) |
| DE (1) | DE1567151C3 (en, 2012) |
| DK (1) | DK107793C (en, 2012) |
| FI (1) | FI40592B (en, 2012) |
| FR (1) | FR1475241A (en, 2012) |
| GB (1) | GB1127050A (en, 2012) |
| IL (1) | IL25420A (en, 2012) |
| LU (1) | LU50853A1 (en, 2012) |
| MY (1) | MY6900350A (en, 2012) |
| NL (1) | NL146798B (en, 2012) |
| NO (1) | NO115194B (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2732848A1 (de) | 1977-07-18 | 1979-02-08 | Schering Ag | Diurethane, herbizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| DE2843691A1 (de) | 1978-10-04 | 1980-04-24 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| DE2901658A1 (de) | 1979-01-15 | 1980-07-24 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| US4317674A (en) | 1976-11-03 | 1982-03-02 | Schering Ag | Diurethanes, process for making the same and selective herbicide composition containing same |
| DE3338760A1 (de) | 1983-10-21 | 1985-05-02 | Schering AG, 1000 Berlin und 4709 Bergkamen | 2-phenoxypropionsaeurederivate von pentiten vom typ heterocyclischer aether, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider wirkung |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450745A (en) * | 1966-01-18 | 1969-06-17 | Union Carbide Corp | Alkyl and aryl 4-(methylcarbamoyloxy) carbanilates |
| DE1567164C2 (de) * | 1966-09-10 | 1985-03-07 | Schering AG, 1000 Berlin und 4709 Bergkamen | Herbizide Mittel auf Basis von N-Carbamoyloxyphenyl-Carbamaten |
| US3898075A (en) * | 1970-01-20 | 1975-08-05 | Freund Heinz Eberhard | Stabilized liquid compositions |
| DE2020729C2 (de) * | 1970-04-23 | 1983-04-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Herbizide Mittel auf Basis von N-(3-(N'-Aryl-carbamoyloxy)-phenyl)-carbamaten |
| US4076518A (en) * | 1970-08-20 | 1978-02-28 | Schering Aktiengesellschaft | Substituted phenyl thiocarbamates with herbicidal action and method for their production |
| US3904396A (en) * | 1971-03-23 | 1975-09-09 | Schering Ag | Herbicidal mixture of several carbamoyloxyphenylcarbamates |
| DE2121958C3 (de) * | 1971-04-27 | 1981-05-27 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Herbizide Mittel auf Basis von Carbamoyloxyphenylcarbamat-Gemischen |
| DE2217698A1 (de) * | 1972-04-13 | 1973-10-18 | Basf Ag | Herbizid |
| US3938984A (en) * | 1972-04-13 | 1976-02-17 | Basf Aktiengesellschaft | Herbicide |
| US3933465A (en) * | 1972-04-13 | 1976-01-20 | Badische Anilin- & Soda-Fabrik Aktiengesellschaft | Herbicide mixtures of 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate |
| US3935001A (en) * | 1972-04-13 | 1976-01-27 | Basf Aktiengesellschaft | Herbicide mixtures of uracil, a carbamate and a pyridazone |
| DE2413933A1 (de) * | 1974-03-20 | 1975-09-25 | Schering Ag | Diurethane mit selektiver herbizider wirkung |
| DE2608473A1 (de) * | 1976-02-27 | 1977-09-01 | Schering Ag | N-methylcarbanilsaeure- eckige klammer auf 3-(aethoxycarbonylamino)-phenyl eckige klammer zu -ester als baumwollherbizides mittel |
| GR66157B (en, 2012) * | 1976-08-28 | 1981-01-20 | Basf Ag | |
| DE2651526A1 (de) * | 1976-11-09 | 1978-05-18 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
| DE2819748C2 (de) * | 1978-05-02 | 1986-07-31 | Schering AG, 1000 Berlin und 4709 Bergkamen | N-Äthylcarbanilsäure-(3-methoxycarbonylamino)-phenylester, Verfahren zur Herstellung dieser Verbindung sowie diese enthaltendes selektives herbizides Mittel |
| DE3024583A1 (de) * | 1980-06-28 | 1982-02-04 | Basf Ag, 6700 Ludwigshafen | Carbonylaminourethane und diese enthaltende herbizide und fungizide |
| US4381195A (en) * | 1981-04-20 | 1983-04-26 | Stauffer Chemical Company | N-Methylcarbamoyloxy anilides as herbicide extenders |
| US4381196A (en) * | 1981-04-20 | 1983-04-26 | Stauffer Chemical Company | O-(Substituted phenyl) N-methylcarbamates as herbicide extenders |
| AT374452B (de) * | 1982-08-30 | 1984-04-25 | Rhone Poulenc Agrochimie | Verfahren zur herstellung von phenmedipham |
| ES8604495A1 (es) * | 1983-09-20 | 1986-02-01 | Koege Kemisk Vaerk | Un procedimiento para preparar fenil-carbamatos sustituidos |
| CZ280059B6 (cs) * | 1984-02-29 | 1995-10-18 | Schering Aktiengesellschaft | Stabilizovaný kapalný herbicidní prostředek a způsob hubení plevelných rostlin |
| US5246912A (en) * | 1984-02-29 | 1993-09-21 | Berol Nobel (Suisse) S.A. | Herbicidal compositions of phenmedipham and desmedipham |
| US5651975A (en) * | 1991-09-27 | 1997-07-29 | Harju-Jeanty; Pontus | Method for the preparation of herbicidal granular products comprising two separate phases |
| FI952546A0 (fi) * | 1995-05-24 | 1995-05-24 | Kemira Agro Oy | Bekaempningsmedelspreparat och foerfaranden foer framstaellning av desamma |
| DE19605786A1 (de) | 1996-02-16 | 1997-08-21 | Hoechst Schering Agrevo Gmbh | Ölsuspensionskonzentrate |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| ES2650673T5 (es) | 2010-10-15 | 2022-03-10 | Bayer Cropscience Ag | Uso de herbicidas inhibidores de ALS para el control de vegetación indeseada en plantas Beta vulgaris tolerantes a herbicidas inhibidores de ALS |
| EA029716B1 (ru) | 2011-05-04 | 2018-05-31 | Байер Интеллектчуал Проперти Гмбх | Применение гербицидов ингибиторов als для борьбы с нежелательными растениями среди растений brassica, таких как b. napus, толерантных к гербицидам ингибиторов als |
| PL2931034T5 (pl) | 2012-12-13 | 2022-09-12 | Bayer Cropscience Ag | Zastosowanie herbicydów inhibitorów ALS do kontroli niepożądanej roślinności w roślinach Beta vulgaris z tolerancją herbicydów inhibitorów ALS |
| CN118201483A (zh) | 2021-10-15 | 2024-06-14 | 科沃施种子欧洲股份两合公司 | ALS抑制剂除草剂耐受的甜菜(Beta Vulgaris)突变体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3404975A (en) * | 1964-12-18 | 1968-10-08 | Fmc Corp | m-(carbamoyloxy)-carbanilates as herbicides |
-
1965
- 1965-04-09 DE DE1567151A patent/DE1567151C3/de not_active Expired
-
1966
- 1966-03-10 FI FI0610/66A patent/FI40592B/fi active
- 1966-03-18 IL IL25420A patent/IL25420A/xx unknown
- 1966-03-21 DK DK146466AA patent/DK107793C/da active
- 1966-04-01 CH CH481766A patent/CH478100A/de not_active IP Right Cessation
- 1966-04-01 NL NL666604363A patent/NL146798B/xx not_active IP Right Cessation
- 1966-04-01 GB GB14543/66A patent/GB1127050A/en not_active Expired
- 1966-04-05 NO NO162459A patent/NO115194B/no unknown
- 1966-04-07 FR FR56871A patent/FR1475241A/fr not_active Expired
- 1966-04-07 LU LU50853A patent/LU50853A1/xx unknown
- 1966-04-08 BE BE679283D patent/BE679283A/fr not_active IP Right Cessation
-
1969
- 1969-09-25 US US861198A patent/US3692820A/en not_active Expired - Lifetime
- 1969-12-31 MY MY1969350A patent/MY6900350A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4317674A (en) | 1976-11-03 | 1982-03-02 | Schering Ag | Diurethanes, process for making the same and selective herbicide composition containing same |
| DE2732848A1 (de) | 1977-07-18 | 1979-02-08 | Schering Ag | Diurethane, herbizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| DE2843691A1 (de) | 1978-10-04 | 1980-04-24 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| DE2901658A1 (de) | 1979-01-15 | 1980-07-24 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| DE3338760A1 (de) | 1983-10-21 | 1985-05-02 | Schering AG, 1000 Berlin und 4709 Bergkamen | 2-phenoxypropionsaeurederivate von pentiten vom typ heterocyclischer aether, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider wirkung |
Also Published As
| Publication number | Publication date |
|---|---|
| CH478100A (de) | 1969-09-15 |
| US3692820A (en) | 1972-09-19 |
| BE679283A (en, 2012) | 1966-10-10 |
| MY6900350A (en) | 1969-12-31 |
| NL6604363A (en, 2012) | 1966-10-10 |
| DK107793C (da) | 1967-07-03 |
| NL146798B (nl) | 1975-08-15 |
| GB1127050A (en) | 1968-09-11 |
| FR1475241A (fr) | 1967-03-31 |
| DE1567151B2 (de) | 1973-07-19 |
| FI40592B (en, 2012) | 1968-11-30 |
| IL25420A (en) | 1969-11-12 |
| DE1567151A1 (de) | 1969-07-03 |
| NO115194B (en, 2012) | 1968-08-26 |
| LU50853A1 (en, 2012) | 1966-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |