JPS5910351B2 - ３−オキシ−１，２，４−トリアゾ−ル誘導体の製造方法 - Google Patents
３−オキシ−１，２，４−トリアゾ−ル誘導体の製造方法Info
- Publication number
- JPS5910351B2 JPS5910351B2 JP50104879A JP10487975A JPS5910351B2 JP S5910351 B2 JPS5910351 B2 JP S5910351B2 JP 50104879 A JP50104879 A JP 50104879A JP 10487975 A JP10487975 A JP 10487975A JP S5910351 B2 JPS5910351 B2 JP S5910351B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- carbon atoms
- oxy
- solution
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- -1 2-substituted, 2-cyanohydrazinecarboxylic acid ester Chemical class 0.000 claims description 10
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PVZDOUYIWSZEAW-UHFFFAOYSA-N ethyl n-[cyano(propan-2-yl)amino]carbamate Chemical compound CCOC(=O)NN(C#N)C(C)C PVZDOUYIWSZEAW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- CWUWXTPGCLRBFM-UHFFFAOYSA-N ethyl n-[cyano(ethyl)amino]carbamate Chemical compound CCOC(=O)NN(CC)C#N CWUWXTPGCLRBFM-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XXIJEABMFHPQON-UHFFFAOYSA-N ethyl n-(methylamino)carbamate Chemical compound CCOC(=O)NNC XXIJEABMFHPQON-UHFFFAOYSA-N 0.000 description 2
- GLEPDFWPHDUTMJ-UHFFFAOYSA-N ethyl n-(propan-2-ylamino)carbamate Chemical compound CCOC(=O)NNC(C)C GLEPDFWPHDUTMJ-UHFFFAOYSA-N 0.000 description 2
- NTXLVYSQEUYSFS-UHFFFAOYSA-N ethyl n-[cyano(cyclopentyl)amino]carbamate Chemical compound CCOC(=O)NN(C#N)C1CCCC1 NTXLVYSQEUYSFS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- CWYKSVVUHGYPDF-UHFFFAOYSA-N ethyl n-(ethylamino)carbamate Chemical compound CCNNC(=O)OCC CWYKSVVUHGYPDF-UHFFFAOYSA-N 0.000 description 1
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003349 semicarbazides Chemical group 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1177174A CH601266A5 (OSRAM) | 1974-08-29 | 1974-08-29 | |
| CH1177174 | 1974-08-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5148668A JPS5148668A (en) | 1976-04-26 |
| JPS5910351B2 true JPS5910351B2 (ja) | 1984-03-08 |
Family
ID=4376715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50104879A Expired JPS5910351B2 (ja) | 1974-08-29 | 1975-08-29 | ３−オキシ−１，２，４−トリアゾ−ル誘導体の製造方法 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5910351B2 (OSRAM) |
| AT (1) | AT342587B (OSRAM) |
| AU (1) | AU499371B2 (OSRAM) |
| BE (1) | BE832830A (OSRAM) |
| CA (1) | CA1070696A (OSRAM) |
| CH (1) | CH601266A5 (OSRAM) |
| CS (1) | CS193522B2 (OSRAM) |
| DD (1) | DD122535A5 (OSRAM) |
| DE (1) | DE2537973A1 (OSRAM) |
| ES (1) | ES440532A1 (OSRAM) |
| FR (1) | FR2283132A1 (OSRAM) |
| GB (1) | GB1512456A (OSRAM) |
| HU (1) | HU172771B (OSRAM) |
| IL (1) | IL48008A (OSRAM) |
| NL (1) | NL7510012A (OSRAM) |
| NZ (1) | NZ178271A (OSRAM) |
| SU (1) | SU577989A3 (OSRAM) |
| ZA (1) | ZA755512B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3070073D1 (en) * | 1979-10-22 | 1985-03-14 | Glaxo Group Ltd | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
| GB2064515B (en) * | 1979-10-23 | 1983-06-29 | Glaxo Group Ltd | Heterocyclic derivatives processes for their production and pharmaceutical compositions containing them |
| ES511107A0 (es) * | 1981-04-09 | 1983-02-01 | Hoechst Ag | "procedimiento para la preparacion de 3-hidroxi-1,2,4-triazoles". |
| DE3939952A1 (de) * | 1989-12-02 | 1991-06-06 | Bayer Ag | Substituierte triazolinone |
| MY113324A (en) * | 1994-11-21 | 2002-01-31 | Bayer Ip Gmbh | Triazolyl derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792451A (fr) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | Esters triazolyliques d'acides phosphores et produits pesticides qui encontiennent |
| BE792449A (fr) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | Esters triazolyliques d'acides oxygenes du phosphore et produits pesticides qui en renferment |
| IL42316A (en) * | 1972-06-16 | 1976-02-29 | Ciba Geigy Ag | Triazolyl organophosphorus derivatives,their manufacture and their use as pesticides |
| DE2250572A1 (de) * | 1972-10-14 | 1974-04-18 | Bayer Ag | N,n-dimethyl-o-triazolyl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| NL7316469A (OSRAM) * | 1972-12-08 | 1974-06-11 | ||
| DE2301400C2 (de) * | 1973-01-12 | 1984-12-13 | Bayer Ag, 5090 Leverkusen | 0-Triazolyl-thionophosphor(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide |
-
1974
- 1974-08-29 CH CH1177174A patent/CH601266A5/xx not_active IP Right Cessation
-
1975
- 1975-07-31 NZ NZ178271A patent/NZ178271A/xx unknown
- 1975-08-15 CS CS755621A patent/CS193522B2/cs unknown
- 1975-08-18 SU SU7502163216A patent/SU577989A3/ru active
- 1975-08-25 NL NL7510012A patent/NL7510012A/xx not_active Application Discontinuation
- 1975-08-26 DE DE19752537973 patent/DE2537973A1/de active Granted
- 1975-08-27 HU HU75CI00001600A patent/HU172771B/hu unknown
- 1975-08-27 CA CA234,232A patent/CA1070696A/en not_active Expired
- 1975-08-27 GB GB35411/75A patent/GB1512456A/en not_active Expired
- 1975-08-27 DD DD188052A patent/DD122535A5/xx unknown
- 1975-08-28 AU AU84345/75A patent/AU499371B2/en not_active Expired
- 1975-08-28 AT AT664775A patent/AT342587B/de active
- 1975-08-28 ZA ZA00755512A patent/ZA755512B/xx unknown
- 1975-08-28 BE BE159531A patent/BE832830A/xx not_active IP Right Cessation
- 1975-08-28 IL IL48008A patent/IL48008A/xx unknown
- 1975-08-28 FR FR7526487A patent/FR2283132A1/fr active Granted
- 1975-08-28 ES ES440532A patent/ES440532A1/es not_active Expired
- 1975-08-29 JP JP50104879A patent/JPS5910351B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2537973A1 (de) | 1976-03-11 |
| NZ178271A (en) | 1978-04-03 |
| GB1512456A (en) | 1978-06-01 |
| JPS5148668A (en) | 1976-04-26 |
| CS193522B2 (en) | 1979-10-31 |
| IL48008A0 (en) | 1975-11-25 |
| AU499371B2 (en) | 1979-04-12 |
| BE832830A (fr) | 1976-03-01 |
| AT342587B (de) | 1978-04-10 |
| DD122535A5 (OSRAM) | 1976-10-12 |
| ZA755512B (en) | 1976-07-28 |
| ES440532A1 (es) | 1977-03-01 |
| HU172771B (hu) | 1978-12-28 |
| SU577989A3 (ru) | 1977-10-25 |
| DE2537973C2 (OSRAM) | 1989-04-06 |
| ATA664775A (de) | 1977-08-15 |
| AU8434575A (en) | 1977-03-03 |
| CH601266A5 (OSRAM) | 1978-06-30 |
| NL7510012A (nl) | 1976-03-02 |
| FR2283132B1 (OSRAM) | 1978-04-07 |
| FR2283132A1 (fr) | 1976-03-26 |
| CA1070696A (en) | 1980-01-29 |
| IL48008A (en) | 1979-07-25 |
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