AU667204B2 - Triazolopyrimidine derivatives - Google Patents
Triazolopyrimidine derivatives Download PDFInfo
- Publication number
- AU667204B2 AU667204B2 AU30435/92A AU3043592A AU667204B2 AU 667204 B2 AU667204 B2 AU 667204B2 AU 30435/92 A AU30435/92 A AU 30435/92A AU 3043592 A AU3043592 A AU 3043592A AU 667204 B2 AU667204 B2 AU 667204B2
- Authority
- AU
- Australia
- Prior art keywords
- group
- compound
- formula
- phenyl
- alkyl
- 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.)
- Ceased
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- 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 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 110
- -1 026 Chemical group 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 230000000855 fungicidal effect Effects 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 229910052740 iodine Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 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
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 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
- 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 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
- 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
- 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
- 238000011160 research Methods 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
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 58
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
- 241000196324 Embryophyta Species 0.000 description 48
- 230000000694 effects Effects 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000007921 spray Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000000338 in vitro Methods 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
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- 239000004094 surface-active agent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 240000003768 Solanum lycopersicum Species 0.000 description 9
- 241000209140 Triticum Species 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 239000007900 aqueous suspension Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 235000021186 dishes Nutrition 0.000 description 8
- 239000001965 potato dextrose agar Substances 0.000 description 8
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
- 238000011081 inoculation Methods 0.000 description 7
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- 239000000725 suspension Substances 0.000 description 7
- 241000213004 Alternaria solani Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 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
- 230000002538 fungal effect Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 241000123650 Botrytis cinerea Species 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- 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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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- YTWWZMWSDHIENY-UHFFFAOYSA-N n-cyclopentyl-5-fluoro-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1F YTWWZMWSDHIENY-UHFFFAOYSA-N 0.000 description 1
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- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
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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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP91122422 | 1991-12-30 | ||
| EP91122422 | 1991-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3043592A AU3043592A (en) | 1993-07-01 |
| AU667204B2 true AU667204B2 (en) | 1996-03-14 |
Family
ID=8207489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU30435/92A Ceased AU667204B2 (en) | 1991-12-30 | 1992-12-24 | Triazolopyrimidine derivatives |
Country Status (21)
| Country | Link |
|---|---|
| EP (2) | EP0782997B1 (enExample) |
| JP (1) | JP3347170B2 (enExample) |
| KR (1) | KR100271913B1 (enExample) |
| CN (2) | CN1033643C (enExample) |
| AT (2) | ATE192154T1 (enExample) |
| AU (1) | AU667204B2 (enExample) |
| BR (1) | BR9205172A (enExample) |
| CA (1) | CA2086404C (enExample) |
| DE (2) | DE69230977T2 (enExample) |
| DK (2) | DK0782997T3 (enExample) |
| ES (2) | ES2147411T3 (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) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
| IL108731A (en) * | 1993-03-04 | 1997-03-18 | Shell Int Research | 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES |
| IL108747A (en) * | 1993-03-04 | 1999-03-12 | Shell Int Research | Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| RU2147584C1 (ru) * | 1995-10-27 | 2000-04-20 | Американ Цианамид Компани | Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов |
| US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
| US5750766A (en) * | 1997-03-18 | 1998-05-12 | American Cyanamid Company | Process for the preparation of arylmalonates |
| US5756815A (en) * | 1997-03-18 | 1998-05-26 | American Cyanamid Company | Process for the preparation arylamalonates |
| TW460476B (en) * | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6117876A (en) * | 1997-04-14 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| CN1114606C (zh) * | 1998-02-11 | 2003-07-16 | 美国氰胺公司 | 具有杀真菌活性的7－烷基－三唑并嘧啶化合物 |
| JPH11322517A (ja) * | 1998-03-17 | 1999-11-24 | American Cyanamid Co | トリアゾロピリミジン類の効力の増進 |
| US6124301A (en) * | 1998-03-17 | 2000-09-26 | American Cyanamid Company | Enhancement of the efficacy of triazolopyrimidines |
| US6284762B1 (en) * | 1998-03-23 | 2001-09-04 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| PE20001145A1 (es) * | 1998-09-10 | 2000-10-25 | American Cyanamid Co | Mezclas fungicidas |
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| RU2461197C1 (ru) * | 2011-05-03 | 2012-09-20 | Михаил Аркадьевич Ершов | Стимулятор для предпосевной обработки семян зерновых культур |
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| DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
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1992
- 1992-12-17 TW TW081110143A patent/TW224044B/zh active
- 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
- 1992-12-28 JP JP35863292A patent/JP3347170B2/ja not_active Expired - Fee Related
- 1992-12-28 AT AT97105710T patent/ATE192154T1/de not_active IP Right Cessation
- 1992-12-28 ZA ZA9210043A patent/ZA9210043B/xx unknown
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- 1992-12-28 DE DE69230977T patent/DE69230977T2/de not_active Expired - Fee Related
- 1992-12-28 EP EP97105710A patent/EP0782997B1/en not_active Expired - Lifetime
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- 1992-12-28 CN CN92115232.9A patent/CN1033643C/zh not_active Expired - Fee Related
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- 1992-12-28 DE DE69222746T patent/DE69222746T2/de not_active Expired - Fee Related
- 1992-12-28 SG SG1996002843A patent/SG47563A1/en unknown
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- 1992-12-28 HU HU9204135A patent/HU217349B/hu not_active IP Right Cessation
- 1992-12-28 PT PT97105710T patent/PT782997E/pt unknown
- 1992-12-28 EP EP92204097A patent/EP0550113B1/en not_active Expired - Lifetime
- 1992-12-28 ES ES92204097T patent/ES2108727T3/es not_active Expired - Lifetime
- 1992-12-28 IL IL104244A patent/IL104244A/xx not_active IP Right Cessation
- 1992-12-28 RU RU9292016218A patent/RU2089552C1/ru not_active IP Right Cessation
- 1992-12-28 DK DK92204097.7T patent/DK0550113T3/da active
- 1992-12-28 PL PL92312883A patent/PL171579B1/pl not_active IP Right Cessation
- 1992-12-29 CA CA002086404A patent/CA2086404C/en not_active Expired - Fee Related
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1996
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1998
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2000
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| FR1567021A (enExample) * | 1967-01-27 | 1969-05-16 | ||
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