FR2510994A1 - Procede de preparation de l'herbicide phenmedipham - Google Patents
Procede de preparation de l'herbicide phenmedipham Download PDFInfo
- Publication number
- FR2510994A1 FR2510994A1 FR8115577A FR8115577A FR2510994A1 FR 2510994 A1 FR2510994 A1 FR 2510994A1 FR 8115577 A FR8115577 A FR 8115577A FR 8115577 A FR8115577 A FR 8115577A FR 2510994 A1 FR2510994 A1 FR 2510994A1
- Authority
- FR
- France
- Prior art keywords
- reaction
- metatolyl
- isocyanate
- phosgene
- phenmedipham
- 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.)
- Granted
Links
- 239000005594 Phenmedipham Substances 0.000 title claims abstract description 17
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000002363 herbicidal effect Effects 0.000 title abstract description 3
- 239000004009 herbicide Substances 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 17
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims abstract description 14
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 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 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QUDZAFKCASPJLX-UHFFFAOYSA-N 2-aminophenol;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1O QUDZAFKCASPJLX-UHFFFAOYSA-N 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- -1 carbomethoxyaminophenyl ester Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- KZTKVXKUFOPSLC-UHFFFAOYSA-N ethyl n-(2-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC=C1O KZTKVXKUFOPSLC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- SIZKDIQMNFWPBD-UHFFFAOYSA-N hydroxy(phenyl)carbamic acid Chemical compound OC(=O)N(O)C1=CC=CC=C1 SIZKDIQMNFWPBD-UHFFFAOYSA-N 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
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 description 1
- 235000009991 pite Nutrition 0.000 description 1
- 244000293655 pite Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| FR8115577A FR2510994A1 (fr) | 1981-08-10 | 1981-08-10 | Procede de preparation de l'herbicide phenmedipham |
| IT8222593A IT1157312B (it) | 1981-08-10 | 1982-07-27 | Procedimento di preparazione dell'erbicida phenmedipham |
| IL66464A IL66464A0 (en) | 1981-08-10 | 1982-08-04 | Process for the preparation of phenmedipham |
| LU84320A LU84320A1 (fr) | 1981-08-10 | 1982-08-05 | Procede de preparation de l'herbicide phenmedipham |
| NL8203123A NL8203123A (nl) | 1981-08-10 | 1982-08-06 | Werkwijze ter bereiding van phenmedipham. |
| JP57137150A JPS58185551A (ja) | 1981-08-10 | 1982-08-06 | 除草剤フエンメジフアムの製造方法 |
| BE0/208774A BE894062A (fr) | 1981-08-10 | 1982-08-09 | Procede de preparation de l'herbicide phenmedipham |
| DE19823229589 DE3229589A1 (de) | 1981-08-10 | 1982-08-09 | Verfahren zur herstellung von phenmedipham |
| DK356582A DK356582A (da) | 1981-08-10 | 1982-08-09 | Fremgangsmaade til fremstilling af herbicidet phenmedipham |
| ES514848A ES514848A0 (es) | 1981-08-10 | 1982-08-09 | "procedimiento para preparar el herbicida fenmedifam". |
| GB08222879A GB2104519A (en) | 1981-08-10 | 1982-08-09 | Process for the preparation of the herbicide phenmedipham |
| DD82242354A DD202232A5 (de) | 1981-08-10 | 1982-08-09 | Waessrige konzentrierte suspensionen auf der basis von neburon und ihre herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8115577A FR2510994A1 (fr) | 1981-08-10 | 1981-08-10 | Procede de preparation de l'herbicide phenmedipham |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2510994A1 true FR2510994A1 (fr) | 1983-02-11 |
| FR2510994B1 FR2510994B1 (enExample) | 1984-07-13 |
Family
ID=9261401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8115577A Granted FR2510994A1 (fr) | 1981-08-10 | 1981-08-10 | Procede de preparation de l'herbicide phenmedipham |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS58185551A (enExample) |
| BE (1) | BE894062A (enExample) |
| DD (1) | DD202232A5 (enExample) |
| DE (1) | DE3229589A1 (enExample) |
| DK (1) | DK356582A (enExample) |
| ES (1) | ES514848A0 (enExample) |
| FR (1) | FR2510994A1 (enExample) |
| GB (1) | GB2104519A (enExample) |
| IL (1) | IL66464A0 (enExample) |
| IT (1) | IT1157312B (enExample) |
| LU (1) | LU84320A1 (enExample) |
| NL (1) | NL8203123A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8604495A1 (es) * | 1983-09-20 | 1986-02-01 | Koege Kemisk Vaerk | Un procedimiento para preparar fenil-carbamatos sustituidos |
| US5246912A (en) * | 1984-02-29 | 1993-09-21 | Berol Nobel (Suisse) S.A. | Herbicidal compositions of phenmedipham and desmedipham |
| CZ156191A3 (en) * | 1984-02-29 | 1995-10-18 | Schering Ag | Stabilized liquid herbicidal agent and method of controlling weed |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1344934A (fr) * | 1962-08-23 | 1963-12-06 | Progil | Préparation d'esters carbamiques |
| US3296201A (en) * | 1962-11-08 | 1967-01-03 | Du Pont | Nu-phenyl aromatic polymers |
| FR1498834A (fr) * | 1964-12-18 | 1967-10-20 | Fmc Corp | Herbicides à base de m-(carbamoyloxy)-carbanilates |
-
1981
- 1981-08-10 FR FR8115577A patent/FR2510994A1/fr active Granted
-
1982
- 1982-07-27 IT IT8222593A patent/IT1157312B/it active
- 1982-08-04 IL IL66464A patent/IL66464A0/xx unknown
- 1982-08-05 LU LU84320A patent/LU84320A1/fr unknown
- 1982-08-06 NL NL8203123A patent/NL8203123A/nl not_active Application Discontinuation
- 1982-08-06 JP JP57137150A patent/JPS58185551A/ja active Pending
- 1982-08-09 ES ES514848A patent/ES514848A0/es active Granted
- 1982-08-09 DD DD82242354A patent/DD202232A5/de unknown
- 1982-08-09 DK DK356582A patent/DK356582A/da not_active Application Discontinuation
- 1982-08-09 DE DE19823229589 patent/DE3229589A1/de not_active Withdrawn
- 1982-08-09 GB GB08222879A patent/GB2104519A/en not_active Withdrawn
- 1982-08-09 BE BE0/208774A patent/BE894062A/fr not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1344934A (fr) * | 1962-08-23 | 1963-12-06 | Progil | Préparation d'esters carbamiques |
| US3296201A (en) * | 1962-11-08 | 1967-01-03 | Du Pont | Nu-phenyl aromatic polymers |
| FR1498834A (fr) * | 1964-12-18 | 1967-10-20 | Fmc Corp | Herbicides à base de m-(carbamoyloxy)-carbanilates |
Also Published As
| Publication number | Publication date |
|---|---|
| IL66464A0 (en) | 1982-12-31 |
| BE894062A (fr) | 1983-02-09 |
| LU84320A1 (fr) | 1984-03-23 |
| ES8306102A1 (es) | 1983-05-01 |
| GB2104519A (en) | 1983-03-09 |
| IT8222593A0 (it) | 1982-07-27 |
| DE3229589A1 (de) | 1983-02-24 |
| DD202232A5 (de) | 1983-09-07 |
| FR2510994B1 (enExample) | 1984-07-13 |
| DK356582A (da) | 1983-02-11 |
| IT1157312B (it) | 1987-02-11 |
| NL8203123A (nl) | 1983-03-01 |
| JPS58185551A (ja) | 1983-10-29 |
| ES514848A0 (es) | 1983-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |