DE69406538T2 - Dihalotriazolopyrimidinderivate als fugizide - Google Patents
Dihalotriazolopyrimidinderivate als fugizideInfo
- Publication number
- DE69406538T2 DE69406538T2 DE69406538T DE69406538T DE69406538T2 DE 69406538 T2 DE69406538 T2 DE 69406538T2 DE 69406538 T DE69406538 T DE 69406538T DE 69406538 T DE69406538 T DE 69406538T DE 69406538 T2 DE69406538 T2 DE 69406538T2
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- necks
- halves
- compound
- bromine
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 71
- 239000000460 chlorine Substances 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 37
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000417 fungicide Substances 0.000 claims abstract description 7
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- -1 phenoxy, naphthoxy Chemical group 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 230000002538 fungal effect Effects 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-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)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93103464 | 1993-03-04 | ||
| PCT/EP1994/000635 WO1994020501A1 (en) | 1993-03-04 | 1994-03-03 | Dihalotriazolopyrimidine derivatives as fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69406538D1 DE69406538D1 (de) | 1997-12-04 |
| DE69406538T2 true DE69406538T2 (de) | 1998-02-26 |
Family
ID=8212658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69406538T Expired - Fee Related DE69406538T2 (de) | 1993-03-04 | 1994-03-03 | Dihalotriazolopyrimidinderivate als fugizide |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5854252A (enExample) |
| EP (1) | EP0699200B1 (enExample) |
| JP (1) | JP3438892B2 (enExample) |
| KR (1) | KR100313052B1 (enExample) |
| CN (1) | CN1041927C (enExample) |
| AT (1) | ATE159722T1 (enExample) |
| AU (1) | AU690899B2 (enExample) |
| BR (1) | BR9405988A (enExample) |
| CA (1) | CA2157293A1 (enExample) |
| CZ (1) | CZ284158B6 (enExample) |
| DE (1) | DE69406538T2 (enExample) |
| DK (1) | DK0699200T3 (enExample) |
| GE (1) | GEP19981488B (enExample) |
| HU (1) | HU219977B (enExample) |
| IL (1) | IL108747A (enExample) |
| MD (1) | MD968C2 (enExample) |
| NZ (1) | NZ262729A (enExample) |
| PL (1) | PL179164B1 (enExample) |
| RU (1) | RU2130459C1 (enExample) |
| SG (1) | SG48860A1 (enExample) |
| SK (1) | SK106895A3 (enExample) |
| TW (1) | TW283624B (enExample) |
| UA (1) | UA61871C2 (enExample) |
| WO (1) | WO1994020501A1 (enExample) |
| ZA (1) | ZA941485B (enExample) |
Families Citing this family (39)
| 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 |
| 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 |
| US6117876A (en) * | 1997-04-14 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| TW460476B (en) * | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| TWI252231B (en) * | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
| US6284762B1 (en) * | 1998-03-23 | 2001-09-04 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| 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 |
| US6156925A (en) * | 1998-09-25 | 2000-12-05 | American Cyanamid Company | Process for the preparation of halogenated phenylmaloates |
| 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 |
