JPS58185551A - 除草剤フエンメジフアムの製造方法 - Google Patents
除草剤フエンメジフアムの製造方法Info
- Publication number
- JPS58185551A JPS58185551A JP57137150A JP13715082A JPS58185551A JP S58185551 A JPS58185551 A JP S58185551A JP 57137150 A JP57137150 A JP 57137150A JP 13715082 A JP13715082 A JP 13715082A JP S58185551 A JPS58185551 A JP S58185551A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- phosgene
- medium
- methanol
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000002363 herbicidal effect Effects 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 18
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 16
- -1 acetate ester Chemical class 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
- 229940018563 3-aminophenol Drugs 0.000 claims 1
- ONZMCAOKNAAURQ-UHFFFAOYSA-N OC=1C=C(C=CC1)NC(=O)Cl Chemical compound OC=1C=C(C=CC1)NC(=O)Cl ONZMCAOKNAAURQ-UHFFFAOYSA-N 0.000 claims 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 1
- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- IFEJLMHZNQJGQU-KXXGZHCCSA-M sodium;(z)-7-[(1r,2r,3r,5s)-2-[(e,3r)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate Chemical compound [Na+].C([C@H](O)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC([O-])=O)OC1=CC=CC(Cl)=C1 IFEJLMHZNQJGQU-KXXGZHCCSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 239000005594 Phenmedipham Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 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 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DFNWJUOJZVWDRT-UHFFFAOYSA-N 3-hydroxybenzoyl chloride Chemical compound OC1=CC=CC(C(Cl)=O)=C1 DFNWJUOJZVWDRT-UHFFFAOYSA-N 0.000 description 1
- 101100342994 Arabidopsis thaliana IIL1 gene Proteins 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 241001655798 Taku Species 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000007423 decrease Effects 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
- 235000013305 food Nutrition 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8115577 | 1981-08-10 | ||
| FR8115577A FR2510994A1 (fr) | 1981-08-10 | 1981-08-10 | Procede de preparation de l'herbicide phenmedipham |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58185551A true JPS58185551A (ja) | 1983-10-29 |
Family
ID=9261401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57137150A Pending JPS58185551A (ja) | 1981-08-10 | 1982-08-06 | 除草剤フエンメジフアムの製造方法 |
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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1054673A (enExample) * | 1962-08-23 | |||
| US3296201A (en) * | 1962-11-08 | 1967-01-03 | Du Pont | Nu-phenyl aromatic polymers |
| US3404975A (en) * | 1964-12-18 | 1968-10-08 | Fmc Corp | m-(carbamoyloxy)-carbanilates as herbicides |
-
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
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 |
| FR2510994A1 (fr) | 1983-02-11 |
| NL8203123A (nl) | 1983-03-01 |
| ES514848A0 (es) | 1983-05-01 |
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