CA1074795A - Process for the preparation of novel phosphorylated thiophenic substances - Google Patents
Process for the preparation of novel phosphorylated thiophenic substancesInfo
- Publication number
- CA1074795A CA1074795A CA245,098A CA245098A CA1074795A CA 1074795 A CA1074795 A CA 1074795A CA 245098 A CA245098 A CA 245098A CA 1074795 A CA1074795 A CA 1074795A
- Authority
- CA
- Canada
- Prior art keywords
- dans
- radical
- atomes
- carbone
- soit
- 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
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 239000000126 substance Substances 0.000 title description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- FZTJMMWGVZSSKJ-UHFFFAOYSA-N (2-cyano-5-methylthiophen-3-yl) dimethyl phosphate Chemical compound COP(=O)(OC)OC=1C=C(C)SC=1C#N FZTJMMWGVZSSKJ-UHFFFAOYSA-N 0.000 claims 1
- OKEHURCMYKPVFW-UHFFFAOYSA-N 2-methoxythiophene Chemical compound COC1=CC=CS1 OKEHURCMYKPVFW-UHFFFAOYSA-N 0.000 claims 1
- SEXFQRKNXCUFRE-UHFFFAOYSA-N 3-dimethoxyphosphinothioyloxy-5-ethylsulfanylthiophene-2-carbonitrile Chemical compound CCSC1=CC(OP(=S)(OC)OC)=C(C#N)S1 SEXFQRKNXCUFRE-UHFFFAOYSA-N 0.000 claims 1
- 230000000895 acaricidal effect Effects 0.000 abstract description 4
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 150000003577 thiophenes Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 63
- -1 propylamino, isopropylamino, butylamino Chemical group 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 24
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 23
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 229910052700 potassium Inorganic materials 0.000 description 21
- 239000011591 potassium Substances 0.000 description 21
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 20
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 241000500891 Insecta Species 0.000 description 9
- 239000002917 insecticide Substances 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- FICQFRCPSFCFBY-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylidene]propanedinitrile Chemical compound CSC(SC)=C(C#N)C#N FICQFRCPSFCFBY-UHFFFAOYSA-N 0.000 description 6
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 6
- 239000000642 acaricide Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 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 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- BATLJJRWVYLNFT-UHFFFAOYSA-N 3-hydroxy-5-methoxythiophene-2-carbonitrile Chemical compound COC1=CC(O)=C(C#N)S1 BATLJJRWVYLNFT-UHFFFAOYSA-N 0.000 description 3
- UZDLWOZHCZOAIU-UHFFFAOYSA-N 3-hydroxy-5-methylthiophene-2-carbonitrile Chemical compound CC1=CC(O)=C(C#N)S1 UZDLWOZHCZOAIU-UHFFFAOYSA-N 0.000 description 3
- DHZOFWFPFXBMAO-UHFFFAOYSA-N 5-butoxy-3-hydroxythiophene-2-carbonitrile Chemical compound CCCCOC1=CC(O)=C(C#N)S1 DHZOFWFPFXBMAO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 230000009102 absorption Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229940022663 acetate Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- JKIAGGYDQZXBNO-UHFFFAOYSA-N 2-butoxythiophene Chemical compound CCCCOC1=CC=CS1 JKIAGGYDQZXBNO-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XGOQXIZBHMCULB-UHFFFAOYSA-N (2-cyano-5-propylthiophen-3-yl) dimethyl phosphate Chemical compound CCCC1=CC(OP(=O)(OC)OC)=C(C#N)S1 XGOQXIZBHMCULB-UHFFFAOYSA-N 0.000 description 1
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- IGJJUUQIJYEMTD-UHFFFAOYSA-N (5-butoxy-2-cyanothiophen-3-yl) dimethyl phosphate Chemical compound CCCCOC1=CC(OP(=O)(OC)OC)=C(C#N)S1 IGJJUUQIJYEMTD-UHFFFAOYSA-N 0.000 description 1
- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical compound C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 description 1
- CHZAMJVESILJGH-UHFFFAOYSA-N 3-[bis(2-cyanoethyl)phosphanyl]propanenitrile Chemical compound N#CCCP(CCC#N)CCC#N CHZAMJVESILJGH-UHFFFAOYSA-N 0.000 description 1
- QTIOPPCBTSWFOL-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-5-methylthiophene-2-carbonitrile Chemical compound CCOP(=S)(OCC)OC=1C=C(C)SC=1C#N QTIOPPCBTSWFOL-UHFFFAOYSA-N 0.000 description 1
- PNXNZEIJEXRZOL-UHFFFAOYSA-N 3-dimethoxyphosphinothioyloxy-5-phenylthiophene-2-carbonitrile Chemical compound S1C(C#N)=C(OP(=S)(OC)OC)C=C1C1=CC=CC=C1 PNXNZEIJEXRZOL-UHFFFAOYSA-N 0.000 description 1
- UPIREZQHLJTWOQ-UHFFFAOYSA-N 3-hydroxy-5-phenylthiophene-2-carbonitrile Chemical compound S1C(C#N)=C(O)C=C1C1=CC=CC=C1 UPIREZQHLJTWOQ-UHFFFAOYSA-N 0.000 description 1
- HQHGJRRZSVKWLE-UHFFFAOYSA-N 3-hydroxy-5-propylthiophene-2-carbonitrile Chemical compound CCCC1=CC(O)=C(C#N)S1 HQHGJRRZSVKWLE-UHFFFAOYSA-N 0.000 description 1
- BDCLDNALSPBWPQ-UHFFFAOYSA-M 3-oxohexanoate Chemical compound CCCC(=O)CC([O-])=O BDCLDNALSPBWPQ-UHFFFAOYSA-M 0.000 description 1
- JEVSLJKRRFGYFS-UHFFFAOYSA-N 5-ethylsulfanyl-3-hydroxythiophene-2-carbonitrile Chemical compound CCSC1=CC(O)=C(C#N)S1 JEVSLJKRRFGYFS-UHFFFAOYSA-N 0.000 description 1
- 241001600407 Aphis <genus> Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
- 101100172879 Caenorhabditis elegans sec-5 gene Proteins 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000244205 Panagrellus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 230000002506 adulticidal effect Effects 0.000 description 1
- OVXZVDMCQPLHIY-QXGOIDDHSA-L calcium;4-[[(2r)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]butanoate Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCCC([O-])=O OVXZVDMCQPLHIY-QXGOIDDHSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- KXMQPGJXTIKBSV-UHFFFAOYSA-N ctk0i0198 Chemical compound NP(O)(Cl)=S KXMQPGJXTIKBSV-UHFFFAOYSA-N 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- ZEUUVJSRINKECZ-UHFFFAOYSA-N ethanedithioic acid Chemical compound CC(S)=S ZEUUVJSRINKECZ-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002267 larvicidal agent Substances 0.000 description 1
- FELLHCNTGRGTIK-UHFFFAOYSA-N methyl 3-diethoxyphosphinothioyloxy-5-methylthiophene-2-carboxylate Chemical compound CCOP(=S)(OCC)OC=1C=C(C)SC=1C(=O)OC FELLHCNTGRGTIK-UHFFFAOYSA-N 0.000 description 1
- NNPLFTBGNUKNKL-UHFFFAOYSA-N methyl 3-dimethoxyphosphoryloxy-5-methoxythiophene-2-carboxylate Chemical compound COC(=O)C=1SC(OC)=CC=1OP(=O)(OC)OC NNPLFTBGNUKNKL-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- RUUFMHUAHUPZSS-UHFFFAOYSA-N oxido-oxo-sulfinophosphanium Chemical compound P(=O)(=O)S(=O)O RUUFMHUAHUPZSS-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- CHXZRHMQQRUVHF-UHFFFAOYSA-N thiophene A Natural products CC#CC1=CC=C(C#CC#CC=C)S1 CHXZRHMQQRUVHF-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7504628A FR2300768A1 (fr) | 1975-02-14 | 1975-02-14 | Nouveaux composes thiopeniques phosphoryles, procede de preparation et application comme pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1074795A true CA1074795A (en) | 1980-04-01 |
Family
ID=9151233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,098A Expired CA1074795A (en) | 1975-02-14 | 1976-02-05 | Process for the preparation of novel phosphorylated thiophenic substances |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS51105053A (tr) |
| BE (1) | BE838487A (tr) |
| BG (1) | BG25196A3 (tr) |
| BR (1) | BR7600876A (tr) |
| CA (1) | CA1074795A (tr) |
| CH (1) | CH610331A5 (tr) |
| DD (1) | DD125575A5 (tr) |
| DE (1) | DE2605649A1 (tr) |
| DK (1) | DK58376A (tr) |
| EG (1) | EG12442A (tr) |
| ES (1) | ES444618A1 (tr) |
| FR (1) | FR2300768A1 (tr) |
| GB (1) | GB1511413A (tr) |
| GR (1) | GR59269B (tr) |
| HU (1) | HU176606B (tr) |
| IL (1) | IL48857A (tr) |
| IT (1) | IT1053490B (tr) |
| NL (1) | NL7601489A (tr) |
| OA (1) | OA05248A (tr) |
| PH (1) | PH15203A (tr) |
| PL (1) | PL98486B1 (tr) |
| PT (1) | PT64795B (tr) |
| SU (1) | SU644360A3 (tr) |
| TR (1) | TR19251A (tr) |
| ZA (1) | ZA76709B (tr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831936A1 (de) * | 1978-07-20 | 1980-02-07 | Basf Ag | Thienylmethyl-phosphorsaeureester |
| JPS6058918B2 (ja) * | 1980-01-22 | 1985-12-23 | 宇部興産株式会社 | チオフエン誘導体および農園芸用殺菌剤 |
| US4454131A (en) * | 1982-04-30 | 1984-06-12 | Ube Industries, Ltd. | Thiophene derivatives |
| US8193372B2 (en) * | 2009-03-04 | 2012-06-05 | Idenix Pharmaceuticals, Inc. | Phosphothiophene and phosphothiazole HCV polymerase inhibitors |
-
1975
- 1975-02-14 FR FR7504628A patent/FR2300768A1/fr active Granted
-
1976
- 1976-01-16 IL IL48857A patent/IL48857A/xx unknown
- 1976-01-26 ES ES444618A patent/ES444618A1/es not_active Expired
- 1976-01-28 BG BG032211A patent/BG25196A3/xx unknown
- 1976-02-05 CA CA245,098A patent/CA1074795A/en not_active Expired
- 1976-02-06 ZA ZA760709A patent/ZA76709B/xx unknown
- 1976-02-09 PH PH18068A patent/PH15203A/en unknown
- 1976-02-10 SU SU762318651A patent/SU644360A3/ru active
- 1976-02-10 EG EG66/76A patent/EG12442A/xx active
- 1976-02-12 DD DD191215A patent/DD125575A5/xx unknown
- 1976-02-12 BE BE164261A patent/BE838487A/xx unknown
- 1976-02-12 DE DE19762605649 patent/DE2605649A1/de not_active Withdrawn
- 1976-02-12 BR BR7600876A patent/BR7600876A/pt unknown
- 1976-02-13 GR GR50050A patent/GR59269B/el unknown
- 1976-02-13 NL NL7601489A patent/NL7601489A/xx not_active Application Discontinuation
- 1976-02-13 CH CH181076A patent/CH610331A5/xx not_active IP Right Cessation
- 1976-02-13 TR TR19251A patent/TR19251A/tr unknown
- 1976-02-13 HU HU76RO878A patent/HU176606B/hu unknown
- 1976-02-13 PL PL1976187218A patent/PL98486B1/pl unknown
- 1976-02-13 GB GB5698/76A patent/GB1511413A/en not_active Expired
- 1976-02-13 DK DK58376*#A patent/DK58376A/da unknown
- 1976-02-13 JP JP51014121A patent/JPS51105053A/ja active Pending
- 1976-02-13 PT PT64795A patent/PT64795B/pt unknown
- 1976-02-13 IT IT48103/76A patent/IT1053490B/it active
- 1976-02-14 OA OA55742A patent/OA05248A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD125575A5 (tr) | 1977-05-04 |
| OA05248A (fr) | 1981-02-28 |
| ES444618A1 (es) | 1977-10-01 |
| IL48857A (en) | 1978-06-15 |
| ZA76709B (en) | 1977-03-30 |
| FR2300768A1 (fr) | 1976-09-10 |
| GR59269B (en) | 1977-12-05 |
| IT1053490B (it) | 1981-08-31 |
| PT64795B (fr) | 1978-02-06 |
| TR19251A (tr) | 1978-08-15 |
| EG12442A (en) | 1981-03-31 |
| PH15203A (en) | 1982-09-17 |
| JPS51105053A (tr) | 1976-09-17 |
| PL98486B1 (pl) | 1978-05-31 |
| NL7601489A (nl) | 1976-08-17 |
| FR2300768B1 (tr) | 1977-07-22 |
| BE838487A (fr) | 1976-08-12 |
| DE2605649A1 (de) | 1976-08-26 |
| AU1110476A (en) | 1977-08-18 |
| DK58376A (da) | 1976-08-15 |
| IL48857A0 (en) | 1976-03-31 |
| HU176606B (en) | 1981-03-28 |
| BR7600876A (pt) | 1976-09-14 |
| GB1511413A (en) | 1978-05-17 |
| SU644360A3 (ru) | 1979-01-25 |
| BG25196A3 (en) | 1978-08-10 |
| CH610331A5 (en) | 1979-04-12 |
| PT64795A (fr) | 1976-03-01 |
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