PL135350B1 - Method of obtaining novel pyretroides and insecticide and/or acaricide - Google Patents
Method of obtaining novel pyretroides and insecticide and/or acaricide Download PDFInfo
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- PL135350B1 PL135350B1 PL1979213760A PL21376079A PL135350B1 PL 135350 B1 PL135350 B1 PL 135350B1 PL 1979213760 A PL1979213760 A PL 1979213760A PL 21376079 A PL21376079 A PL 21376079A PL 135350 B1 PL135350 B1 PL 135350B1
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- 238000000034 method Methods 0.000 title claims description 28
- 230000000895 acaricidal effect Effects 0.000 title claims description 17
- 239000002917 insecticide Substances 0.000 title claims description 10
- 239000000642 acaricide Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 96
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 25
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 20
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 150000001266 acyl halides Chemical class 0.000 claims description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 48
- -1 esters of 2 Chemical compound 0.000 description 29
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- 239000000047 product Substances 0.000 description 20
- 230000000749 insecticidal effect Effects 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
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- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 5
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- 241000196324 Embryophyta Species 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
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- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical class O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 4
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical group C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical group Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20713/78A IT1095449B (it) | 1978-02-28 | 1978-02-28 | Nuovi piretroidi |
| IT2071478A IT1095450B (it) | 1978-02-28 | 1978-02-28 | Nuovi acidi ed esteri ciclopropancarbossilici |
| IT3131078A IT1160403B (it) | 1978-12-27 | 1978-12-27 | Processo per la sintesi di acidi ed esteri ciclopropancarbossilici |
| IT1970379A IT1166603B (it) | 1979-01-30 | 1979-01-30 | Piretroidi |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL213760A1 PL213760A1 (pl) | 1979-12-17 |
| PL135350B1 true PL135350B1 (pl) | 1985-10-31 |
Family
ID=27452781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1979213760A PL135350B1 (pl) | 1978-02-28 | 1979-02-27 | Method of obtaining novel pyretroides and insecticide and/or acaricide |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS54130537A (fr) |
| AR (1) | AR241108A1 (fr) |
| AU (1) | AU531296B2 (fr) |
| BE (1) | BE874515A (fr) |
| BG (3) | BG48921A3 (fr) |
| BR (1) | BR7901221A (fr) |
| CA (1) | CA1237439A (fr) |
| CH (1) | CH638485A5 (fr) |
| DD (2) | DD148767A5 (fr) |
| DE (1) | DE2907609A1 (fr) |
| DK (1) | DK161830C (fr) |
| ES (1) | ES478426A1 (fr) |
| FR (1) | FR2442826A1 (fr) |
| GB (1) | GB2015519B (fr) |
| GR (1) | GR72544B (fr) |
| HU (1) | HU185607B (fr) |
| IL (1) | IL56739A0 (fr) |
| IN (1) | IN150228B (fr) |
| KE (1) | KE3293A (fr) |
| LU (1) | LU80981A1 (fr) |
| MX (1) | MX5698E (fr) |
| NL (1) | NL7901460A (fr) |
| NO (2) | NO152582C (fr) |
| NZ (1) | NZ189791A (fr) |
| PL (1) | PL135350B1 (fr) |
| PT (1) | PT69283A (fr) |
| RO (1) | RO77772A (fr) |
| YU (1) | YU48279A (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831193A1 (de) * | 1978-07-15 | 1980-01-24 | Bayer Ag | Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide |
| EP0010874B1 (fr) * | 1978-10-27 | 1983-06-22 | Imperial Chemical Industries Plc | Procédé de séparation des isomères optiquement actifs des acides cyclopropane carboxyliques substitués; des sels amino des acides cyclopropane carboxyliques; acide cyclopropane carboxylique substitué |
| DE2919820A1 (de) * | 1979-05-16 | 1980-11-20 | Bayer Ag | Fluor-substituierte oxyalkenyl-cyclopropancarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
