DE1020971B - Verfahren zur Herstellung von Carbaminsäureestern des 2,4,5-Trichlorphenols - Google Patents
Verfahren zur Herstellung von Carbaminsäureestern des 2,4,5-TrichlorphenolsInfo
- Publication number
- DE1020971B DE1020971B DENDAT1020971D DE1020971DA DE1020971B DE 1020971 B DE1020971 B DE 1020971B DE NDAT1020971 D DENDAT1020971 D DE NDAT1020971D DE 1020971D A DE1020971D A DE 1020971DA DE 1020971 B DE1020971 B DE 1020971B
- Authority
- DE
- Germany
- Prior art keywords
- trichlorophenol
- substituted
- carbamic acid
- monoaryl
- acid
- 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
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 title claims description 13
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 7
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- -1 2,4,5-trichlorophenyl cyanoformate Chemical compound 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001714 carbamic acid halides Chemical class 0.000 claims 1
- 229910052801 chlorine Chemical group 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000001408 fungistatic effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 210000000795 conjunctiva Anatomy 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- JMYRIUZLEQJWNF-UHFFFAOYSA-N (2,4,5-trichlorophenyl) carbamate Chemical class NC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl JMYRIUZLEQJWNF-UHFFFAOYSA-N 0.000 description 1
- RHNSSYGTJAAVCR-UHFFFAOYSA-N (4-methylphenyl)carbamic acid Chemical compound CC1=CC=C(NC(O)=O)C=C1 RHNSSYGTJAAVCR-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
- 241000223600 Alternaria Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- 241000489964 Fusicladium Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000007711 Peperomia pellucida Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 150000001715 carbamic acids Chemical class 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 231100000017 mucous membrane irritation Toxicity 0.000 description 1
- YSBUANSGDLZTKV-UHFFFAOYSA-N n-phenylcarbamoyl chloride Chemical compound ClC(=O)NC1=CC=CC=C1 YSBUANSGDLZTKV-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE359562X | 1956-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1020971B true DE1020971B (de) | 1957-12-19 |
Family
ID=6291219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1020971D Pending DE1020971B (de) | 1956-12-04 | Verfahren zur Herstellung von Carbaminsäureestern des 2,4,5-Trichlorphenols |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE562631A (enrdf_load_stackoverflow) |
| CH (1) | CH359562A (enrdf_load_stackoverflow) |
| DE (1) | DE1020971B (enrdf_load_stackoverflow) |
| GB (1) | GB834358A (enrdf_load_stackoverflow) |
| NL (2) | NL222578A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1166180B (de) * | 1960-06-07 | 1964-03-26 | Bayer Ag | Verfahren zur Herstellung von Carbaminsaeureestern |
| FR2614300A1 (fr) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | Nouveau procede d'obtention de carbamates actives. |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2138804A (en) * | 1983-04-27 | 1984-10-31 | Sumitomo Chemical Co | Fungicidal N-phenylcarbamates |
-
0
- NL NL99972D patent/NL99972C/xx active
- NL NL222578D patent/NL222578A/xx unknown
- BE BE562631D patent/BE562631A/xx unknown
- DE DENDAT1020971D patent/DE1020971B/de active Pending
-
1957
- 1957-11-21 CH CH359562D patent/CH359562A/de unknown
- 1957-12-02 GB GB37504/57A patent/GB834358A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1166180B (de) * | 1960-06-07 | 1964-03-26 | Bayer Ag | Verfahren zur Herstellung von Carbaminsaeureestern |
| FR2614300A1 (fr) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | Nouveau procede d'obtention de carbamates actives. |
| US4883903A (en) * | 1987-04-22 | 1989-11-28 | Sanofi | Novel procedure for the preparation of activated nitrosocarbamates |
Also Published As
| Publication number | Publication date |
|---|---|
| NL222578A (enrdf_load_stackoverflow) | |
| NL99972C (enrdf_load_stackoverflow) | |
| CH359562A (de) | 1962-01-15 |
| GB834358A (en) | 1960-05-04 |
| BE562631A (enrdf_load_stackoverflow) |
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