CA1317220C - Pyrethroidal composition comprising more than one active ingredients - Google Patents
Pyrethroidal composition comprising more than one active ingredientsInfo
- Publication number
- CA1317220C CA1317220C CA000522189A CA522189A CA1317220C CA 1317220 C CA1317220 C CA 1317220C CA 000522189 A CA000522189 A CA 000522189A CA 522189 A CA522189 A CA 522189A CA 1317220 C CA1317220 C CA 1317220C
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- enantiomer
- pair
- active ingredient
- isomer
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 139
- 239000004480 active ingredient Substances 0.000 title claims abstract description 34
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 18
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 239000002728 pyrethroid Substances 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 5
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 239000012190 activator Substances 0.000 claims abstract description 4
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 4
- 239000003381 stabilizer Substances 0.000 claims abstract description 4
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- 239000003085 diluting agent Substances 0.000 claims abstract description 3
- 239000002270 dispersing agent Substances 0.000 claims abstract description 3
- 239000000945 filler Substances 0.000 claims abstract description 3
- 239000000080 wetting agent Substances 0.000 claims abstract description 3
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- 238000000034 method Methods 0.000 claims description 18
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- 241000607479 Yersinia pestis Species 0.000 claims description 7
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N TMDQ-1 Chemical group C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
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- 125000002723 alicyclic group Chemical group 0.000 claims 1
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- 125000004122 cyclic group Chemical group 0.000 claims 1
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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- 150000001447 alkali salts Chemical class 0.000 description 4
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- 235000019441 ethanol Nutrition 0.000 description 4
- 229960005235 piperonyl butoxide Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
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- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010033799 Paralysis Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 238000011109 contamination Methods 0.000 description 2
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- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
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- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 101100046831 Drosophila melanogaster Tpst gene Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000894243 Sericata Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241001222723 Sterna Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
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- 240000006365 Vitis vinifera Species 0.000 description 1
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- 230000002730 additional effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
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- 235000012907 honey Nutrition 0.000 description 1
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- 239000000543 intermediate Substances 0.000 description 1
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- 150000002500 ions 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
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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
- 230000002688 persistence Effects 0.000 description 1
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- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
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- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU8674A HU198373B (en) | 1986-01-08 | 1986-01-08 | Artropodicide composition containing trans-cipermetrin isomeres and process for producing the active components |
| HU74/86 | 1986-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1317220C true CA1317220C (en) | 1993-05-04 |
Family
ID=10947772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000522189A Expired - Fee Related CA1317220C (en) | 1986-01-08 | 1986-11-05 | Pyrethroidal composition comprising more than one active ingredients |
Country Status (10)
| Country | Link |
|---|---|
| CN (3) | CN1031972C (cs) |
| AP (2) | AP14A (cs) |
| AR (1) | AR244504A1 (cs) |
| CA (1) | CA1317220C (cs) |
| CS (2) | CS254993B2 (cs) |
| EG (2) | EG18452A (cs) |
| HU (1) | HU198373B (cs) |
| IL (1) | IL77624A (cs) |
| PL (4) | PL150680B1 (cs) |
| TR (2) | TR22871A (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1301304C (zh) * | 2004-02-26 | 2007-02-21 | 深圳市展辰达化工有限公司 | 硝基防白蚁防虫封闭底漆 |
| CN103819363A (zh) * | 2014-03-21 | 2014-05-28 | 中国农科院植保所廊坊农药中试厂 | 一种提高高效氯氰菊酯转位合成收率的方法 |
| WO2025007893A1 (zh) * | 2023-07-03 | 2025-01-09 | 山东康乔生物科技有限公司 | 亚硫酸酯类化合物及其制备方法与应用和组合物及防治害螨的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1048189B (it) * | 1973-08-15 | 1980-11-20 | Nat Res Dev | Perfezionamenti relativi a insetticidi |
| FR2375161A1 (fr) * | 1976-04-23 | 1978-07-21 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s) |
| US4261921A (en) * | 1979-06-06 | 1981-04-14 | Fmc Corporation | Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair |
| EP0107296B1 (en) * | 1982-10-18 | 1987-07-15 | Imperial Chemical Industries Plc | Insecticidal product and preparation thereof |
-
1986
- 1986-01-08 HU HU8674A patent/HU198373B/hu not_active IP Right Cessation
- 1986-01-16 IL IL77624A patent/IL77624A/xx not_active IP Right Cessation
- 1986-01-22 CS CS86480A patent/CS254993B2/cs not_active IP Right Cessation
- 1986-01-22 CS CS86481A patent/CS254994B2/cs not_active IP Right Cessation
- 1986-02-02 EG EG50/86A patent/EG18452A/xx active
- 1986-02-03 PL PL1986269466A patent/PL150680B1/pl unknown
- 1986-02-03 PL PL1986257772A patent/PL151661B1/pl unknown
- 1986-02-04 EG EG55/86A patent/EG18336A/xx active
- 1986-02-04 PL PL1986267524A patent/PL149799B1/pl unknown
- 1986-02-04 PL PL1986257782A patent/PL153005B1/pl unknown
- 1986-02-26 AP APAP/P/1986/000024A patent/AP14A/en active
- 1986-02-26 AP APAP/P/1986/000023A patent/AP13A/en active
- 1986-03-07 CN CN90109426A patent/CN1031972C/zh not_active Expired - Lifetime
- 1986-03-07 CN CN86101357A patent/CN1015709B/zh not_active Expired
- 1986-03-07 CN CN86101380A patent/CN1031996C/zh not_active Expired - Lifetime
- 1986-05-05 TR TR227/86A patent/TR22871A/xx unknown
- 1986-05-05 TR TR24355A patent/TR22867A/xx unknown
- 1986-11-05 CA CA000522189A patent/CA1317220C/en not_active Expired - Fee Related
-
1988
- 1988-02-27 AR AR88303240A patent/AR244504A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| CN86101380A (zh) | 1987-07-15 |
| CS48086A2 (en) | 1987-06-11 |
| PL257772A1 (en) | 1988-04-28 |
| PL257782A1 (en) | 1988-01-07 |
| AP8600023A0 (en) | 1986-02-01 |
| PL149799B1 (en) | 1990-03-31 |
| PL153005B1 (en) | 1991-02-28 |
| HU198373B (en) | 1989-10-30 |
| TR22871A (tr) | 1988-09-23 |
| CS254993B2 (en) | 1988-02-15 |
| PL150680B1 (en) | 1990-06-30 |
| AP13A (en) | 1988-03-08 |
| EG18336A (en) | 1993-06-30 |
| PL151661B1 (en) | 1990-09-28 |
| CN1031996C (zh) | 1996-06-12 |
| HUT41962A (en) | 1987-06-29 |
| IL77624A (en) | 1990-12-23 |
| AR244504A1 (es) | 1993-11-30 |
| TR22867A (tr) | 1988-09-19 |
| CN1050810A (zh) | 1991-04-24 |
| CN1031972C (zh) | 1996-06-12 |
| CN86101357A (zh) | 1987-07-15 |
| PL267524A1 (en) | 1988-05-26 |
| EG18452A (en) | 1993-04-30 |
| AP14A (en) | 1988-03-08 |
| AP8600024A0 (en) | 1986-02-01 |
| PL269466A1 (en) | 1988-12-22 |
| CN1015709B (zh) | 1992-03-04 |
| CS254994B2 (en) | 1988-02-15 |
| CS48186A2 (en) | 1987-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |