DE2515371C2 - Verfahren zur Herstellung von cis-9-Tetradecenal und cis-11-Hexadecenal sowie diese Stoffe enthaltendes Sex-Attraktans für die Männchen der Tabakmotte - Google Patents
Verfahren zur Herstellung von cis-9-Tetradecenal und cis-11-Hexadecenal sowie diese Stoffe enthaltendes Sex-Attraktans für die Männchen der TabakmotteInfo
- Publication number
- DE2515371C2 DE2515371C2 DE2515371A DE2515371A DE2515371C2 DE 2515371 C2 DE2515371 C2 DE 2515371C2 DE 2515371 A DE2515371 A DE 2515371A DE 2515371 A DE2515371 A DE 2515371A DE 2515371 C2 DE2515371 C2 DE 2515371C2
- Authority
- DE
- Germany
- Prior art keywords
- cis
- hexadecenal
- tetradecenal
- male
- substances
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 18
- ANJAOCICJSRZSR-WAYWQWQTSA-N 9Z-Tetradecenal Chemical compound CCCC\C=C/CCCCCCCC=O ANJAOCICJSRZSR-WAYWQWQTSA-N 0.000 title claims description 13
- ANJAOCICJSRZSR-UHFFFAOYSA-N Z9-14:Ald Natural products CCCCC=CCCCCCCCC=O ANJAOCICJSRZSR-UHFFFAOYSA-N 0.000 title claims description 13
- 239000000126 substance Substances 0.000 title claims description 11
- AMTITFMUKRZZEE-WAYWQWQTSA-N (Z)-hexadec-11-enal Chemical compound CCCC\C=C/CCCCCCCCCC=O AMTITFMUKRZZEE-WAYWQWQTSA-N 0.000 title claims description 9
- AMTITFMUKRZZEE-UHFFFAOYSA-N Z11-16:Ald Natural products CCCCC=CCCCCCCCCCC=O AMTITFMUKRZZEE-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000877 Sex Attractant Substances 0.000 title claims description 4
- 230000008569 process Effects 0.000 title claims description 4
- 241001555556 Ephestia elutella Species 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 229940117975 chromium trioxide Drugs 0.000 claims description 7
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 7
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000005667 attractant Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000031902 chemoattractant activity Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 241000256244 Heliothis virescens Species 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000255967 Helicoverpa zea Species 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- GSAAJQNJNPBBSX-UHFFFAOYSA-N (E)-form-9-Tetradecen-1-ol Natural products CCCCC=CCCCCCCCCO GSAAJQNJNPBBSX-UHFFFAOYSA-N 0.000 description 2
- YDFAJMDFCCJZSI-UHFFFAOYSA-N 8-chlorooctan-1-ol Chemical compound OCCCCCCCCCl YDFAJMDFCCJZSI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 101100108536 Rattus norvegicus Aldh3a1 gene Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- 238000010793 Steam injection (oil industry) Methods 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- RHVMNRHQWXIJIS-UHFFFAOYSA-N Z11-16:OH Natural products CCCCC=CCCCCCCCCCCO RHVMNRHQWXIJIS-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- -1 ethanol ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000003016 pheromone Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- XXPBOEBNDHAAQH-UHFFFAOYSA-N (Z)-12-Tetradecenyl acetate Natural products CCCCC=CCCCCCCCCOC(C)=O XXPBOEBNDHAAQH-UHFFFAOYSA-N 0.000 description 1
- XVWSFDAKJCLUGG-QXMHVHEDSA-N (z)-hexadec-5-enal Chemical compound CCCCCCCCCC\C=C/CCCC=O XVWSFDAKJCLUGG-QXMHVHEDSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- OTUSESJECXGMIV-UHFFFAOYSA-N 10-chlorodecan-1-ol Chemical compound OCCCCCCCCCCCl OTUSESJECXGMIV-UHFFFAOYSA-N 0.000 description 1
- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- XXPBOEBNDHAAQH-SREVYHEPSA-N 9Z-Tetradecenyl acetate Chemical compound CCCC\C=C/CCCCCCCCOC(C)=O XXPBOEBNDHAAQH-SREVYHEPSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- LQKRYVGRPXFFAV-UHFFFAOYSA-N Phenylmethylglycidic ester Chemical compound CCOC(=O)C1OC1(C)C1=CC=CC=C1 LQKRYVGRPXFFAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 244000144987 brood Species 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catching Or Destruction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US460633A US3917711A (en) | 1974-04-12 | 1974-04-12 | Novel attractant components for males of the tobacco budworm moth |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2515371A1 DE2515371A1 (de) | 1975-10-23 |
| DE2515371C2 true DE2515371C2 (de) | 1984-05-17 |
Family
ID=23829476
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2515371A Expired DE2515371C2 (de) | 1974-04-12 | 1975-04-09 | Verfahren zur Herstellung von cis-9-Tetradecenal und cis-11-Hexadecenal sowie diese Stoffe enthaltendes Sex-Attraktans für die Männchen der Tabakmotte |
| DE2560502A Expired DE2560502C2 (de) | 1974-04-12 | 1975-04-09 | Verfahren zum Fangen und zum Desorientieren der Männchen der Tabakmotte |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2560502A Expired DE2560502C2 (de) | 1974-04-12 | 1975-04-09 | Verfahren zum Fangen und zum Desorientieren der Männchen der Tabakmotte |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3917711A (enExample) |
| JP (1) | JPS5756886B2 (enExample) |
| CA (1) | CA1049561A (enExample) |
| CH (1) | CH633412A5 (enExample) |
| DE (2) | DE2515371C2 (enExample) |
| ES (1) | ES436420A1 (enExample) |
| FR (1) | FR2267298B3 (enExample) |
| GB (1) | GB1474880A (enExample) |
| IT (1) | IT1041750B (enExample) |
| NL (1) | NL7503170A (enExample) |
| ZA (1) | ZA752314B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6010004B2 (ja) * | 1980-09-01 | 1985-03-14 | 日東電工株式会社 | フエロモン徐放デイスペンサ− |
| US4560792A (en) * | 1982-07-20 | 1985-12-24 | Phillips Petroleum Company | Disproportionation of functional olefins |
| US4540826A (en) * | 1983-08-12 | 1985-09-10 | Phillips Petroleum Company | Process for preparing olefinic aldehydes |
| US4740627A (en) * | 1987-05-21 | 1988-04-26 | Phillips Petroleum Company | Synthesis of E,Z-11-tetradecen-1-al |
| US4843178A (en) * | 1987-12-02 | 1989-06-27 | Byers Jim D | Compositions possessing pheromone-like activity |
| US6080418A (en) * | 1997-04-07 | 2000-06-27 | 3M Innovative Properties Company | Suspensions of microcapsules containing biologically active ingredients and adhesive microspheres |
| US6248364B1 (en) | 1997-04-07 | 2001-06-19 | 3M Innovative Properties Company | Encapsulation process and encapsulated products |
| JP2005247814A (ja) * | 2004-03-08 | 2005-09-15 | Seiko Epson Corp | 散布方法及び害虫防除方法 |
| CN105248391A (zh) * | 2015-11-11 | 2016-01-20 | 云南省烟草农业科学研究院 | 性引诱剂防治烟草害虫烟青虫的方法 |
| CN114672422A (zh) * | 2022-03-08 | 2022-06-28 | 南京工业大学 | 一种产顺-11-十六碳烯醛破囊壶菌菌株的培育方法 |
-
1974
- 1974-04-12 US US460633A patent/US3917711A/en not_active Expired - Lifetime
-
1975
- 1975-03-11 GB GB996575A patent/GB1474880A/en not_active Expired
- 1975-03-18 NL NL7503170A patent/NL7503170A/xx unknown
- 1975-04-03 CA CA223,771A patent/CA1049561A/en not_active Expired
- 1975-04-08 ES ES436420A patent/ES436420A1/es not_active Expired
- 1975-04-09 DE DE2515371A patent/DE2515371C2/de not_active Expired
- 1975-04-09 DE DE2560502A patent/DE2560502C2/de not_active Expired
- 1975-04-11 FR FR7511430A patent/FR2267298B3/fr not_active Expired
- 1975-04-11 ZA ZA00752314A patent/ZA752314B/xx unknown
- 1975-04-12 JP JP50044749A patent/JPS5756886B2/ja not_active Expired
- 1975-04-12 CH CH475075A patent/CH633412A5/it not_active IP Right Cessation
- 1975-04-14 IT IT7522301Q patent/IT1041750B/it active
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1049561A (en) | 1979-02-27 |
| AU7929175A (en) | 1976-09-23 |
| CH633412A5 (it) | 1982-12-15 |
| JPS50140628A (enExample) | 1975-11-11 |
| DE2515371A1 (de) | 1975-10-23 |
| US3917711A (en) | 1975-11-04 |
| ES436420A1 (es) | 1977-04-01 |
| IT1041750B (it) | 1980-01-10 |
| JPS5756886B2 (enExample) | 1982-12-02 |
| FR2267298A1 (enExample) | 1975-11-07 |
| GB1474880A (en) | 1977-05-25 |
| NL7503170A (nl) | 1975-10-14 |
| DE2560502C2 (de) | 1985-02-14 |
| FR2267298B3 (enExample) | 1978-10-06 |
| ZA752314B (en) | 1976-04-28 |
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