CA2443696A1 - 5-halogen-6-phenyl-7-fluoroalkylamino-triazolopyrimidines as fungicides - Google Patents
5-halogen-6-phenyl-7-fluoroalkylamino-triazolopyrimidines as fungicides Download PDFInfo
- Publication number
- CA2443696A1 CA2443696A1 CA002443696A CA2443696A CA2443696A1 CA 2443696 A1 CA2443696 A1 CA 2443696A1 CA 002443696 A CA002443696 A CA 002443696A CA 2443696 A CA2443696 A CA 2443696A CA 2443696 A1 CA2443696 A1 CA 2443696A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- hydrogen
- compounds
- alkyl
- halogen
- 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.)
- Abandoned
Links
- 239000000417 fungicide Substances 0.000 title description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 18
- 241000233866 Fungi Species 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 73
- -1 nitro, hydroxyl Chemical group 0.000 claims description 38
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 230000002538 fungal effect Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004991 fluoroalkenyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
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- 241000196324 Embryophyta Species 0.000 description 31
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000855 fungicidal effect Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- 244000070406 Malus silvestris Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 229910052725 zinc Inorganic materials 0.000 description 4
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
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- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 2
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- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- OYRIKLVYHTWHCZ-UHFFFAOYSA-N n-cyclohexyl-2,5-dimethylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2CCCCC2)=C1C OYRIKLVYHTWHCZ-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- QXJKBPAVAHBARF-UHFFFAOYSA-N procymidone Chemical compound O=C1C2(C)CC2(C)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01109011.5 | 2001-04-11 | ||
| EP01109011 | 2001-04-11 | ||
| PCT/EP2002/003829 WO2002083676A1 (en) | 2001-04-11 | 2002-04-06 | 5-halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2443696A1 true CA2443696A1 (en) | 2002-10-24 |
Family
ID=8177112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002443696A Abandoned CA2443696A1 (en) | 2001-04-11 | 2002-04-06 | 5-halogen-6-phenyl-7-fluoroalkylamino-triazolopyrimidines as fungicides |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7105664B2 (https=) |
| EP (1) | EP1381609B1 (https=) |
| JP (1) | JP2004531527A (https=) |
| KR (1) | KR20030087073A (https=) |
| CN (1) | CN1257904C (https=) |
| AR (1) | AR035823A1 (https=) |
| AT (1) | ATE287405T1 (https=) |
| AU (1) | AU2002257757B2 (https=) |
| BG (1) | BG108238A (https=) |
| BR (1) | BR0208756A (https=) |
| CA (1) | CA2443696A1 (https=) |
| CZ (1) | CZ295558B6 (https=) |
| DE (1) | DE60202672T2 (https=) |
| EA (1) | EA006710B1 (https=) |
| EE (1) | EE200300499A (https=) |
| ES (1) | ES2236509T3 (https=) |
| HU (1) | HUP0401092A3 (https=) |
| IL (1) | IL158218A0 (https=) |
| MX (1) | MXPA03009002A (https=) |
| NZ (1) | NZ528745A (https=) |
| PL (1) | PL367107A1 (https=) |
| PT (1) | PT1381609E (https=) |
| SK (1) | SK12522003A3 (https=) |
| TW (1) | TWI275590B (https=) |
| UA (1) | UA74069C2 (https=) |
| WO (1) | WO2002083676A1 (https=) |
| ZA (1) | ZA200307888B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255309B1 (en) * | 1999-03-19 | 2001-07-03 | American Cyanomid Co. | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
| UA80304C2 (en) * | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
| CA2504192A1 (en) * | 2002-11-07 | 2004-05-21 | Basf Aktiengesellschaft | 5-alkyl-7-aminotriazolopyrimidines, methods and intermediary products necessary for the production thereof, agents containing said compounds and the use thereof for fighting against harmful mushrooms |
| OA12957A (en) * | 2002-11-15 | 2006-10-13 | Basf Ag | Fungicidal mixtures. |
| GB0230020D0 (en) * | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230018D0 (en) * | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| EP1611135A1 (de) * | 2003-03-31 | 2006-01-04 | Basf Aktiengesellschaft | 7-alkenylamino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowie sie enthaltende mittel |
| CN100355754C (zh) * | 2003-04-02 | 2007-12-19 | 巴斯福股份公司 | 7－炔基氨基三唑并嘧啶、其制备方法及其在防治有害真菌中的用途以及包含所述化合物的制剂 |
| ES2279452T3 (es) | 2003-09-24 | 2007-08-16 | Wyeth Holdings Corporation | 6-((sustituido)fenil)triazolopirimidinas como agentes antineoplasicos. |
| CN100486580C (zh) | 2003-09-24 | 2009-05-13 | 惠氏控股公司 | 作为抗癌剂的6-芳基-7-卤基-咪唑并[1,2-a]嘧啶 |
| US7419982B2 (en) | 2003-09-24 | 2008-09-02 | Wyeth Holdings Corporation | Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts |
| JP2008501754A (ja) * | 2004-06-09 | 2008-01-24 | ビーエーエスエフ アクチェンゲゼルシャフト | トリアゾロピリミジン化合物および有害菌類を防除するためのその使用 |
| BRPI0512249A (pt) * | 2004-06-22 | 2008-02-19 | Basf Ag | compostos, processos para a preparação dos mesmos, e para o combate de fungos nocivos fitopatogênicos, agente fungicida, e, semente |
| EP1920654A1 (en) | 2006-09-13 | 2008-05-14 | Syngeta Participations AG | Novel pyridopyrazine N-oxides |
| EP1952691A3 (en) * | 2007-01-31 | 2008-09-17 | Basf Se | Method for improving plant health by application of a triazolopyrimidine derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3130633A1 (de) | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| TW224044B (https=) | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| TWI252231B (en) | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
| TW460476B (en) * | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| GEP20053688B (en) * | 2000-06-30 | 2005-12-12 | Wyeth Corp | Substituted-Triazolopyrimidines as Anticancer Agents |
-
2002
- 2002-04-06 PL PL02367107A patent/PL367107A1/xx not_active Application Discontinuation
- 2002-04-06 EP EP02727533A patent/EP1381609B1/en not_active Expired - Lifetime
- 2002-04-06 MX MXPA03009002A patent/MXPA03009002A/es active IP Right Grant
- 2002-04-06 KR KR10-2003-7013281A patent/KR20030087073A/ko not_active Abandoned
- 2002-04-06 HU HU0401092A patent/HUP0401092A3/hu unknown
- 2002-04-06 EA EA200301105A patent/EA006710B1/ru not_active IP Right Cessation
- 2002-04-06 CZ CZ20032721A patent/CZ295558B6/cs not_active IP Right Cessation
- 2002-04-06 IL IL15821802A patent/IL158218A0/xx unknown
- 2002-04-06 AT AT02727533T patent/ATE287405T1/de not_active IP Right Cessation
- 2002-04-06 JP JP2002581431A patent/JP2004531527A/ja not_active Withdrawn
- 2002-04-06 NZ NZ528745A patent/NZ528745A/en unknown
- 2002-04-06 PT PT02727533T patent/PT1381609E/pt unknown
- 2002-04-06 DE DE60202672T patent/DE60202672T2/de not_active Expired - Fee Related
- 2002-04-06 SK SK1252-2003A patent/SK12522003A3/sk unknown
- 2002-04-06 CA CA002443696A patent/CA2443696A1/en not_active Abandoned
- 2002-04-06 CN CNB028080807A patent/CN1257904C/zh not_active Expired - Fee Related
- 2002-04-06 WO PCT/EP2002/003829 patent/WO2002083676A1/en not_active Ceased
- 2002-04-06 AU AU2002257757A patent/AU2002257757B2/en not_active Ceased
- 2002-04-06 BR BR0208756-1A patent/BR0208756A/pt not_active IP Right Cessation
- 2002-04-06 ES ES02727533T patent/ES2236509T3/es not_active Expired - Lifetime
- 2002-04-06 EE EEP200300499A patent/EE200300499A/xx unknown
- 2002-04-06 US US10/474,460 patent/US7105664B2/en not_active Expired - Fee Related
- 2002-04-11 AR ARP020101339A patent/AR035823A1/es not_active Application Discontinuation
- 2002-04-11 TW TW091107358A patent/TWI275590B/zh not_active IP Right Cessation
- 2002-06-04 UA UA20031110122A patent/UA74069C2/uk unknown
-
2003
- 2003-10-07 BG BG108238A patent/BG108238A/bg unknown
- 2003-10-09 ZA ZA200307888A patent/ZA200307888B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR035823A1 (es) | 2004-07-14 |
| EA200301105A1 (ru) | 2004-02-26 |
| NZ528745A (en) | 2005-03-24 |
| US20040127509A1 (en) | 2004-07-01 |
| AU2002257757B2 (en) | 2008-05-08 |
| SK12522003A3 (sk) | 2004-05-04 |
| ATE287405T1 (de) | 2005-02-15 |
| WO2002083676A1 (en) | 2002-10-24 |
| US7105664B2 (en) | 2006-09-12 |
| JP2004531527A (ja) | 2004-10-14 |
| ES2236509T3 (es) | 2005-07-16 |
| TWI275590B (en) | 2007-03-11 |
| MXPA03009002A (es) | 2004-02-12 |
| BR0208756A (pt) | 2004-05-11 |
| CN1501936A (zh) | 2004-06-02 |
| EP1381609A1 (en) | 2004-01-21 |
| HUP0401092A3 (en) | 2005-10-28 |
| IL158218A0 (en) | 2004-05-12 |
| BG108238A (bg) | 2005-04-30 |
| CN1257904C (zh) | 2006-05-31 |
| EP1381609B1 (en) | 2005-01-19 |
| PT1381609E (pt) | 2005-05-31 |
| DE60202672T2 (de) | 2005-06-16 |
| PL367107A1 (en) | 2005-02-21 |
| CZ20032721A3 (cs) | 2004-01-14 |
| DE60202672D1 (de) | 2005-02-24 |
| KR20030087073A (ko) | 2003-11-12 |
| EA006710B1 (ru) | 2006-02-24 |
| CZ295558B6 (cs) | 2005-08-17 |
| ZA200307888B (en) | 2004-10-11 |
| EE200300499A (et) | 2003-12-15 |
| HUP0401092A2 (hu) | 2004-09-28 |
| UA74069C2 (en) | 2005-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |