CH643540A5 - Nuovi piretroidi e loro processo di sintesi. - Google Patents
Nuovi piretroidi e loro processo di sintesi. Download PDFInfo
- Publication number
- CH643540A5 CH643540A5 CH173780A CH173780A CH643540A5 CH 643540 A5 CH643540 A5 CH 643540A5 CH 173780 A CH173780 A CH 173780A CH 173780 A CH173780 A CH 173780A CH 643540 A5 CH643540 A5 CH 643540A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- ester
- acid
- formula
- cyan
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 230000015572 biosynthetic process Effects 0.000 title claims description 6
- 238000003786 synthesis reaction Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 19
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 230000000749 insecticidal effect Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- -1 3-phenoxybenzyl Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 125000004494 ethyl ester group Chemical group 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 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 description 8
- 239000000243 solution Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 150000001263 acyl chlorides Chemical class 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000004460 Tanacetum coccineum Species 0.000 description 3
- ROVGZAWFACYCSP-MQBLHHJJSA-N [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 Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229940015367 pyrethrum Drugs 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241000254022 Locusta migratoria Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 229960000490 permethrin Drugs 0.000 description 2
- 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 2
- 239000000843 powder Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical group CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- IMAYQBJEBRMWLC-UHFFFAOYSA-N C(C)C1=C(C(NCl)(CC)CC)C=CC=C1 Chemical compound C(C)C1=C(C(NCl)(CC)CC)C=CC=C1 IMAYQBJEBRMWLC-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical class CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- 241000258915 Leptinotarsa Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000254023 Locusta Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000256626 Pterygota <winged insects> Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000007682 dermal toxicity Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000438 skin toxicity Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20853/79A IT1166681B (it) | 1979-03-09 | 1979-03-09 | Piretroidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643540A5 true CH643540A5 (it) | 1984-06-15 |
Family
ID=11173041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH173780A CH643540A5 (it) | 1979-03-09 | 1980-03-05 | Nuovi piretroidi e loro processo di sintesi. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4285969A (enExample) |
| JP (1) | JPS55127361A (enExample) |
| AU (1) | AU540138B2 (enExample) |
| BE (1) | BE882138A (enExample) |
| BR (1) | BR8001350A (enExample) |
| CA (1) | CA1145768A (enExample) |
| CH (1) | CH643540A5 (enExample) |
| DD (2) | DD149895A5 (enExample) |
| DE (1) | DE3008670A1 (enExample) |
| EG (1) | EG14376A (enExample) |
| ES (1) | ES8104787A1 (enExample) |
| FR (1) | FR2450812A1 (enExample) |
| GB (1) | GB2044769B (enExample) |
| IL (1) | IL59522A (enExample) |
| IT (1) | IT1166681B (enExample) |
| NL (1) | NL8001267A (enExample) |
| ZA (1) | ZA801296B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2471369A1 (fr) * | 1979-12-17 | 1981-06-19 | Roussel Uclaf | Nouvelles imines, derivant d'esters d'acides formyl cyclopropane carboxyliques, leur procede de preparation et leur application a la preparation d'esters insecticides |
| AU615879B2 (en) * | 1986-08-27 | 1991-10-17 | Montedison S.P.A. | Derivatives of 2,2-dimethyl-cyclopropanecarboxylic acid |
| US5238957A (en) * | 1988-07-07 | 1993-08-24 | Presidenza Del Consiglio Dei Ministri-Uffico Del Ministro Per Il Coordinamento Delle Iniziative Per La Ricerca Scientifica E Tecnologica | Esters of 2,2-dimethyl-cyclopropane-carboxylic acid |
| US9406561B2 (en) * | 2009-04-20 | 2016-08-02 | International Business Machines Corporation | Three dimensional integrated circuit integration using dielectric bonding first and through via formation last |
| US7939369B2 (en) | 2009-05-14 | 2011-05-10 | International Business Machines Corporation | 3D integration structure and method using bonded metal planes |
| US8563403B1 (en) | 2012-06-27 | 2013-10-22 | International Business Machines Corporation | Three dimensional integrated circuit integration using alignment via/dielectric bonding first and through via formation last |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248646A (en) * | 1975-10-16 | 1977-04-18 | Sankyo Co Ltd | Insecticides containing novel cyclopropanecarboxylic acid esters and t heir preparation |
| DE2647368A1 (de) * | 1975-10-23 | 1977-05-05 | Ciba Geigy Ag | Alpha-(1-pyrrolyl)-carbonsaeure-3- phenoxy-benzylester, verfahren zu ihrer herstellung und ihre verwendung |
| JPS5412348A (en) * | 1977-06-17 | 1979-01-30 | Sumitomo Chem Co Ltd | Cyclopropane carboxylic acid esters, their preparation, and insecticides and acaricides comprising them as active constituents |
| DE2730515A1 (de) * | 1977-07-06 | 1979-01-18 | Bayer Ag | Substituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| US4200644A (en) * | 1978-01-26 | 1980-04-29 | Fmc Corporation | Arylthiovinylcyclopropanecarboxylate insecticides |
-
1979
- 1979-03-09 IT IT20853/79A patent/IT1166681B/it active
-
1980
- 1980-03-03 NL NL8001267A patent/NL8001267A/nl not_active Application Discontinuation
- 1980-03-04 IL IL59522A patent/IL59522A/xx unknown
- 1980-03-04 AU AU56098/80A patent/AU540138B2/en not_active Ceased
- 1980-03-04 US US06/127,118 patent/US4285969A/en not_active Expired - Lifetime
- 1980-03-05 ZA ZA00801296A patent/ZA801296B/xx unknown
- 1980-03-05 CH CH173780A patent/CH643540A5/it not_active IP Right Cessation
- 1980-03-06 DE DE19803008670 patent/DE3008670A1/de not_active Withdrawn
- 1980-03-06 BR BR8001350A patent/BR8001350A/pt unknown
- 1980-03-07 DD DD80219529A patent/DD149895A5/de unknown
- 1980-03-07 JP JP2822980A patent/JPS55127361A/ja active Pending
- 1980-03-07 FR FR8005207A patent/FR2450812A1/fr active Granted
- 1980-03-07 BE BE0/199723A patent/BE882138A/fr not_active IP Right Cessation
- 1980-03-07 DD DD80229947A patent/DD158548A5/de unknown
- 1980-03-07 CA CA000347286A patent/CA1145768A/en not_active Expired
- 1980-03-07 GB GB8007790A patent/GB2044769B/en not_active Expired
- 1980-03-08 ES ES489355A patent/ES8104787A1/es not_active Expired
- 1980-03-09 EG EG134/80A patent/EG14376A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| AU5609880A (en) | 1980-09-11 |
| IT1166681B (it) | 1987-05-06 |
| NL8001267A (nl) | 1980-09-11 |
| GB2044769B (en) | 1983-05-11 |
| FR2450812A1 (fr) | 1980-10-03 |
| US4285969A (en) | 1981-08-25 |
| IL59522A (en) | 1983-09-30 |
| BE882138A (fr) | 1980-09-08 |
| DE3008670A1 (de) | 1980-09-11 |
| IL59522A0 (en) | 1980-06-30 |
| GB2044769A (en) | 1980-10-22 |
| AU540138B2 (en) | 1984-11-01 |
| FR2450812B1 (enExample) | 1983-11-10 |
| DD149895A5 (de) | 1981-08-05 |
| ES489355A0 (es) | 1981-04-16 |
| BR8001350A (pt) | 1980-11-11 |
| IT7920853A0 (it) | 1979-03-09 |
| EG14376A (en) | 1983-12-31 |
| CA1145768A (en) | 1983-05-03 |
| ES8104787A1 (es) | 1981-04-16 |
| JPS55127361A (en) | 1980-10-02 |
| ZA801296B (en) | 1981-02-25 |
| DD158548A5 (de) | 1983-01-19 |
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