DE1932297C3 - Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern - Google Patents
Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureesternInfo
- Publication number
- DE1932297C3 DE1932297C3 DE1932297A DE1932297A DE1932297C3 DE 1932297 C3 DE1932297 C3 DE 1932297C3 DE 1932297 A DE1932297 A DE 1932297A DE 1932297 A DE1932297 A DE 1932297A DE 1932297 C3 DE1932297 C3 DE 1932297C3
- Authority
- DE
- Germany
- Prior art keywords
- carbamic acid
- benzimidazole
- acid esters
- ester
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 6
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000004986 phenylenediamines Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- -1 aromatic isocyanide dichlorides Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- YHMFTWZCHPQXRM-UHFFFAOYSA-N dichloromethylidenecarbamic acid Chemical compound OC(=O)N=C(Cl)Cl YHMFTWZCHPQXRM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- FURSOPUPGJBTMU-UHFFFAOYSA-N methyl isocyanoformate Chemical compound COC(=O)[N+]#[C-] FURSOPUPGJBTMU-UHFFFAOYSA-N 0.000 description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- WQEGHHLKDKIWKM-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(N)C(N)=C1 WQEGHHLKDKIWKM-UHFFFAOYSA-N 0.000 description 1
- AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQQHTMQOMNIMAE-UHFFFAOYSA-N benzyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound N=1C2=CC=CC=C2NC=1NC(=O)OCC1=CC=CC=C1 WQQHTMQOMNIMAE-UHFFFAOYSA-N 0.000 description 1
- WOWSLHQBEQTJIQ-UHFFFAOYSA-N butyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OCCCC)=NC2=C1 WOWSLHQBEQTJIQ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BPRFCEZKJYIFJZ-UHFFFAOYSA-N ethyl isocyanoformate Chemical compound CCOC(=O)[N+]#[C-] BPRFCEZKJYIFJZ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IUROBCDXAGBTOV-UHFFFAOYSA-N methyl n-(dichloromethylidene)carbamate Chemical compound COC(=O)N=C(Cl)Cl IUROBCDXAGBTOV-UHFFFAOYSA-N 0.000 description 1
- OUQFCBDRFYTHKG-UHFFFAOYSA-N n-(dichloromethylidene)carbamoyl chloride Chemical compound ClC(Cl)=NC(Cl)=O OUQFCBDRFYTHKG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OUAAURDVPDKVAK-UHFFFAOYSA-N n-phenyl-1h-benzimidazol-2-amine Chemical class N=1C2=CC=CC=C2NC=1NC1=CC=CC=C1 OUAAURDVPDKVAK-UHFFFAOYSA-N 0.000 description 1
- QZUOHMHXPDWQDM-UHFFFAOYSA-N octyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OCCCCCCCC)=NC2=C1 QZUOHMHXPDWQDM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1932297A DE1932297C3 (de) | 1969-06-26 | 1969-06-26 | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern |
| IL7034611A IL34611A (en) | 1969-06-26 | 1970-05-27 | Process for the preparation of benzimidazole-2-carbamic acid esters |
| ZA703598A ZA703598B (en) | 1969-06-26 | 1970-05-27 | Process for the preparation of benzimidazole-2-carbamic acid esters |
| CH787070A CH529139A (de) | 1969-06-26 | 1970-05-27 | Verfahren zur Herstellung von Benzimidazol-2-carbaminsäureestern |
| CA084373A CA937935A (en) | 1969-06-26 | 1970-06-02 | Process for the preparation of benzimidazole-2-carbamic acid esters |
| BG014924A BG17319A3 (bg) | 1969-06-26 | 1970-06-12 | Метод за получаване на естери на бензими-дазол-2-карбаминова киселина |
| NL7008954A NL7008954A (xx) | 1969-06-26 | 1970-06-18 | |
| GB1256834D GB1256834A (xx) | 1969-06-26 | 1970-06-19 | |
| ES381154A ES381154A1 (es) | 1969-06-26 | 1970-06-25 | Procedimiento para la produccion de benzimidazol-2-carbama-tos. |
| BE752513D BE752513A (fr) | 1969-06-26 | 1970-06-25 | Procede de preparation d'esters d'acide benzimidazole-2- carbamique |
| SE08822/70A SE352633B (xx) | 1969-06-26 | 1970-06-25 | |
| FR7023754A FR2051372A5 (xx) | 1969-06-26 | 1970-06-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1932297A DE1932297C3 (de) | 1969-06-26 | 1969-06-26 | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1932297A1 DE1932297A1 (de) | 1971-01-07 |
| DE1932297B2 DE1932297B2 (de) | 1974-01-24 |
| DE1932297C3 true DE1932297C3 (de) | 1974-09-12 |
Family
ID=5738008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1932297A Expired DE1932297C3 (de) | 1969-06-26 | 1969-06-26 | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE752513A (xx) |
| BG (1) | BG17319A3 (xx) |
| CA (1) | CA937935A (xx) |
| CH (1) | CH529139A (xx) |
| DE (1) | DE1932297C3 (xx) |
| ES (1) | ES381154A1 (xx) |
| FR (1) | FR2051372A5 (xx) |
| GB (1) | GB1256834A (xx) |
| IL (1) | IL34611A (xx) |
| NL (1) | NL7008954A (xx) |
| SE (1) | SE352633B (xx) |
| ZA (1) | ZA703598B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2227919C2 (de) * | 1972-06-08 | 1982-12-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Benzimidazol-2-yl-carbaminsäure-methylester |
| HU169503B (xx) * | 1974-02-05 | 1976-12-28 | ||
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE3705084A1 (de) * | 1987-02-18 | 1988-09-01 | Hoechst Ag | Verfahren zur herstellung von pyrimidinen |
-
1969
- 1969-06-26 DE DE1932297A patent/DE1932297C3/de not_active Expired
-
1970
- 1970-05-27 ZA ZA703598A patent/ZA703598B/xx unknown
- 1970-05-27 CH CH787070A patent/CH529139A/de not_active IP Right Cessation
- 1970-05-27 IL IL7034611A patent/IL34611A/en unknown
- 1970-06-02 CA CA084373A patent/CA937935A/en not_active Expired
- 1970-06-12 BG BG014924A patent/BG17319A3/xx unknown
- 1970-06-18 NL NL7008954A patent/NL7008954A/xx not_active Application Discontinuation
- 1970-06-19 GB GB1256834D patent/GB1256834A/en not_active Expired
- 1970-06-25 BE BE752513D patent/BE752513A/xx unknown
- 1970-06-25 SE SE08822/70A patent/SE352633B/xx unknown
- 1970-06-25 ES ES381154A patent/ES381154A1/es not_active Expired
- 1970-06-26 FR FR7023754A patent/FR2051372A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1932297A1 (de) | 1971-01-07 |
| ZA703598B (en) | 1971-01-27 |
| BG17319A3 (bg) | 1973-07-25 |
| FR2051372A5 (xx) | 1971-04-02 |
| CH529139A (de) | 1972-10-15 |
| IL34611A0 (en) | 1970-07-19 |
| NL7008954A (xx) | 1970-12-29 |
| GB1256834A (xx) | 1971-12-15 |
| IL34611A (en) | 1973-01-30 |
| SE352633B (xx) | 1973-01-08 |
| DE1932297B2 (de) | 1974-01-24 |
| CA937935A (en) | 1973-12-04 |
| BE752513A (fr) | 1970-12-28 |
| ES381154A1 (es) | 1972-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |