IE48154B1 - A method of combating acarine pests by means of oxyimino-substituted cyclopropanecarboxylate esters,z-isomers of certain such esters - Google Patents
A method of combating acarine pests by means of oxyimino-substituted cyclopropanecarboxylate esters,z-isomers of certain such estersInfo
- Publication number
- IE48154B1 IE48154B1 IE1068/79A IE106879A IE48154B1 IE 48154 B1 IE48154 B1 IE 48154B1 IE 1068/79 A IE1068/79 A IE 1068/79A IE 106879 A IE106879 A IE 106879A IE 48154 B1 IE48154 B1 IE 48154B1
- Authority
- IE
- Ireland
- Prior art keywords
- group containing
- carbon atoms
- esters
- cis
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 241000607479 Yersinia pestis Species 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title description 33
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- -1 cyclopropanecarboxylate ester Chemical class 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 22
- 230000000361 pesticidal effect Effects 0.000 abstract description 13
- 150000004820 halides Chemical class 0.000 abstract description 10
- 241000238631 Hexapoda Species 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 5
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- 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
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- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 35
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- 150000002923 oximes Chemical group 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
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- 239000012071 phase Substances 0.000 description 11
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 10
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- 230000001988 toxicity Effects 0.000 description 10
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- 241000255967 Helicoverpa zea Species 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
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- 238000005481 NMR spectroscopy Methods 0.000 description 5
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- 239000003995 emulsifying agent Substances 0.000 description 5
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- 239000000654 additive Substances 0.000 description 4
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- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
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- 125000000262 haloalkenyl group Chemical group 0.000 description 1
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- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
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- 210000004080 milk Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000000025 natural resin Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- WOXGREIMSJFDPG-UHFFFAOYSA-N o-(2-methylpropyl)hydroxylamine;hydrochloride Chemical compound Cl.CC(C)CON WOXGREIMSJFDPG-UHFFFAOYSA-N 0.000 description 1
- HMMFZNBOQJOULD-UHFFFAOYSA-N o-(cyclopropylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1CC1 HMMFZNBOQJOULD-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 229940086065 potassium hydrogentartrate Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound 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
- 229940070846 pyrethrins Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax 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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Detergent Compositions (AREA)
- Valve Device For Special Equipments (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Fluid-Driven Valves (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 (2)
| Publication Number | Publication Date |
|---|---|
| IE791068L IE791068L (en) | 1979-12-02 |
| IE48154B1 true IE48154B1 (en) | 1984-10-17 |
Family
ID=25430781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1068/79A IE48154B1 (en) | 1978-06-02 | 1979-08-08 | A method of combating acarine pests by means of oxyimino-substituted cyclopropanecarboxylate esters,z-isomers of certain such esters |
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 | ||
| NL178590C (nl) * | 1973-08-15 | 1986-04-16 | Nat Res Dev | Werkwijze voor het bereiden van een insecticide preparaat; werkwijze voor het bereiden van een synthetisch pyrethroide. |
-
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 DE DE7979200256T patent/DE2965606D1/de not_active Expired
- 1979-05-23 AT AT79200256T patent/ATE3713T1/de not_active IP Right Cessation
- 1979-05-23 EP EP79200256A patent/EP0005882B1/en not_active Expired
- 1979-05-30 ZA ZA792695A patent/ZA792695B/xx unknown
- 1979-05-31 DD DD79213322A patent/DD144504A5/de unknown
- 1979-05-31 TR TR21275A patent/TR21275A/xx unknown
- 1979-05-31 BR BR7903428A patent/BR7903428A/pt unknown
- 1979-05-31 CS CS793762A patent/CS210690B2/cs unknown
- 1979-05-31 JP JP6691579A patent/JPS54160343A/ja active Pending
- 1979-05-31 PL PL21599679A patent/PL215996A1/xx unknown
- 1979-05-31 AU AU47633/79A patent/AU527266B2/en not_active Expired
- 1979-05-31 IL IL57453A patent/IL57453A0/xx not_active IP Right Cessation
- 1979-05-31 ES ES481127A patent/ES481127A1/es not_active Expired
- 1979-05-31 HU HU79SE1940A patent/HU184523B/hu unknown
- 1979-05-31 PH PH22597A patent/PH16772A/en unknown
- 1979-05-31 YU YU01289/79A patent/YU128979A/xx 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 |
|---|---|
| DK158037C (da) | 1990-08-13 |
| CS210690B2 (en) | 1982-01-29 |
| DK158037B (da) | 1990-03-19 |
| IL57453A0 (en) | 1979-09-30 |
| YU128979A (en) | 1983-12-31 |
| IE791068L (en) | 1979-12-02 |
| EP0005882B1 (en) | 1983-06-08 |
| AU4763379A (en) | 1979-12-06 |
| DK173679A (da) | 1979-12-04 |
| OA06268A (fr) | 1981-06-30 |
| TR21275A (tr) | 1984-03-15 |
| ATE3713T1 (de) | 1983-06-15 |
| PL215996A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-11 |
| HU184523B (en) | 1984-09-28 |
| ZA792695B (en) | 1980-06-25 |
| AU527266B2 (en) | 1983-02-24 |
| CA1140141A (en) | 1983-01-25 |
| JPS54160343A (en) | 1979-12-19 |
| DD144504A5 (de) | 1980-10-22 |
| BR7903428A (pt) | 1980-01-15 |
| EP0005882A1 (en) | 1979-12-12 |
| ES481127A1 (es) | 1980-02-01 |
| PH16772A (en) | 1984-02-22 |
| DE2965606D1 (en) | 1983-07-14 |
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| MM4A | Patent lapsed |