DE60201089T2 - 6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine - Google Patents
6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine Download PDFInfo
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- DE60201089T2 DE60201089T2 DE60201089T DE60201089T DE60201089T2 DE 60201089 T2 DE60201089 T2 DE 60201089T2 DE 60201089 T DE60201089 T DE 60201089T DE 60201089 T DE60201089 T DE 60201089T DE 60201089 T2 DE60201089 T2 DE 60201089T2
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- -1 2-chloro-6-fluoro-phenyl Chemical group 0.000 title claims abstract description 113
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 239000011593 sulfur Substances 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 241000233866 Fungi Species 0.000 claims abstract description 7
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- GEGSUBXDJDLXDS-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)triazolo[4,5-d]pyrimidine Chemical class FC1=CC=CC(Cl)=C1N1C=C2N=NN=C2N=C1 GEGSUBXDJDLXDS-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
- 229910052736 halogen Inorganic materials 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
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
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- 239000002689 soil Substances 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
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- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 1
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- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
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- LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
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- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
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- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
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- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 1
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- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound 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
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 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 group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 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
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 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
- 125000003226 pyrazolyl group Chemical group 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 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
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
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- 238000003860 storage Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 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
- 125000001544 thienyl group Chemical group 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
- 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
- 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
-
- 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)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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 |
|---|---|---|---|
| EP01109010 | 2001-04-11 | ||
| EP01109010 | 2001-04-11 | ||
| PCT/EP2002/003830 WO2002083677A1 (en) | 2001-04-11 | 2002-04-06 | 6-(2-chloro-6-fluoro-phenyl)-triazolopyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60201089D1 DE60201089D1 (de) | 2004-09-30 |
| DE60201089T2 true DE60201089T2 (de) | 2004-12-30 |
Family
ID=8177111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60201089T Expired - Fee Related DE60201089T2 (de) | 2001-04-11 | 2002-04-06 | 6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7071334B2 (enExample) |
| EP (1) | EP1381610B1 (enExample) |
| JP (1) | JP2004526767A (enExample) |
| AT (1) | ATE274518T1 (enExample) |
| DE (1) | DE60201089T2 (enExample) |
| ES (1) | ES2225784T3 (enExample) |
| WO (1) | WO2002083677A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1412358A1 (en) * | 2001-07-18 | 2004-04-28 | Basf Aktiengesellschaft | 6-(2,6-difluorophenyl)-triazolopyrimidines as fungicides |
| ATE339421T1 (de) * | 2002-11-07 | 2006-10-15 | Basf Ag | 5-alkyl-7-aminotriazolopyrimidine,verfahren und zwischenprodukte zu ihrer herstellung ,sie enthaltende mittel sowie ihre verwendung zur bekämpfung von schadpilzen |
| MXPA05004369A (es) * | 2002-11-15 | 2005-07-05 | Basf Ag | Mezclas fungicidas. |
| GB0230018D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230020D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| CN1886404A (zh) * | 2003-11-25 | 2006-12-27 | 巴斯福股份公司 | 6-(2,4,6-三氟苯基)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组合物 |
| JP2007514678A (ja) * | 2003-12-17 | 2007-06-07 | ビーエーエスエフ アクチェンゲゼルシャフト | 6−(2,3,6−トリフルオロフェニル)トリアゾロピリミジン、その調製および有害真菌防除のためのその使用、ならびに当該化合物を含んでなる組成物 |
| PE20050594A1 (es) * | 2003-12-17 | 2005-10-18 | Basf Ag | 6-(2-fluoro-4-alcoxifenil)-triazolopirimidinas y procedimientos para su preparacion |
| ES2290777T3 (es) * | 2003-12-17 | 2008-02-16 | Basf Se | 6-(2-cloro-4-alcoxi-fenil)-triazolopirimidinas, procedimiento para su elaboracion y su empleo para la lucha contra los hongos nocivos, asi como agentes que los contengan. |
| EP1697364A1 (de) * | 2003-12-17 | 2006-09-06 | Basf Aktiengesellschaft | 6-pentafluorphenyl-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowi e sie enthaltende mittel |
| BRPI0417628A (pt) * | 2003-12-17 | 2007-03-27 | Basf Ag | composto, processo para preparar o mesmo, agente, semente, e, processo para combater fungos nocivos fitopatogênicos |
| CN1938313A (zh) * | 2004-03-30 | 2007-03-28 | 巴斯福股份公司 | 6-(2-氟苯基)三唑并嘧啶、其制备方法及其在防治病原性真菌中的用途以及包含它们的组合物 |
| EP1920654A1 (en) | 2006-09-13 | 2008-05-14 | Syngeta Participations AG | Novel pyridopyrazine N-oxides |
Family Cites Families (7)
| 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 (enExample) | 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 |
| US5994360A (en) * | 1997-07-14 | 1999-11-30 | American Cyanamid Company | Fungicidal 5-alkyl-triazolopyrimidines |
| IL137617A0 (en) * | 1998-02-11 | 2001-07-24 | American Cyanamid Co | Fungicidal 7-akyl-triazolopyrimidines |
| FR2784991B1 (fr) | 1998-09-25 | 2002-08-16 | American Cyanamid Co | 7-heterocyclyl-triazolopyrimidines fluoro-substituees et leur utilisation a titre de fongicides |
| CA2413802A1 (en) * | 2000-06-30 | 2002-01-10 | Mark R. Schmitt | Substituted-triazolopyrimidines as anticancer agents |
-
2002
- 2002-04-06 AT AT02727534T patent/ATE274518T1/de not_active IP Right Cessation
- 2002-04-06 JP JP2002581432A patent/JP2004526767A/ja not_active Withdrawn
- 2002-04-06 US US10/474,461 patent/US7071334B2/en not_active Expired - Fee Related
- 2002-04-06 ES ES02727534T patent/ES2225784T3/es not_active Expired - Lifetime
- 2002-04-06 WO PCT/EP2002/003830 patent/WO2002083677A1/en not_active Ceased
- 2002-04-06 EP EP02727534A patent/EP1381610B1/en not_active Expired - Lifetime
- 2002-04-06 DE DE60201089T patent/DE60201089T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60201089D1 (de) | 2004-09-30 |
| US20040110751A1 (en) | 2004-06-10 |
| ES2225784T3 (es) | 2005-03-16 |
| JP2004526767A (ja) | 2004-09-02 |
| US7071334B2 (en) | 2006-07-04 |
| EP1381610A1 (en) | 2004-01-21 |
| WO2002083677A1 (en) | 2002-10-24 |
| EP1381610B1 (en) | 2004-08-25 |
| ATE274518T1 (de) | 2004-09-15 |
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Owner name: BASF SE, 67063 LUDWIGSHAFEN, DE |
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| 8339 | Ceased/non-payment of the annual fee |