PL174047B1 - Sposób wytwarzania pochodnych triazolopirymidyny - Google Patents
Sposób wytwarzania pochodnych triazolopirymidynyInfo
- Publication number
- PL174047B1 PL174047B1 PL92297160A PL29716092A PL174047B1 PL 174047 B1 PL174047 B1 PL 174047B1 PL 92297160 A PL92297160 A PL 92297160A PL 29716092 A PL29716092 A PL 29716092A PL 174047 B1 PL174047 B1 PL 174047B1
- Authority
- PL
- Poland
- Prior art keywords
- compound
- phenyl
- formula
- group
- cycloalkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000000855 fungicidal effect Effects 0.000 title description 18
- 239000000417 fungicide Substances 0.000 title description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 3
- 150000003852 triazoles Chemical class 0.000 title 2
- 239000000460 chlorine Substances 0.000 claims abstract description 91
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- 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 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 azepan-i-yl Chemical group 0.000 claims description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 3
- RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 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 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 2
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
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- 241000196324 Embryophyta Species 0.000 description 45
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
- 239000000203 mixture Substances 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
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- 239000002904 solvent Substances 0.000 description 16
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 238000005507 spraying Methods 0.000 description 13
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- 230000009471 action Effects 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 238000000338 in vitro Methods 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 11
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000007900 aqueous suspension Substances 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
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- 241000233866 Fungi Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 240000003768 Solanum lycopersicum Species 0.000 description 9
- 241000209140 Triticum Species 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 8
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- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
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- 230000001681 protective effect Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 4
- 241000213004 Alternaria solani Species 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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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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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- 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 description 1
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- 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
- 239000003350 kerosene Substances 0.000 description 1
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 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
- 239000000025 natural resin Substances 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000012807 shake-flask culturing Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
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- 239000000057 synthetic resin Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP91122422 | 1991-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL297160A1 PL297160A1 (en) | 1993-09-06 |
| PL174047B1 true PL174047B1 (pl) | 1998-06-30 |
Family
ID=8207489
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92297160A PL174047B1 (pl) | 1991-12-30 | 1992-12-28 | Sposób wytwarzania pochodnych triazolopirymidyny |
| PL92312883A PL171579B1 (pl) | 1991-12-30 | 1992-12-28 | Srodek grzybobójczy PL |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92312883A PL171579B1 (pl) | 1991-12-30 | 1992-12-28 | Srodek grzybobójczy PL |
Country Status (21)
| Country | Link |
|---|---|
| EP (2) | EP0550113B1 (show.php) |
| JP (1) | JP3347170B2 (show.php) |
| KR (1) | KR100271913B1 (show.php) |
| CN (2) | CN1033643C (show.php) |
| AT (2) | ATE192154T1 (show.php) |
| AU (1) | AU667204B2 (show.php) |
| BR (1) | BR9205172A (show.php) |
| CA (1) | CA2086404C (show.php) |
| DE (2) | DE69230977T2 (show.php) |
| DK (2) | DK0550113T3 (show.php) |
| ES (2) | ES2108727T3 (show.php) |
| GR (2) | GR3025920T3 (show.php) |
| HU (1) | HU217349B (show.php) |
| IL (1) | IL104244A (show.php) |
| NZ (1) | NZ245581A (show.php) |
| PL (2) | PL174047B1 (show.php) |
| PT (1) | PT782997E (show.php) |
| RU (1) | RU2089552C1 (show.php) |
| SG (1) | SG47563A1 (show.php) |
| TW (1) | TW224044B (show.php) |
| ZA (1) | ZA9210043B (show.php) |
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 |
| 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 |
| 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 |
| 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 |
| PT1054888E (pt) * | 1998-02-11 | 2004-02-27 | Basf Ag | 7-alquil-triazolopirimidinas fungicidas |
| US6124301A (en) * | 1998-03-17 | 2000-09-26 | American Cyanamid Company | Enhancement of the efficacy of triazolopyrimidines |
| 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 |
| 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 |
| US6242451B1 (en) * | 1998-09-25 | 2001-06-05 | Klaus-Juergen Pees | Fungicidal trihalophenyl-triazolopyrimidines |
| US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6277856B1 (en) | 1998-09-25 | 2001-08-21 | American Cynamid Co. | Fungicidal mixtures |
| JP2000103790A (ja) * | 1998-09-25 | 2000-04-11 | American Cyanamid Co | 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類 |
| 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 |
| KR100638150B1 (ko) * | 1998-12-23 | 2006-10-26 | 이데아 악티엔게젤샤프트 | 생체내에서 국부적인 비침습성 용도로 사용되는 개선된 제제 |
| US6699874B2 (en) | 1999-09-24 | 2004-03-02 | Basf Aktiengesellschaft | Fungicidal mixtures |
| GB2355261A (en) * | 1999-10-13 | 2001-04-18 | American Cyanamid Co | Triazolopyrimidine fungicides |
| US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| AU2001278445A1 (en) * | 2000-06-13 | 2001-12-24 | Basf Aktiengesellschaft | Fungicidal triazolopyrimid-7-ylideneamines |
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| JP2004515502A (ja) * | 2000-12-06 | 2004-05-27 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺真菌性を有する６−（トリフルオロメチル−フェニル）−トリアゾロピリミジン類 |
| DE10063115A1 (de) * | 2000-12-18 | 2002-06-27 | Bayer Ag | Triazolopyrimidine |
| ATE270292T1 (de) * | 2001-04-09 | 2004-07-15 | Basf Ag | Fungizide 5-alkylamino-6-phenyl-7-halogen- triazolopyrimidine |
| US7071334B2 (en) | 2001-04-11 | 2006-07-04 | Basf Aktiengesellschaft | 6-(2-chloro-6-fluoro-phenyl)-triazolopyrimidines |
| EP1381609B1 (en) | 2001-04-11 | 2005-01-19 | Basf Aktiengesellschaft | 5-halogen-6-phenyl-7-fluoroalkylamino-triazolopyrimidines as fungicides |
| DE10121101A1 (de) | 2001-04-27 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10121162A1 (de) * | 2001-04-30 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
| EP1634863A1 (de) | 2001-07-05 | 2006-03-15 | Basf Aktiengesellschaft | Zwischenprodukte zur Herstellung von fungiziden Triazolopyrimidinen |
| WO2003008416A1 (en) * | 2001-07-18 | 2003-01-30 | Basf Aktiengesellschaft | Substituted 6-(2-methoxyphenyl) triazolopyrimides as fungicides |
| IL159605A0 (en) * | 2001-07-18 | 2004-06-01 | Basf Ag | 6-(2,6-difluorophenyl)-triazolopyrimidines as fungicides |
| JP2005504744A (ja) * | 2001-07-18 | 2005-02-17 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌薬としての置換された６−（２−トリル）−トリアゾロピリミジン |
| ATE357142T1 (de) | 2001-07-26 | 2007-04-15 | Basf Ag | 7-aminotriazolopyrimidine zur bekämpfung von schadpilzen |
| DE60220296T2 (de) | 2001-09-04 | 2008-01-17 | Sumitomo Chemical Co., Ltd. | IMIDAZO(1,2-a)PYRIMIDINE UND DIESE ENTHALTENDE FUNGIZIDZUSAMMENSETZUNGEN |
| GB0126914D0 (en) * | 2001-11-08 | 2002-01-02 | Syngenta Ltd | Fungicides |
| CN1324030C (zh) | 2002-03-21 | 2007-07-04 | 巴斯福股份公司 | 杀真菌的三唑并嘧啶、其制备方法、其在防治有害真菌中的用途和包含所述物质的试剂 |
| DE10212886A1 (de) * | 2002-03-22 | 2003-10-02 | Bayer Cropscience Ag | Triazolopyrimidine |
| UA80304C2 (en) * | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
| PL376886A1 (pl) * | 2002-11-15 | 2006-01-09 | Basf Aktiengesellschaft | 2-Merkapto-podstawione triazolopirymidyny, sposoby ich wytwarzania, ich zastosowanie do zwalczania szkodliwych grzybów i zawierające je środki |
