DD213220A5 - Verfahren zur herstellung von n-phosphonomethylglycin - Google Patents
Verfahren zur herstellung von n-phosphonomethylglycin Download PDFInfo
- Publication number
- DD213220A5 DD213220A5 DD83253492A DD25349283A DD213220A5 DD 213220 A5 DD213220 A5 DD 213220A5 DD 83253492 A DD83253492 A DD 83253492A DD 25349283 A DD25349283 A DD 25349283A DD 213220 A5 DD213220 A5 DD 213220A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- item
- acid
- phosphonomethylglycine
- diketopiperazine
- bis
- Prior art date
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 11
- -1 phosphorus compound Chemical class 0.000 claims abstract description 11
- 239000011574 phosphorus Substances 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- 239000000376 reactant Substances 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- XNXADQRVRLZXAD-UHFFFAOYSA-N 2-(2-phosphonoethylamino)acetic acid Chemical class OC(=O)CNCCP(O)(O)=O XNXADQRVRLZXAD-UHFFFAOYSA-N 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 238000002791 soaking Methods 0.000 claims 1
- ROKAXOISGALEAP-UHFFFAOYSA-N [2,5-dioxo-4-(phosphonomethyl)piperazin-1-yl]methylphosphonic acid Chemical compound OP(O)(=O)CN1CC(=O)N(CP(O)(O)=O)CC1=O ROKAXOISGALEAP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- 239000004009 herbicide Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- DFRHETNXRZJTGA-UHFFFAOYSA-N 2-(phosphanylmethylamino)acetic acid Chemical compound OC(=O)CNCP DFRHETNXRZJTGA-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/403,239 US4400330A (en) | 1982-07-29 | 1982-07-29 | Method for preparation of N-phosphonomethylglycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD213220A5 true DD213220A5 (de) | 1984-09-05 |
Family
ID=23595035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83253492A DD213220A5 (de) | 1982-07-29 | 1983-07-28 | Verfahren zur herstellung von n-phosphonomethylglycin |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4400330A (ro) |
| EP (1) | EP0102694B1 (ro) |
| JP (1) | JPS5929698A (ro) |
| KR (1) | KR840005460A (ro) |
| AR (1) | AR231451A1 (ro) |
| AT (1) | ATE29500T1 (ro) |
| AU (1) | AU552195B2 (ro) |
| BR (1) | BR8303922A (ro) |
| CA (1) | CA1205486A (ro) |
| CS (1) | CS235046B2 (ro) |
| DD (1) | DD213220A5 (ro) |
| DE (1) | DE3373479D1 (ro) |
| DK (1) | DK299483A (ro) |
| ES (1) | ES523938A0 (ro) |
| IL (1) | IL69096A0 (ro) |
| PL (1) | PL140398B1 (ro) |
| RO (1) | RO87040B (ro) |
| ZA (1) | ZA834683B (ro) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4578224A (en) * | 1982-10-18 | 1986-03-25 | Stauffer Chemical Company | Method for preparation of salts of N-phosphonomethylglycine |
| DK467083A (da) * | 1982-10-18 | 1984-04-19 | Stauffer Chemical Co | Fremgangsmaade til fremstilling af n-phosphonomethylglycin |
| CA1248531A (en) * | 1984-04-17 | 1989-01-10 | Jeffrey C. Watkins | 4-substituted piperazine-2-carboxylic acids |
| US4804499A (en) * | 1985-09-23 | 1989-02-14 | Monsanto Company | Process for the preparation of N-substituted aminomethylphosphonic acids |
| US4694082A (en) * | 1985-09-23 | 1987-09-15 | Monsanto Company | Compound 1,4-diisopropyl-2,5-diketopiperazine |
| US4694081A (en) * | 1985-09-23 | 1987-09-15 | Monsanto Company | Process to prepare 2,5-diketopiperazines |
| US5352461A (en) * | 1992-03-11 | 1994-10-04 | Pharmaceutical Discovery Corporation | Self assembling diketopiperazine drug delivery system |
| CN1239473A (zh) * | 1997-02-13 | 1999-12-22 | 孟山都公司 | 制备氨基羧酸的方法 |
| ID28485A (id) | 1998-08-12 | 2001-05-31 | Monsanto Co | Proses yang terus berlangsung untuk pembuatan asam n-(fosfonometil) iminodiasetat |
| CN104812765B (zh) | 2012-07-17 | 2017-06-06 | 斯特雷特马克控股股份公司 | 用于合成α‑氨基亚烷基膦酸的方法 |
| ES2609488T3 (es) * | 2012-07-17 | 2017-04-20 | Straitmark Holding Ag | Método para la síntesis de N-(fosfonometil)glicina |
| CN104812766B (zh) | 2012-07-17 | 2017-06-06 | 斯特雷特马克控股股份公司 | 用于合成氨基亚烷基膦酸的方法 |
| BR112015000988A2 (pt) * | 2012-07-17 | 2017-06-27 | Straitmark Holding Ag | método para a síntese de ácido n-fosfonometiliminodiacético ou derivados do mesmo |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2959590A (en) * | 1960-11-08 | Chz-chz | ||
| CA775575A (en) * | 1961-11-13 | 1968-01-09 | R. Irani Riyad | Organic phosphorus compounds |
| US3954761A (en) * | 1968-10-17 | 1976-05-04 | Petrolite Corporation | Piperazine phosphonic acids |
| RO65811A (fr) * | 1974-06-26 | 1979-07-15 | Budapesti Vegyimuevek | Procede pour obtenir du n-phosphonombethyl-glycine |
| DE2434312A1 (de) * | 1974-07-17 | 1976-01-29 | Bayer Ag | Heterocyclische phosphonsaeureester |
| ES444490A1 (es) * | 1975-01-16 | 1977-09-16 | Chinoin Gyogyszer Es Vegyeszet | Procedimiento para la fabricacion de n-fosfono-metilglicina y sus intermedios. |
| US4053505A (en) * | 1976-01-05 | 1977-10-11 | Monsanto Company | Preparation of n-phosphonomethyl glycine |
-
1982
- 1982-07-29 US US06/403,239 patent/US4400330A/en not_active Expired - Fee Related
-
1983
- 1983-06-21 CA CA000430889A patent/CA1205486A/en not_active Expired
- 1983-06-21 AT AT83303561T patent/ATE29500T1/de not_active IP Right Cessation
- 1983-06-21 EP EP83303561A patent/EP0102694B1/en not_active Expired
- 1983-06-21 DE DE8383303561T patent/DE3373479D1/de not_active Expired
- 1983-06-27 AU AU16277/83A patent/AU552195B2/en not_active Ceased
- 1983-06-27 ZA ZA834683A patent/ZA834683B/xx unknown
- 1983-06-28 IL IL69096A patent/IL69096A0/xx unknown
- 1983-06-28 JP JP58115299A patent/JPS5929698A/ja active Pending
- 1983-06-29 DK DK299483A patent/DK299483A/da not_active Application Discontinuation
- 1983-07-07 CS CS835158A patent/CS235046B2/cs unknown
- 1983-07-07 ES ES523938A patent/ES523938A0/es active Granted
- 1983-07-08 AR AR293559A patent/AR231451A1/es active
- 1983-07-19 RO RO111668A patent/RO87040B/ro unknown
- 1983-07-22 BR BR8303922A patent/BR8303922A/pt unknown
- 1983-07-26 PL PL1983243175A patent/PL140398B1/pl unknown
- 1983-07-28 KR KR1019830003518A patent/KR840005460A/ko not_active IP Right Cessation
- 1983-07-28 DD DD83253492A patent/DD213220A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS235046B2 (en) | 1985-04-16 |
| DK299483A (da) | 1984-01-30 |
| IL69096A0 (en) | 1983-10-31 |
| BR8303922A (pt) | 1984-04-24 |
| KR840005460A (ko) | 1984-11-12 |
| DK299483D0 (da) | 1983-06-29 |
| ATE29500T1 (de) | 1987-09-15 |
| EP0102694A1 (en) | 1984-03-14 |
| PL243175A1 (en) | 1984-07-30 |
| US4400330A (en) | 1983-08-23 |
| AR231451A1 (es) | 1984-11-30 |
| AU1627783A (en) | 1984-02-02 |
| PL140398B1 (en) | 1987-04-30 |
| ES8500959A1 (es) | 1984-11-01 |
| RO87040B (ro) | 1985-06-30 |
| RO87040A (ro) | 1985-06-29 |
| ZA834683B (en) | 1985-02-27 |
| DE3373479D1 (en) | 1987-10-15 |
| JPS5929698A (ja) | 1984-02-16 |
| AU552195B2 (en) | 1986-05-22 |
| CA1205486A (en) | 1986-06-03 |
| EP0102694B1 (en) | 1987-09-09 |
| ES523938A0 (es) | 1984-11-01 |
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