CS235046B2 - Method of n-phosphonomethylglycine preparation - Google Patents
Method of n-phosphonomethylglycine preparation Download PDFInfo
- Publication number
- CS235046B2 CS235046B2 CS835158A CS515883A CS235046B2 CS 235046 B2 CS235046 B2 CS 235046B2 CS 835158 A CS835158 A CS 835158A CS 515883 A CS515883 A CS 515883A CS 235046 B2 CS235046 B2 CS 235046B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- phosphonomethylglycine
- compound
- diketopiperazine
- molecular weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 phosphorus compound Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000011574 phosphorus Substances 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
- 239000011707 mineral Substances 0.000 claims abstract description 7
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000003839 salts Chemical group 0.000 claims description 11
- 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 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 11
- 230000002363 herbicidal effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 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 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000203 mixture 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical class CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- DGPSXMJBNDMVBE-UHFFFAOYSA-N OC(=O)CNC(F)(F)F Chemical class OC(=O)CNC(F)(F)F DGPSXMJBNDMVBE-UHFFFAOYSA-N 0.000 description 1
- UNVGGERHRPPCFM-UHFFFAOYSA-N OP(=C)=O.NCC(O)=O Chemical compound OP(=C)=O.NCC(O)=O UNVGGERHRPPCFM-UHFFFAOYSA-N 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 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
- 238000009835 boiling Methods 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
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000009306 commercial farming Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 235000005822 corn Nutrition 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
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035876 healing Effects 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
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 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
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 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 |
|---|---|
| CS235046B2 true CS235046B2 (en) | 1985-04-16 |
Family
ID=23595035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS835158A CS235046B2 (en) | 1982-07-29 | 1983-07-07 | Method of n-phosphonomethylglycine preparation |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4400330A (pl) |
| EP (1) | EP0102694B1 (pl) |
| JP (1) | JPS5929698A (pl) |
| KR (1) | KR840005460A (pl) |
| AR (1) | AR231451A1 (pl) |
| AT (1) | ATE29500T1 (pl) |
| AU (1) | AU552195B2 (pl) |
| BR (1) | BR8303922A (pl) |
| CA (1) | CA1205486A (pl) |
| CS (1) | CS235046B2 (pl) |
| DD (1) | DD213220A5 (pl) |
| DE (1) | DE3373479D1 (pl) |
| DK (1) | DK299483A (pl) |
| ES (1) | ES523938A0 (pl) |
| IL (1) | IL69096A0 (pl) |
| PL (1) | PL140398B1 (pl) |
| RO (1) | RO87040B (pl) |
| ZA (1) | ZA834683B (pl) |
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 |
| US4694081A (en) * | 1985-09-23 | 1987-09-15 | Monsanto Company | Process to prepare 2,5-diketopiperazines |
| US4694082A (en) * | 1985-09-23 | 1987-09-15 | Monsanto Company | Compound 1,4-diisopropyl-2,5-diketopiperazine |
| US4804499A (en) * | 1985-09-23 | 1989-02-14 | Monsanto Company | Process for the preparation of N-substituted aminomethylphosphonic acids |
| US5352461A (en) * | 1992-03-11 | 1994-10-04 | Pharmaceutical Discovery Corporation | Self assembling diketopiperazine drug delivery system |
| JP2001511810A (ja) | 1997-02-13 | 2001-08-14 | モンサント カンパニー | アミノカルボン酸の製造方法 |
| ID28485A (id) | 1998-08-12 | 2001-05-31 | Monsanto Co | Proses yang terus berlangsung untuk pembuatan asam n-(fosfonometil) iminodiasetat |
| WO2014012990A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
| BR112015000988A2 (pt) * | 2012-07-17 | 2017-06-27 | Straitmark Holding Ag | método para a síntese de ácido n-fosfonometiliminodiacético ou derivados do mesmo |
| BR112015000995B1 (pt) | 2012-07-17 | 2020-04-28 | Monsanto Technology Llc | método para a síntese de n-(fosfonometil)glicina ou um de seus derivados selecionados a partir do grupo que consiste em seus sais, seus ésteres de fosfonato e seus sais de éster de fosfonato |
| IN2015DN01079A (pl) | 2012-07-17 | 2015-06-26 | Straitmark Holding Ag |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2959590A (en) * | 1960-11-08 | Chz-chz | ||
| NL285361A (pl) * | 1961-11-13 | 1900-01-01 | ||
| 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 AT AT83303561T patent/ATE29500T1/de not_active IP Right Cessation
- 1983-06-21 EP EP83303561A patent/EP0102694B1/en not_active Expired
- 1983-06-21 CA CA000430889A patent/CA1205486A/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 JP JP58115299A patent/JPS5929698A/ja active Pending
- 1983-06-28 IL IL69096A patent/IL69096A0/xx unknown
- 1983-06-29 DK DK299483A patent/DK299483A/da not_active Application Discontinuation
- 1983-07-07 ES ES523938A patent/ES523938A0/es active Granted
- 1983-07-07 CS CS835158A patent/CS235046B2/cs unknown
- 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 DD DD83253492A patent/DD213220A5/de unknown
- 1983-07-28 KR KR1019830003518A patent/KR840005460A/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE29500T1 (de) | 1987-09-15 |
| ES8500959A1 (es) | 1984-11-01 |
| EP0102694B1 (en) | 1987-09-09 |
| DE3373479D1 (en) | 1987-10-15 |
| AR231451A1 (es) | 1984-11-30 |
| RO87040A (ro) | 1985-06-29 |
| ES523938A0 (es) | 1984-11-01 |
| DD213220A5 (de) | 1984-09-05 |
| CA1205486A (en) | 1986-06-03 |
| KR840005460A (ko) | 1984-11-12 |
| ZA834683B (en) | 1985-02-27 |
| BR8303922A (pt) | 1984-04-24 |
| EP0102694A1 (en) | 1984-03-14 |
| DK299483D0 (da) | 1983-06-29 |
| PL243175A1 (en) | 1984-07-30 |
| IL69096A0 (en) | 1983-10-31 |
| DK299483A (da) | 1984-01-30 |
| RO87040B (ro) | 1985-06-30 |
| US4400330A (en) | 1983-08-23 |
| PL140398B1 (en) | 1987-04-30 |
| AU1627783A (en) | 1984-02-02 |
| JPS5929698A (ja) | 1984-02-16 |
| AU552195B2 (en) | 1986-05-22 |
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