| WO2004055018A1 (de) * | 2002-12-17 | 2004-07-01 | Basf Aktiengesellschaft | Fungizide triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| JP2007523843A (ja) * | 2003-03-31 | 2007-08-23 | ビーエーエスエフ アクチェンゲゼルシャフト | ７−アルケニルアミノ−トリアゾロピリミジン、その製造方法、有害菌類を防除するためのその使用及びそれらを含む製剤 |
| EA008920B1 (ru) * | 2003-04-02 | 2007-08-31 | Басф Акциенгезельшафт | 7-алкиниламинотриазолопиримидины, способ их получения и их применение для борьбы с патогенными грибами, а также содержащие их средства |
| CL2004000817A1 (es) * | 2003-04-17 | 2005-04-15 | Basf Ag | Compuestos biciclos que contienen n; composicion que las contiene; utiles para combatir hongos fitopatogenos. |
| UY28506A1 (es) * | 2003-09-12 | 2005-04-29 | Basf Ag | 6-halógeno-(1,2,4)triazolo(1,5-a)pirimidinas para combatir plagas animales. |
| PL1680425T3 (pl) | 2003-09-24 | 2007-05-31 | Wyeth Corp | 6-[(podstawione)fenylo]triazolopirymidyny jako środki przeciwrakowe |
| BRPI0414778A (pt) | 2003-09-24 | 2006-11-21 | Wyeth Corp | 6-aril-7-halo-imidazo[1,2-a]pirimidinas como agentes anticáncer |
| 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 |
| MY179926A (en) | 2003-12-08 | 2020-11-19 | Wyeth Corp | Process for the preparation of tubulin inhibitors |
| EP1697367A1 (de) * | 2003-12-18 | 2006-09-06 | Basf Aktiengesellschaft | 6-(2-halogenphenyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowie sie enthaltende mittel |
| EP1720879A2 (de) * | 2004-02-25 | 2006-11-15 | Basf Aktiengesellschaft | Azolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| EP1751162A1 (de) * | 2004-05-17 | 2007-02-14 | Basf Aktiengesellschaft | Triazolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| US20070249634A1 (en) * | 2004-06-09 | 2007-10-25 | Carsten Blettner | Triazolopyrimidine Compounds and Use Thereof for Controlling Harmful Fungi |
| MXPA06014145A (es) * | 2004-06-22 | 2007-03-07 | Basf Ag | Uso de 6-(2-tolil)-triazolopirimidinas como fungicidas, nuevas 6-(2-tolil)-triazolopirimidinas, procedimientos para su preparacion y el uso de las mismas para combatir hongos nocivos, asi como productos que las contienen. |
| WO2005123739A1 (de) * | 2004-06-22 | 2005-12-29 | Basf Aktiengesellschaft | 6-(2-fluorphenyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| AR049944A1 (es) * | 2004-06-25 | 2006-09-20 | Basf Ag | Compuestos de triazolopirimidina y su uso en el control de hongos daninos |
| BRPI0513032A (pt) * | 2004-07-08 | 2008-04-22 | Basf Ag | compostos, processo para preparar os mesmos, agente fungicida, semente, e, processo para combater fungos nocivos fitopatogênicos |
| AP2007003927A0 (en) * | 2004-09-08 | 2007-02-28 | Basf Ag | 6-Phenyl-7 aminotriazolopyrimidines, processes fortheir preparation and their use for controlling h armful fungi, and also compositions comprising them |
| DE502006001074D1 (de) * | 2005-02-16 | 2008-08-21 | Basf Se | 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| AR059649A1 (es) * | 2006-02-28 | 2008-04-16 | Basf Ag | 6- fenil 7-amino - amino (1,2,4) -triazolo (1,5-a) pirimidinas y su su uso para el combate de hongos daninos |
| 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 |
| EP1952691A3 (en) | 2007-01-31 | 2008-09-17 | Basf Se | Method for improving plant health by application of a triazolopyrimidine derivative |
| EP1952690A3 (en) | 2007-01-31 | 2009-04-22 | Basf Se | Pesticidal mixtures based on triazolopyrimidines and insecticides |
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1567021A (show.php) * | 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
- 1992-12-17 TW TW081110143A patent/TW224044B/zh active
- 1992-12-23 NZ NZ245581A patent/NZ245581A/en not_active IP Right Cessation
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- 1992-12-28 DK DK92204097.7T patent/DK0550113T3/da active
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- 1992-12-28 RU RU9292016218A patent/RU2089552C1/ru not_active IP Right Cessation
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- 1992-12-28 PL PL92297160A patent/PL174047B1/pl not_active IP Right Cessation
- 1992-12-28 PL PL92312883A patent/PL171579B1/pl not_active IP Right Cessation
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1996
- 1996-03-22 CN CN96103723A patent/CN1074650C/zh not_active Expired - Fee Related
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2000
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| LAPS | Decisions on the lapse of the protection rights |
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