HU184523B - Insecticide compositions and process for preparing oxiimino-substituted-cyclopropane-carboxylic acid esters applicable as the active substances thereof - Google Patents
Insecticide compositions and process for preparing oxiimino-substituted-cyclopropane-carboxylic acid esters applicable as the active substances thereof Download PDFInfo
- Publication number
- HU184523B HU184523B HU79SE1940A HUSE001940A HU184523B HU 184523 B HU184523 B HU 184523B HU 79SE1940 A HU79SE1940 A HU 79SE1940A HU SE001940 A HUSE001940 A HU SE001940A HU 184523 B HU184523 B HU 184523B
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- Hungary
- Prior art keywords
- cis
- formula
- compounds
- phenoxybenzyl
- carbon atoms
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 39
- 239000002917 insecticide Substances 0.000 title claims description 6
- 239000013543 active substance Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- -1 aluminum silicates Chemical class 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 73
- 150000002148 esters Chemical class 0.000 claims description 41
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 8
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- 229910052801 chlorine Inorganic materials 0.000 claims description 7
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- 239000000194 fatty acid Substances 0.000 claims description 7
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
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- 125000000129 anionic group Chemical group 0.000 claims description 4
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
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- 239000011734 sodium Substances 0.000 claims description 3
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 1
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- 230000000361 pesticidal effect Effects 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 12
- 239000000543 intermediate Substances 0.000 abstract description 9
- 241000238631 Hexapoda Species 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- 150000004820 halides Chemical class 0.000 abstract description 5
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 abstract description 3
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 abstract description 2
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002728 pyrethroid Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
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- 238000012360 testing method Methods 0.000 description 12
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- 230000001988 toxicity Effects 0.000 description 11
- 231100000419 toxicity Toxicity 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 9
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- 235000019341 magnesium sulphate Nutrition 0.000 description 6
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JZAVZQOLBHZEGQ-UHFFFAOYSA-N (3-phenoxyphenyl)methyl cyclopropanecarboxylate Chemical compound C1CC1C(=O)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 JZAVZQOLBHZEGQ-UHFFFAOYSA-N 0.000 description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical class 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 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
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- 239000004834 spray adhesive Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- B24B23/00—Portable grinding machines, e.g. hand-guided; Accessories therefor
- B24B23/02—Portable grinding machines, e.g. hand-guided; Accessories therefor with rotating grinding tools; Accessories therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25F—COMBINATION OR MULTI-PURPOSE TOOLS NOT OTHERWISE PROVIDED FOR; DETAILS OR COMPONENTS OF PORTABLE POWER-DRIVEN TOOLS NOT PARTICULARLY RELATED TO THE OPERATIONS PERFORMED AND NOT OTHERWISE PROVIDED FOR
- B25F5/00—Details or components of portable power-driven tools not particularly related to the operations performed and not otherwise provided for
- B25F5/008—Cooling means
Landscapes
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Valve Device For Special Equipments (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Fluid-Driven Valves (AREA)
- Detergent Compositions (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91174378A | 1978-06-02 | 1978-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184523B true HU184523B (en) | 1984-09-28 |
Family
ID=25430781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79SE1940A HU184523B (en) | 1978-06-02 | 1979-05-31 | Insecticide compositions and process for preparing oxiimino-substituted-cyclopropane-carboxylic acid esters applicable as the active substances thereof |
Country Status (20)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4219565A (en) * | 1979-06-26 | 1980-08-26 | Shell Oil Company | Oxyimino-substituted cyclopropanecarboxylate pesticides |
| 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 |
| US4439446A (en) * | 1981-12-21 | 1984-03-27 | Shell Oil Company | Fluorine-containing oxyiminocyclopropanecarboxylates |
| ZA829332B (en) * | 1981-12-21 | 1983-09-28 | Shell Res Ltd | Fluorophenoxybenzyl esters, their preparation and use as pesticides |
| US4584304A (en) * | 1984-06-08 | 1986-04-22 | Shell Oil Company | 2-pyridinylmethyl oxyiminocyclopropanecarboxylates as pesticides |
| AU754206B2 (en) * | 1998-06-09 | 2002-11-07 | Sumitomo Chemical Company, Limited | Ester compounds |
| JP2002020209A (ja) * | 2000-07-06 | 2002-01-23 | Sumitomo Chem Co Ltd | エステル化合物を含有する蚊の防除剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1410080A (en) * | 1972-12-21 | 1975-10-15 | Nat Res Dev | Oxime derivatives of 2,2-dimethyl-3-formyl cyclopropane carboxylic acid and their use as insecticides |
| JPS5511006B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-05-07 | 1980-03-21 | ||
| IE41614B1 (en) * | 1973-08-15 | 1980-02-13 | Nat Res Dev | Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides |
-
1979
- 1979-04-26 DK DK173679A patent/DK158037C/da active IP Right Grant
- 1979-05-02 CA CA000326805A patent/CA1140141A/en not_active Expired
- 1979-05-23 EP EP79200256A patent/EP0005882B1/en not_active Expired
- 1979-05-23 DE DE7979200256T patent/DE2965606D1/de not_active Expired
- 1979-05-23 AT AT79200256T patent/ATE3713T1/de not_active IP Right Cessation
- 1979-05-30 ZA ZA792695A patent/ZA792695B/xx unknown
- 1979-05-31 DD DD79213322A patent/DD144504A5/de unknown
- 1979-05-31 CS CS793762A patent/CS210690B2/cs unknown
- 1979-05-31 IL IL57453A patent/IL57453A0/xx not_active IP Right Cessation
- 1979-05-31 PL PL21599679A patent/PL215996A1/xx unknown
- 1979-05-31 BR BR7903428A patent/BR7903428A/pt unknown
- 1979-05-31 PH PH22597A patent/PH16772A/en unknown
- 1979-05-31 YU YU01289/79A patent/YU128979A/xx unknown
- 1979-05-31 AU AU47633/79A patent/AU527266B2/en not_active Expired
- 1979-05-31 JP JP6691579A patent/JPS54160343A/ja active Pending
- 1979-05-31 TR TR21275A patent/TR21275A/xx unknown
- 1979-05-31 ES ES481127A patent/ES481127A1/es not_active Expired
- 1979-05-31 HU HU79SE1940A patent/HU184523B/hu unknown
- 1979-06-02 OA OA56821A patent/OA06268A/xx unknown
- 1979-08-08 IE IE1068/79A patent/IE48154B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL215996A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-11 |
| ATE3713T1 (de) | 1983-06-15 |
| OA06268A (fr) | 1981-06-30 |
| ES481127A1 (es) | 1980-02-01 |
| DK158037B (da) | 1990-03-19 |
| IL57453A0 (en) | 1979-09-30 |
| AU527266B2 (en) | 1983-02-24 |
| CA1140141A (en) | 1983-01-25 |
| DK173679A (da) | 1979-12-04 |
| DK158037C (da) | 1990-08-13 |
| ZA792695B (en) | 1980-06-25 |
| EP0005882B1 (en) | 1983-06-08 |
| BR7903428A (pt) | 1980-01-15 |
| DE2965606D1 (en) | 1983-07-14 |
| DD144504A5 (de) | 1980-10-22 |
| EP0005882A1 (en) | 1979-12-12 |
| TR21275A (tr) | 1984-03-15 |
| IE791068L (en) | 1979-12-02 |
| JPS54160343A (en) | 1979-12-19 |
| IE48154B1 (en) | 1984-10-17 |
| YU128979A (en) | 1983-12-31 |
| PH16772A (en) | 1984-02-22 |
| AU4763379A (en) | 1979-12-06 |
| CS210690B2 (en) | 1982-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |