CH618584A5 - Carbamate-containing herbicide - Google Patents
Carbamate-containing herbicide Download PDFInfo
- Publication number
- CH618584A5 CH618584A5 CH912775A CH912775A CH618584A5 CH 618584 A5 CH618584 A5 CH 618584A5 CH 912775 A CH912775 A CH 912775A CH 912775 A CH912775 A CH 912775A CH 618584 A5 CH618584 A5 CH 618584A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbamic acid
- ester
- alkyl
- phenyl
- general formula
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 2
- 230000002363 herbicidal effect Effects 0.000 title description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- KCLZXXMMEDEBMF-UHFFFAOYSA-N ethyl n-(3-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(O)=C1 KCLZXXMMEDEBMF-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- WQEBQCOHDAWORA-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-phenylcarbamate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC(=O)NC1=CC=CC=C1 WQEBQCOHDAWORA-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- GMEYMTDUKUVNKW-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-(3-methylphenyl)carbamate Chemical compound CC1=CC=CC(NC(=O)OC=2C(=C(Cl)C(Cl)=C(Cl)C=2Cl)Cl)=C1 GMEYMTDUKUVNKW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- -1 monochlorophenyl Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 150000001412 amines Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- SIZKDIQMNFWPBD-UHFFFAOYSA-N hydroxy(phenyl)carbamic acid Chemical class OC(=O)N(O)C1=CC=CC=C1 SIZKDIQMNFWPBD-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WFTJCZOBXDNNOZ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) N-cyclohexylcarbamate Chemical compound ClC1=C(C(=C(C(=C1OC(NC1CCCCC1)=O)Cl)Cl)Cl)Cl WFTJCZOBXDNNOZ-UHFFFAOYSA-N 0.000 description 1
- GIPHFLWHNAYKHC-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-(4-chlorophenyl)carbamate Chemical compound C1=CC(Cl)=CC=C1NC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl GIPHFLWHNAYKHC-UHFFFAOYSA-N 0.000 description 1
- FTCSFJOFZGYXFX-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl FTCSFJOFZGYXFX-UHFFFAOYSA-N 0.000 description 1
- LCEYJTJDZROKOK-UHFFFAOYSA-N (3-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(O)=C1 LCEYJTJDZROKOK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- 230000006179 O-acylation Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000002252 carbamoylating effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013078 crystal Substances 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 239000012452 mother liquor Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1490A HU170115B (sv) | 1974-07-12 | 1974-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618584A5 true CH618584A5 (en) | 1980-08-15 |
Family
ID=10994526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH912775A CH618584A5 (en) | 1974-07-12 | 1975-07-11 | Carbamate-containing herbicide |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5132542A (sv) |
| AR (1) | AR222621A1 (sv) |
| BE (1) | BE831262A (sv) |
| CA (1) | CA1064048A (sv) |
| CH (1) | CH618584A5 (sv) |
| CS (1) | CS194721B2 (sv) |
| DD (1) | DD121512A2 (sv) |
| DE (1) | DE2530521B2 (sv) |
| DK (1) | DK139027B (sv) |
| EG (1) | EG11800A (sv) |
| ES (1) | ES439294A1 (sv) |
| FI (1) | FI61873C (sv) |
| FR (1) | FR2277816A1 (sv) |
| GB (1) | GB1479250A (sv) |
| HU (1) | HU170115B (sv) |
| IL (1) | IL47668A (sv) |
| IN (1) | IN140842B (sv) |
| MX (1) | MX3678E (sv) |
| NL (1) | NL7508245A (sv) |
| NO (1) | NO752505L (sv) |
| PL (1) | PL104534B1 (sv) |
| SE (1) | SE420088B (sv) |
| SU (1) | SU886738A3 (sv) |
-
1974
- 1974-07-12 HU HUCI1490A patent/HU170115B/hu unknown
-
1975
- 1975-07-08 IL IL47668A patent/IL47668A/xx unknown
- 1975-07-09 EG EG401/75A patent/EG11800A/xx active
- 1975-07-09 DE DE2530521A patent/DE2530521B2/de not_active Ceased
- 1975-07-10 IN IN1349/CAL/1975A patent/IN140842B/en unknown
- 1975-07-10 FR FR7521688A patent/FR2277816A1/fr active Granted
- 1975-07-10 NL NL7508245A patent/NL7508245A/xx not_active Application Discontinuation
- 1975-07-10 FI FI752008A patent/FI61873C/fi not_active IP Right Cessation
- 1975-07-10 ES ES439294A patent/ES439294A1/es not_active Expired
- 1975-07-10 SE SE7507951A patent/SE420088B/sv unknown
- 1975-07-11 JP JP50084566A patent/JPS5132542A/ja active Pending
- 1975-07-11 DD DD187258A patent/DD121512A2/xx unknown
- 1975-07-11 BE BE158200A patent/BE831262A/xx not_active IP Right Cessation
- 1975-07-11 GB GB29290/75A patent/GB1479250A/en not_active Expired
- 1975-07-11 CS CS754932A patent/CS194721B2/cs unknown
- 1975-07-11 NO NO752505A patent/NO752505L/no unknown
- 1975-07-11 SU SU752153655A patent/SU886738A3/ru active
- 1975-07-11 CH CH912775A patent/CH618584A5/de not_active IP Right Cessation
- 1975-07-11 AR AR259528A patent/AR222621A1/es active
- 1975-07-11 DK DK318175AA patent/DK139027B/da not_active IP Right Cessation
- 1975-07-11 CA CA231,284A patent/CA1064048A/en not_active Expired
- 1975-07-12 PL PL1975182043A patent/PL104534B1/pl unknown
- 1975-07-14 MX MX75100304U patent/MX3678E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL47668A (en) | 1978-03-10 |
| FI752008A (sv) | 1976-01-13 |
| PL104534B1 (pl) | 1979-08-31 |
| HU170115B (sv) | 1977-04-28 |
| FI61873C (fi) | 1982-10-11 |
| SU886738A3 (ru) | 1981-11-30 |
| DE2530521A1 (de) | 1976-01-29 |
| SE7507951L (sv) | 1976-01-13 |
| NL7508245A (nl) | 1976-01-14 |
| FR2277816A1 (fr) | 1976-02-06 |
| FR2277816B1 (sv) | 1982-07-30 |
| BE831262A (fr) | 1975-11-03 |
| DE2530521B2 (de) | 1978-03-16 |
| IN140842B (sv) | 1976-12-25 |
| FI61873B (fi) | 1982-06-30 |
| EG11800A (en) | 1979-03-31 |
| DD121512A2 (sv) | 1976-08-05 |
| AR222621A1 (es) | 1981-06-15 |
| JPS5132542A (en) | 1976-03-19 |
| NO752505L (sv) | 1976-01-13 |
| IL47668A0 (en) | 1975-10-15 |
| DK318175A (sv) | 1976-01-13 |
| GB1479250A (en) | 1977-07-06 |
| SE420088B (sv) | 1981-09-14 |
| AU8296275A (en) | 1977-01-13 |
| ES439294A1 (es) | 1977-03-01 |
| CA1064048A (en) | 1979-10-09 |
| MX3678E (es) | 1981-04-23 |
| DK139027C (sv) | 1979-05-07 |
| CS194721B2 (en) | 1979-12-31 |
| DK139027B (da) | 1978-12-04 |
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