| EP0022608B1 (fr) * | 1979-07-13 | 1983-07-06 | Imperial Chemical Industries Plc | Procédé de préparation d'esters d'acides cyclopropane carboxyliques |
| IT1131883B (it) * | 1980-07-02 | 1986-06-25 | Montedison Spa | Processo per la sintesi stereoselettiva di ciclopropancarbossilati intermaedi per piretroidi |
| IL83606A (en) * | 1986-08-27 | 1992-03-29 | Montedison Spa | Esters of 3-(3-substituted-3,3-difluoro-1-propenyl)2,2-dimethyl-cyclopropanecarboxylic acid,their preparation and their use as insecticides and acaricides |
| DE3900275A1 (de) * | 1989-01-07 | 1990-07-12 | Basf Ag | Substituierte cyclopropancarbonsaeurepropargylester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| FR2687152A1 (fr) * | 1992-02-07 | 1993-08-13 | Roussel Uclaf | Nouveaux esters pyrethrinouides derives d'alcool furanique ou thiophenique, leur procede de preparation et leur application comme pesticides. |
| US6072074A (en) * | 1998-05-08 | 2000-06-06 | Sumitomo Chemical Company Limited | Process for producing 3-propynyl-2-2-dimethylcycloprophane-carboxylic acid and its lower akyl esters |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS515450B1 (fr) | 1971-06-29 | 1976-02-20 | ||
| DE2326077C2 (de) | 1972-05-25 | 1985-12-12 | National Research Development Corp., London | Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide |
| JPS5283720A (en) * | 1976-01-01 | 1977-07-12 | Kuraray Co Ltd | Substituted cyclopropanecarboxylic acid derivatives, and insecticides and acaricides containing a-substituted cyclopropanecarboxylic acid deri vatives |
| US4130655A (en) * | 1976-07-12 | 1978-12-19 | Ciba-Geigy Corporation | Pesticidal 2,2-dimethyl-3-isobutyl-cyclopropionates |
| DE2638356A1 (de) * | 1976-08-26 | 1978-03-02 | Bayer Ag | Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeureester |
| US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
| GB2008572B (en) * | 1977-11-28 | 1982-01-27 | Ici Ltd | Manufacture of esters |
| IN150399B (fr) * | 1978-01-20 | 1982-09-25 | Fmc Corp |
-
1979
- 1979-02-06 BG BG44136/79A patent/BG48921A3/xx unknown
- 1979-02-06 BG BG44135/79A patent/BG48333A3/xx unknown
- 1979-02-23 NL NL7901460A patent/NL7901460A/xx not_active Application Discontinuation
- 1979-02-23 NO NO790621A patent/NO152582C/no unknown
- 1979-02-23 DK DK080379A patent/DK161830C/da not_active IP Right Cessation
- 1979-02-23 BR BR7901221A patent/BR7901221A/pt unknown
- 1979-02-26 IL IL56739A patent/IL56739A0/xx not_active IP Right Cessation
- 1979-02-26 BG BG42659A patent/BG48931A3/xx unknown
- 1979-02-26 IN IN173/CAL/79A patent/IN150228B/en unknown
- 1979-02-26 PT PT69283A patent/PT69283A/pt unknown
- 1979-02-26 GR GR58472A patent/GR72544B/el unknown
- 1979-02-27 DE DE19792907609 patent/DE2907609A1/de active Granted
- 1979-02-27 CA CA000322525A patent/CA1237439A/fr not_active Expired
- 1979-02-27 PL PL1979213760A patent/PL135350B1/pl unknown
- 1979-02-27 DD DD79218658A patent/DD148767A5/de not_active IP Right Cessation
- 1979-02-27 AU AU44631/79A patent/AU531296B2/en not_active Expired
- 1979-02-27 FR FR7904952A patent/FR2442826A1/fr active Granted
- 1979-02-27 HU HU79MO1039A patent/HU185607B/hu unknown
- 1979-02-27 YU YU00482/79A patent/YU48279A/xx unknown
- 1979-02-27 ES ES478426A patent/ES478426A1/es not_active Expired
- 1979-02-27 GB GB7906851A patent/GB2015519B/en not_active Expired
- 1979-02-27 DD DD79211259A patent/DD142281A5/de not_active IP Right Cessation
- 1979-02-27 CH CH194279A patent/CH638485A5/it unknown
- 1979-02-28 AR AR275649A patent/AR241108A1/es active
- 1979-02-28 LU LU80981A patent/LU80981A1/fr unknown
- 1979-02-28 JP JP2204779A patent/JPS54130537A/ja active Granted
- 1979-02-28 NZ NZ189791A patent/NZ189791A/xx unknown
- 1979-02-28 RO RO79101065A patent/RO77772A/fr unknown
- 1979-02-28 BE BE0/193748A patent/BE874515A/fr not_active IP Right Cessation
- 1979-02-28 MX MX797764U patent/MX5698E/es unknown
- 1979-08-21 NO NO792716A patent/NO153098C/no unknown
-
1983
- 1983-06-08 KE KE3293A patent/KE3293A/xx unknown
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