CA1079285A - Preparation de n-benzolyl n'-pyridyloxyphenyluree - Google Patents
Preparation de n-benzolyl n'-pyridyloxyphenylureeInfo
- Publication number
- CA1079285A CA1079285A CA301,811A CA301811A CA1079285A CA 1079285 A CA1079285 A CA 1079285A CA 301811 A CA301811 A CA 301811A CA 1079285 A CA1079285 A CA 1079285A
- Authority
- CA
- Canada
- Prior art keywords
- urea
- phenyl
- oxy
- halogen atom
- chloro
- 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
- LUBJCRLGQSPQNN-UHFFFAOYSA-N Z-phenylurea Natural products NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 33
- 241000238631 Hexapoda Species 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000000266 injurious effect Effects 0.000 claims abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- ZYRQUYCVZFSMPZ-UHFFFAOYSA-N n-phenyl-n-(pyridin-2-yloxycarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(C=1C=CC=CC=1)C(=O)NOC1=CC=CC=N1 ZYRQUYCVZFSMPZ-UHFFFAOYSA-N 0.000 claims abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 85
- 239000004202 carbamide Substances 0.000 claims description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- -1 pyridyloxy aniline Chemical compound 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 abstract description 6
- 235000013877 carbamide Nutrition 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 230000000749 insecticidal effect Effects 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 241000426497 Chilo suppressalis Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000721703 Lymantria dispar Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000254112 Tribolium confusum Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000633318 Culex pipiens molestus Species 0.000 description 2
- 241000255967 Helicoverpa zea Species 0.000 description 2
- 241001531327 Hyphantria cunea Species 0.000 description 2
- 241000555303 Mamestra brassicae Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- 241000254234 Xyeloidea Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- RZMVHCYCUAKRMM-UHFFFAOYSA-N 2-methylbenzoyl isocyanate Chemical compound CC1=CC=CC=C1C(=O)N=C=O RZMVHCYCUAKRMM-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000144210 Culex pipiens pallens Species 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 241000933192 Papilio xuthus Species 0.000 description 1
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- 241000227425 Pieris rapae crucivora Species 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP53012215A JPS5823871B2 (ja) | 1978-02-06 | 1978-02-06 | Ｎ↓−ピリジルオキシフエニルウレア系化合物及びそれらを含有する殺虫剤 |
| JP2982878A JPS54125677A (en) | 1978-03-17 | 1978-03-17 | N-benzoyl-n'-pyridyloxyphenylurea compound,its preparation,and insecticide containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079285A true CA1079285A (fr) | 1980-06-10 |
Family
ID=26347785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA301,811A Expired CA1079285A (fr) | 1978-02-06 | 1978-04-24 | Preparation de n-benzolyl n'-pyridyloxyphenyluree |
Country Status (7)
| Country | Link |
|---|---|
| CA (1) | CA1079285A (fr) |
| DK (1) | DK155664C (fr) |
| FI (1) | FI70211C (fr) |
| NL (1) | NL189293C (fr) |
| NO (1) | NO149429C (fr) |
| PH (1) | PH16906A (fr) |
| SE (1) | SE430249B (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4904668A (en) * | 1986-09-29 | 1990-02-27 | Ishihara Sangyo Kaisha Ltd. | Benzoyl urea compound |
| US7084138B2 (en) | 2000-09-05 | 2006-08-01 | Bayer Cropscience Ag | Active ingredient combinations with insecticidal and acaricidal properties |
| US8828907B2 (en) | 2009-03-25 | 2014-09-09 | Bayer Cropscience Ag | Active ingredient combinations having insecticidal and acaricidal properties |
| CN105010371A (zh) * | 2015-02-12 | 2015-11-04 | 四川利尔作物科学有限公司 | 杀虫组合物及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK47476C (da) * | 1930-07-21 | 1933-06-26 | Aga Baltic Radio Ab | Anordning ved Radiomodtagere. |
| US3931201A (en) * | 1974-01-22 | 1976-01-06 | The Dow Chemical Company | Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives |
| GB1460419A (en) * | 1975-02-06 | 1977-01-06 | Bayer Ag | Benzoylureido-diphenyl ethers and their use as insecticides |
-
1978
- 1978-04-21 NL NLAANVRAGE7804264,A patent/NL189293C/xx not_active IP Right Cessation
- 1978-04-24 CA CA301,811A patent/CA1079285A/fr not_active Expired
- 1978-04-27 FI FI781315A patent/FI70211C/fi not_active IP Right Cessation
- 1978-04-28 DK DK187078A patent/DK155664C/da not_active IP Right Cessation
- 1978-04-28 PH PH21081A patent/PH16906A/en unknown
- 1978-04-28 SE SE7804972A patent/SE430249B/sv not_active IP Right Cessation
- 1978-04-28 NO NO781516A patent/NO149429C/no unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4904668A (en) * | 1986-09-29 | 1990-02-27 | Ishihara Sangyo Kaisha Ltd. | Benzoyl urea compound |
| US7084138B2 (en) | 2000-09-05 | 2006-08-01 | Bayer Cropscience Ag | Active ingredient combinations with insecticidal and acaricidal properties |
| US8828907B2 (en) | 2009-03-25 | 2014-09-09 | Bayer Cropscience Ag | Active ingredient combinations having insecticidal and acaricidal properties |
| CN105010371A (zh) * | 2015-02-12 | 2015-11-04 | 四川利尔作物科学有限公司 | 杀虫组合物及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| PH16906A (en) | 1984-04-10 |
| NO149429B (no) | 1984-01-09 |
| NL189293B (nl) | 1992-10-01 |
| DK155664C (da) | 1989-10-09 |
| SE7804972L (sv) | 1979-08-07 |
| DK155664B (da) | 1989-05-01 |
| FI70211C (fi) | 1986-09-15 |
| NO781516L (no) | 1979-08-07 |
| DK187078A (da) | 1979-08-07 |
| NL189293C (nl) | 1993-03-01 |
| NL7804264A (nl) | 1979-08-08 |
| NO149429C (no) | 1984-04-25 |
| SE430249B (sv) | 1983-10-31 |
| FI70211B (fi) | 1986-02-28 |
| FI781315A7 (fi) | 1979-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |