NZ245581A - 1,2,4-triazolo[1,5-a]pyrimidine derivatives and fungicidal compositions - Google Patents
1,2,4-triazolo[1,5-a]pyrimidine derivatives and fungicidal compositionsInfo
- Publication number
- NZ245581A NZ245581A NZ245581A NZ24558192A NZ245581A NZ 245581 A NZ245581 A NZ 245581A NZ 245581 A NZ245581 A NZ 245581A NZ 24558192 A NZ24558192 A NZ 24558192A NZ 245581 A NZ245581 A NZ 245581A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- group
- formula
- phenyl
- alkyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 40
- 230000000855 fungicidal effect Effects 0.000 title claims description 21
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 title description 2
- 239000000460 chlorine Substances 0.000 claims abstract description 95
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- -1 alkadienyl Chemical group 0.000 claims description 192
- 150000001875 compounds Chemical class 0.000 claims description 131
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 241000233866 Fungi Species 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Chemical group 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 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- 101100450129 Caenorhabditis elegans hal-3 gene Proteins 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 description 81
- 241000196324 Embryophyta Species 0.000 description 66
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 62
- 230000000694 effects Effects 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000007921 spray Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 201000010099 disease Diseases 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 241000209140 Triticum Species 0.000 description 12
- 238000000338 in vitro Methods 0.000 description 12
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- 239000007900 aqueous suspension Substances 0.000 description 10
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- 240000005979 Hordeum vulgare Species 0.000 description 8
- 235000007340 Hordeum vulgare Nutrition 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
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- 229920001817 Agar Polymers 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000813090 Rhizoctonia solani Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 6
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 241000736122 Parastagonospora nodorum Species 0.000 description 5
- 229920001213 Polysorbate 20 Polymers 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP91122422 | 1991-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ245581A true NZ245581A (en) | 1995-07-26 |
Family
ID=8207489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ245581A NZ245581A (en) | 1991-12-30 | 1992-12-23 | 1,2,4-triazolo[1,5-a]pyrimidine derivatives and fungicidal compositions |
Country Status (21)
| Country | Link |
|---|---|
| EP (2) | EP0782997B1 (enExample) |
| JP (1) | JP3347170B2 (enExample) |
| KR (1) | KR100271913B1 (enExample) |
| CN (2) | CN1033643C (enExample) |
| AT (2) | ATE159256T1 (enExample) |
| AU (1) | AU667204B2 (enExample) |
| BR (1) | BR9205172A (enExample) |
| CA (1) | CA2086404C (enExample) |
| DE (2) | DE69230977T2 (enExample) |
| DK (2) | DK0782997T3 (enExample) |
| ES (2) | ES2108727T3 (enExample) |
| GR (2) | GR3025920T3 (enExample) |
| HU (1) | HU217349B (enExample) |
| IL (1) | IL104244A (enExample) |
| NZ (1) | NZ245581A (enExample) |
| PL (2) | PL174047B1 (enExample) |
| PT (1) | PT782997E (enExample) |
| RU (1) | RU2089552C1 (enExample) |
| SG (1) | SG47563A1 (enExample) |
| TW (1) | TW224044B (enExample) |
| ZA (1) | ZA9210043B (enExample) |
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| IL137617A0 (en) * | 1998-02-11 | 2001-07-24 | American Cyanamid Co | Fungicidal 7-akyl-triazolopyrimidines |
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| PE20001145A1 (es) * | 1998-09-10 | 2000-10-25 | American Cyanamid Co | Mezclas fungicidas |
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| TWI229674B (en) * | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
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| MY179926A (en) | 2003-12-08 | 2020-11-19 | Wyeth Corp | Process for the preparation of tubulin inhibitors |
| EA200601108A1 (ru) * | 2003-12-18 | 2006-12-29 | Басф Акциенгезельшафт | 6-(2-галогенфенил)триазолопиримидины, способ их получения и их применение для борьбы с патогенными грибами, а также содержащие их средства |
| JP2007523939A (ja) * | 2004-02-25 | 2007-08-23 | ビーエーエスエフ アクチェンゲゼルシャフト | アゾロピリミジン化合物及び寄生性菌類を駆除するためのその使用 |
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| CN1980932A (zh) * | 2004-06-22 | 2007-06-13 | 巴斯福股份公司 | 6－(2－甲苯基)三唑并嘧啶作为杀真菌剂的用途，新的6－(2－甲苯基) 三唑并嘧啶，其生产方法，其在防治有害真菌中的用途以及包含它们的试剂 |
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| EP1797095A1 (de) * | 2004-09-08 | 2007-06-20 | Basf Aktiengesellschaft | 6-phenyl-7-amino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| EP1853608B1 (de) * | 2005-02-16 | 2008-07-09 | Basf Se | 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| WO2007099092A1 (de) * | 2006-02-28 | 2007-09-07 | Basf Se | Substituierte 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a]pyrimidine und deren verwendung zur bekämpfung von schadpilzen |
| RU2325390C1 (ru) * | 2007-01-29 | 2008-05-27 | Государственное образовательное учреждение высшего профессионального образования "Южно-Российский государственный технический университет (Новочеркасский политехнический институт)" | СПОСОБ ПОЛУЧЕНИЯ 2-СУЛЬФОНИЛАМИНО-1,2,4,-ТРИАЗОЛО[1,5-a] ПИРИМИДИНОВ |
| EP1952690A3 (en) | 2007-01-31 | 2009-04-22 | Basf Se | Pesticidal mixtures based on triazolopyrimidines and insecticides |
| EP1952691A3 (en) | 2007-01-31 | 2008-09-17 | Basf Se | Method for improving plant health by application of a triazolopyrimidine derivative |
| RU2461197C1 (ru) * | 2011-05-03 | 2012-09-20 | Михаил Аркадьевич Ершов | Стимулятор для предпосевной обработки семян зерновых культур |
| RU2460298C1 (ru) * | 2011-05-03 | 2012-09-10 | Михаил Аркадьевич Ершов | Стимулятор для предпосевной обработки семян зерновых культур |
| RU2460297C1 (ru) * | 2011-05-04 | 2012-09-10 | Михаил Аркадьевич Ершов | Способ стимуляции всхожести семян |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1567021A (enExample) * | 1967-01-27 | 1969-05-16 | ||
| DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| HU208693B (en) * | 1991-02-22 | 1993-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
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1992
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- 1992-12-23 NZ NZ245581A patent/NZ245581A/en not_active IP Right Cessation
- 1992-12-24 AU AU30435/92A patent/AU667204B2/en not_active Ceased
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- 1992-12-28 DK DK97105710T patent/DK0782997T3/da active
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- 1992-12-28 HU HU9204135A patent/HU217349B/hu not_active IP Right Cessation
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- 1992-12-28 PL PL92312883A patent/PL171579B1/pl not_active IP Right Cessation
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1996
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