CS198300B2 - Herbicide and method of producing the active ingredient - Google Patents
Herbicide and method of producing the active ingredient Download PDFInfo
- Publication number
- CS198300B2 CS198300B2 CS784254A CS425478A CS198300B2 CS 198300 B2 CS198300 B2 CS 198300B2 CS 784254 A CS784254 A CS 784254A CS 425478 A CS425478 A CS 425478A CS 198300 B2 CS198300 B2 CS 198300B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- compound
- halogen
- alkyl
- oxygen
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 39
- 239000004480 active ingredient Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 10
- 239000004009 herbicide Substances 0.000 title description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 150000002367 halogens Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 239000001301 oxygen Substances 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052717 sulfur Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
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- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
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- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 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 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- ZGNXATVKGIJQGC-UHFFFAOYSA-N piperidine-3-carbonitrile Chemical compound N#CC1CCCNC1 ZGNXATVKGIJQGC-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7740077A JPS5412344A (en) | 1977-06-28 | 1977-06-28 | Substituted phenylurea derivatives, their preparation and herbicides comprising |
| JP8874277A JPS5424855A (en) | 1977-07-22 | 1977-07-22 | Substituted phenylurea derivative, its preparation, and herbicide containing the same |
| JP2302678A JPS6052699B2 (ja) | 1978-02-28 | 1978-02-28 | 置換フェニル尿素誘導体、その製造法および該化合物からなる除草剤 |
| JP2792678A JPS54122251A (en) | 1978-03-10 | 1978-03-10 | Substituted phenylurea derivative, its preparation and herbicide containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS198300B2 true CS198300B2 (en) | 1980-05-30 |
Family
ID=27457880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784254A CS198300B2 (en) | 1977-06-28 | 1978-06-28 | Herbicide and method of producing the active ingredient |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4249938A (pl) |
| AU (1) | AU521992B2 (pl) |
| BE (1) | BE868406A (pl) |
| BR (1) | BR7804084A (pl) |
| CA (1) | CA1126757A (pl) |
| CH (1) | CH636853A5 (pl) |
| CS (1) | CS198300B2 (pl) |
| DD (1) | DD137438A5 (pl) |
| DE (1) | DE2828417A1 (pl) |
| DK (1) | DK291478A (pl) |
| ES (1) | ES471245A1 (pl) |
| FR (1) | FR2405928A1 (pl) |
| GB (1) | GB2000766B (pl) |
| HU (1) | HU180955B (pl) |
| NL (1) | NL7806912A (pl) |
| PL (1) | PL114407B1 (pl) |
| ZA (1) | ZA783669B (pl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4309212A (en) * | 1977-10-26 | 1982-01-05 | Sumitomo Chemical Company, Limited | Herbicidal compositions and methods employing urea derivatives |
| JPS54117445A (en) * | 1977-12-13 | 1979-09-12 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation, and herbicide containing the same |
| ZA793186B (en) * | 1978-07-06 | 1981-02-25 | Duphar Int Res | New urea and thiourea compounds, method of preparing the new compounds, as well as insecticidal compositions on the basis of these compounds |
| JPS5531039A (en) * | 1978-08-25 | 1980-03-05 | Sumitomo Chem Co Ltd | Oximecarbamate derivative, its preparation, and microbicide and herbicide containing the same |
| JPS55102553A (en) | 1979-01-30 | 1980-08-05 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation, herbicide and fungicide comprising it as active constituent |
| GB2046255B (en) | 1979-03-13 | 1983-05-11 | Sumitomo Chemical Co | Urea derivatives |
| US4376646A (en) * | 1980-03-18 | 1983-03-15 | Ciba-Geigy Corporation | Herbicidal N-[4-(3'-alkoxyphenoxy)-phenyl]-N'-methylureas |
| US4358309A (en) * | 1980-04-17 | 1982-11-09 | Chugai Seiyaku Kabushiki Kaisha | Urea derivatives and highly selective herbicidal compositions containing the same |
