DE2007160A1 - Biologische wirksame Benzthiadiazole - Google Patents
Biologische wirksame BenzthiadiazoleInfo
- Publication number
- DE2007160A1 DE2007160A1 DE19702007160 DE2007160A DE2007160A1 DE 2007160 A1 DE2007160 A1 DE 2007160A1 DE 19702007160 DE19702007160 DE 19702007160 DE 2007160 A DE2007160 A DE 2007160A DE 2007160 A1 DE2007160 A1 DE 2007160A1
- Authority
- DE
- Germany
- Prior art keywords
- benzthiadiazole
- formula
- chloro
- melting point
- compound
- 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
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 4
- -1 Hydroxycarbonylmethoxy Chemical group 0.000 description 76
- 230000008018 melting Effects 0.000 description 60
- 238000002844 melting Methods 0.000 description 60
- 239000004480 active ingredient Substances 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 28
- 239000000126 substance Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000004048 modification Effects 0.000 description 18
- 238000012986 modification Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
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- 239000000203 mixture Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 240000003173 Drymaria cordata Species 0.000 description 8
- 240000003705 Senecio vulgaris Species 0.000 description 8
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- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
- 240000003768 Solanum lycopersicum Species 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000012876 carrier material Substances 0.000 description 6
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- 235000003805 Musa ABB Group Nutrition 0.000 description 5
- 235000015266 Plantago major Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 244000274883 Urtica dioica Species 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
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- 238000002474 experimental method Methods 0.000 description 5
- 230000009036 growth inhibition Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- SIZDQTFXNGXUNV-UHFFFAOYSA-N ethyl 2-(2,1,3-benzothiadiazol-4-yloxy)acetate Chemical compound CCOC(=O)COC1=CC=CC2=NSN=C12 SIZDQTFXNGXUNV-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
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- 230000008719 thickening Effects 0.000 description 4
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
- PIRWHKMXKJQNOW-UHFFFAOYSA-N 4-methoxy-2,1,3-benzothiadiazole Chemical class COC1=CC=CC2=NSN=C12 PIRWHKMXKJQNOW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000032544 Cicatrix Diseases 0.000 description 3
- 241001473402 Hieracium Species 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
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- 239000000314 lubricant Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
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- 231100000241 scar Toxicity 0.000 description 3
- 230000037387 scars Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- YRSSHOVRSMQULE-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzonitrile Chemical compound OC1=C(Cl)C=C(C#N)C=C1Cl YRSSHOVRSMQULE-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000011293 Brassica napus Nutrition 0.000 description 2
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 2
- 208000027534 Emotional disease Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 244000211187 Lepidium sativum Species 0.000 description 2
- 235000007849 Lepidium sativum Nutrition 0.000 description 2
- 241000234295 Musa Species 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 241001552576 Picris hieracioides Species 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
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- 235000012211 aluminium silicate Nutrition 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
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- 229930002875 chlorophyll Natural products 0.000 description 2
- 235000019804 chlorophyll Nutrition 0.000 description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 2
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
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- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 2
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- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 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 2
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
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- GKVJYBKEHWXTEF-UHFFFAOYSA-N 4-chloro-5-methoxy-2-nitroaniline Chemical compound COC1=CC(N)=C([N+]([O-])=O)C=C1Cl GKVJYBKEHWXTEF-UHFFFAOYSA-N 0.000 description 1
- UEGRPBWFVBWAGM-UHFFFAOYSA-N 5,6-dichloro-1,2,3-benzothiadiazole Chemical compound C1=C(Cl)C(Cl)=CC2=C1SN=N2 UEGRPBWFVBWAGM-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
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- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Cultivation Of Plants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6902637A NL6902637A (enrdf_load_stackoverflow) | 1969-02-19 | 1969-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2007160A1 true DE2007160A1 (de) | 1971-01-07 |
Family
ID=19806200
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702007160 Pending DE2007160A1 (de) | 1969-02-19 | 1970-02-17 | Biologische wirksame Benzthiadiazole |
| DE19702041196 Pending DE2041196A1 (de) | 1969-02-19 | 1970-02-17 | Praeparate zur Beeinflussung des Wachstums von Pflanzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702041196 Pending DE2041196A1 (de) | 1969-02-19 | 1970-02-17 | Praeparate zur Beeinflussung des Wachstums von Pflanzen |
Country Status (17)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2214632A1 (de) * | 1972-03-23 | 1973-10-04 | Schering Ag | 1,2,3-thiadiazolderivate |
| DE2324732A1 (de) * | 1973-05-14 | 1974-12-12 | Schering Ag | Phenyl-thiadiazolyl-thioharnstoff |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5559037A (en) * | 1978-10-25 | 1980-05-02 | Tatsuo Arakawa | Support metal for car antenna |
| JPH01149095U (enrdf_load_stackoverflow) * | 1988-04-06 | 1989-10-16 | ||
| MXPA05003607A (es) | 2002-10-04 | 2005-11-17 | Prana Biotechnology Ltd | Compuestos neurologicamente activos. |
| CN113735864B (zh) * | 2021-07-30 | 2022-04-15 | 江苏师范大学 | 一种d-苯并噻二唑-tb(-d)衍生物及其合成方法与应用 |
-
1969
- 1969-02-19 NL NL6902637A patent/NL6902637A/xx unknown
-
1970
- 1970-02-09 ZA ZA700872A patent/ZA70872B/xx unknown
- 1970-02-16 IE IE195/70A patent/IE34208B1/xx unknown
- 1970-02-16 CH CH218870A patent/CH562817A5/xx not_active IP Right Cessation
- 1970-02-16 CH CH1625972A patent/CH551136A/xx not_active IP Right Cessation
- 1970-02-16 SE SE7001942A patent/SE377693B/xx unknown
- 1970-02-16 GB GB731470A patent/GB1303711A/en not_active Expired
- 1970-02-16 IL IL33903A patent/IL33903A/en unknown
- 1970-02-16 DK DK74670*#A patent/DK133123C/da active
- 1970-02-17 BE BE746103D patent/BE746103A/xx unknown
- 1970-02-17 CS CS1087A patent/CS170144B2/cs unknown
- 1970-02-17 DE DE19702007160 patent/DE2007160A1/de active Pending
- 1970-02-17 AT AT141070A patent/AT301250B/de not_active IP Right Cessation
- 1970-02-17 DE DE19702041196 patent/DE2041196A1/de active Pending
- 1970-02-17 ES ES376641A patent/ES376641A1/es not_active Expired
- 1970-02-18 FR FR7005761A patent/FR2035597A5/fr not_active Expired
- 1970-02-19 CA CA075275A patent/CA934761A/en not_active Expired
- 1970-02-19 JP JP1387570A patent/JPS531334B1/ja active Pending
- 1970-02-19 BR BR216863/70A patent/BR7016863D0/pt unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2214632A1 (de) * | 1972-03-23 | 1973-10-04 | Schering Ag | 1,2,3-thiadiazolderivate |
| DE2324732A1 (de) * | 1973-05-14 | 1974-12-12 | Schering Ag | Phenyl-thiadiazolyl-thioharnstoff |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA70872B (en) | 1971-09-29 |
| JPS531334B1 (enrdf_load_stackoverflow) | 1978-01-18 |
| IL33903A0 (en) | 1970-04-20 |
| DK133123C (da) | 1976-09-06 |
| FR2035597A5 (enrdf_load_stackoverflow) | 1970-12-18 |
| IE34208L (en) | 1970-08-19 |
| IE34208B1 (en) | 1975-03-05 |
| SE377693B (enrdf_load_stackoverflow) | 1975-07-21 |
| BR7016863D0 (pt) | 1973-05-31 |
| GB1303711A (enrdf_load_stackoverflow) | 1973-01-17 |
| CA934761A (en) | 1973-10-02 |
| ES376641A1 (es) | 1972-09-16 |
| NL6902637A (enrdf_load_stackoverflow) | 1970-08-21 |
| DE2041196A1 (de) | 1971-04-29 |
| CH562817A5 (enrdf_load_stackoverflow) | 1975-06-13 |
| DK133123B (da) | 1976-03-29 |
| CS170144B2 (enrdf_load_stackoverflow) | 1976-08-27 |
| CH551136A (de) | 1974-07-15 |
| AT301250B (de) | 1972-08-25 |
| IL33903A (en) | 1976-07-30 |
| BE746103A (fr) | 1970-08-17 |
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