| JPS56167658A (en) | 1980-05-28 | 1981-12-23 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation and herbicide containing the same as active constituent |
| DE3148594A1 (de) * | 1981-12-09 | 1983-07-21 | Basf Ag, 6700 Ludwigshafen | Anilinderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| EP0119457B1 (de) * | 1983-02-23 | 1986-12-30 | Bayer Ag | Mittel zur Regulierung des Pflanzenwachstums |
| DE3324244A1 (de) * | 1983-07-06 | 1985-01-17 | Basf Ag, 6700 Ludwigshafen | Harnstoffderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| US5643591A (en) * | 1991-01-16 | 1997-07-01 | Fmc Corporation | Solid dosage forms |
| WO1998039289A1 (en) * | 1997-03-03 | 1998-09-11 | Nissan Chemical Industries, Ltd. | Urea derivatives, and industrial antibacterial and antifungal agents, algaecides and antiperiphytic agents containing the same |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE535847A (pl) * | 1954-02-18 | 1900-01-01 | ||
| US3252783A (en) * | 1961-04-11 | 1966-05-24 | Hooker Chemical Corp | Method of controlling plant growth |
| FR1489916A (fr) * | 1965-07-20 | 1967-07-28 | Bayer Ag | Procédé de préparation d'aminophényl-thioéthers |
| CH503459A (de) * | 1968-01-23 | 1971-02-28 | Ciba Geigy Ag | Schädlingsbekämpfungsmittel |
| CH532891A (de) * | 1969-03-26 | 1973-01-31 | Ciba Geigy Ag | Verwendung von Phenylharnstoffen zum selektiven Bekämpfen von Unkräutern in Kulturen von Nutzpflanzen |
| CH507646A (de) * | 1968-04-19 | 1971-05-31 | Ciba Geigy Ag | Selektives Herbizid |
| FR1597407A (pl) * | 1968-05-17 | 1970-06-29 | ||
| US3819697A (en) * | 1970-03-04 | 1974-06-25 | American Cyanamid Co | Substituted phenylurea herbicides |
| US3852339A (en) * | 1970-06-15 | 1974-12-03 | Squibb & Sons Inc | Aminoalkoxyphenylurea derivatives |
| DE2247310A1 (de) * | 1972-09-27 | 1974-04-04 | Bayer Ag | Tetrasubstituierte harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| JPS5344544A (en) * | 1976-09-30 | 1978-04-21 | Sumitomo Chem Co Ltd | Substituted phenylurea derivatives, their preparation, and selective herbicide comprising the corresponding compounds |
| JPS53108947A (en) * | 1977-03-03 | 1978-09-22 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its production and selective herbicide containing the same |
-
1978
- 1978-06-23 BE BE188805A patent/BE868406A/xx not_active IP Right Cessation
- 1978-06-27 CH CH699778A patent/CH636853A5/de not_active IP Right Cessation
- 1978-06-27 GB GB7828080A patent/GB2000766B/en not_active Expired
- 1978-06-27 FR FR7819211A patent/FR2405928A1/fr active Granted
- 1978-06-27 BR BR787804084A patent/BR7804084A/pt unknown
- 1978-06-27 NL NL7806912A patent/NL7806912A/xx not_active Application Discontinuation
- 1978-06-27 CA CA306,267A patent/CA1126757A/en not_active Expired
- 1978-06-27 US US05/919,683 patent/US4249938A/en not_active Expired - Lifetime
- 1978-06-27 ZA ZA00783669A patent/ZA783669B/xx unknown
- 1978-06-28 HU HU78SU979A patent/HU180955B/hu unknown
- 1978-06-28 AU AU37565/78A patent/AU521992B2/en not_active Expired
- 1978-06-28 DK DK291478A patent/DK291478A/da not_active Application Discontinuation
- 1978-06-28 CS CS784254A patent/CS198300B2/cs unknown
- 1978-06-28 DD DD78206344A patent/DD137438A5/xx unknown
- 1978-06-28 ES ES471245A patent/ES471245A1/es not_active Expired
- 1978-06-28 PL PL1978207986A patent/PL114407B1/pl unknown
- 1978-06-28 DE DE19782828417 patent/DE2828417A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2000766B (en) | 1982-01-20 |
| DD137438A5 (de) | 1979-09-05 |
| AU521992B2 (en) | 1982-05-13 |
| US4249938A (en) | 1981-02-10 |
| AU3756578A (en) | 1980-01-03 |
| PL114407B1 (en) | 1981-01-31 |
| PL207986A1 (pl) | 1979-11-19 |
| FR2405928B1 (pl) | 1982-09-17 |
| GB2000766A (en) | 1979-01-17 |
| NL7806912A (nl) | 1979-01-02 |
| CA1126757A (en) | 1982-06-29 |
| BE868406A (fr) | 1978-12-27 |
| ZA783669B (en) | 1979-06-27 |
| FR2405928A1 (fr) | 1979-05-11 |
| CH636853A5 (de) | 1983-06-30 |
| ES471245A1 (es) | 1979-10-01 |
| DK291478A (da) | 1978-12-29 |
| BR7804084A (pt) | 1979-01-16 |
| DE2828417A1 (de) | 1979-01-04 |
| HU180955B (en) | 1983-05-30 |
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