| US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| JP2004502691A (ja) * | 2000-06-30 | 2004-01-29 | ワイス | 抗癌薬としての置換トリアゾロピリミジン |
| DE10063115A1 (de) * | 2000-12-18 | 2002-06-27 | Bayer Ag | Triazolopyrimidine |
| JP2002249492A (ja) * | 2000-12-22 | 2002-09-06 | Nippon Bayer Agrochem Co Ltd | トリアゾロピリミジン類 |
| DE60104087T2 (de) * | 2001-04-09 | 2004-10-28 | Basf Ag | Fungizide 5-Alkylamino-6-phenyl-7-halogen-Triazolopyrimidine |
| DE10121101A1 (de) * | 2001-04-27 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10121162A1 (de) * | 2001-04-30 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| KR100619216B1 (ko) | 2001-07-05 | 2006-09-08 | 바스프 악티엔게젤샤프트 | 살진균성 트리아졸로피리미딘, 이의 제조방법 및 유해진균 방제를 위한 이의 용도 및 상기 화합물을 포함하는조성물 |
| CN1271071C (zh) * | 2001-07-18 | 2006-08-23 | 巴斯福股份公司 | 作为杀真菌剂的取代的6－(2－甲苯基)－三唑并嘧啶 |
| ES2283626T3 (es) * | 2001-07-26 | 2007-11-01 | Basf Aktiengesellschaft | 7-aminotriazolpirimidinas para controlar hongos nocivos. |
| GB0126914D0 (en) * | 2001-11-08 | 2002-01-02 | Syngenta Ltd | Fungicides |
| DE10212886A1 (de) * | 2002-03-22 | 2003-10-02 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10218592A1 (de) * | 2002-04-26 | 2003-11-06 | Bayer Cropscience Ag | Triazolopyrimidine |
| CN1738822A (zh) * | 2002-12-17 | 2006-02-22 | 巴斯福股份公司 | 杀真菌的三唑并嘧啶、其生产方法及其防治有害真菌的用途以及包含所述杀真菌的三唑并嘧啶的试剂 |
| DE10325133A1 (de) * | 2003-06-04 | 2004-12-23 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10328173A1 (de) * | 2003-06-24 | 2005-01-13 | Bayer Cropscience Ag | Triazolopyrimidine |
| 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 |
| BRPI0414700A (pt) | 2003-09-24 | 2006-11-14 | Wyeth Corp | 6-[(substituìdo)fenil]triazolopirimidinas como agentes anti-cáncer |
| CA2537520A1 (en) * | 2003-09-24 | 2005-04-07 | Wyeth Holdings Corporation | 6-aryl-7-halo-imidazo[1,2-a]pyrimidines as anticancer agents |
| MY179926A (en) | 2003-12-08 | 2020-11-19 | Wyeth Corp | Process for the preparation of tubulin inhibitors |
| DE10360370A1 (de) * | 2003-12-22 | 2005-07-14 | Bayer Cropscience Ag | Triazolopyrimidine |
| PL1725561T3 (pl) * | 2004-03-10 | 2010-12-31 | Basf Se | 5,6-Dialkilo-7-aminotriazolopirymidyny, sposób ich wytwarzania i ich zastosowanie do zwalczania szkodliwych grzybów oraz środki zawierające te związki |
| CA2570578A1 (en) * | 2004-06-25 | 2006-01-05 | Basf Aktiengesellschaft | Triazolopyrimidine compounds and their use for controlling pathogenic fungi |
| RU2340614C2 (ru) * | 2006-05-24 | 2008-12-10 | Государственное Образовательное Учреждение Высшего Профессионального Образования Уральский Государственный Технический Университет-УПИ | 2-r-4-(аллилоксиметил)-6-нитро-1,2,4-триазоло[5,1-с]-1,2,4-триазин-7(4н)-оны и 2-r-4-(пропаргилоксиметил)-6-нитро-1,2,4-триазоло[5,1-с]-1,2,4-триазин7(4н)-оны, обладающие противовирусным действием |
| RU2345080C2 (ru) * | 2007-02-16 | 2009-01-27 | ГОУ ВПО Уральский государственный технический университет-УПИ | 4-(4'-ГИДРОКСИБУТИЛ)-6-ФЕНИЛ-1,2,4-ТРИАЗОЛО[5,1-c][1,2,4]ТРИАЗИН-7-ОН |
| RU2427128C2 (ru) * | 2009-12-14 | 2011-08-27 | Государственное научное учреждение Всероссийский научно-исследовательский институт риса Российской академии сельскохозяйственных наук (ГНУ ВНИИ риса) | Способ оценки устойчивости исходного селекционного материала риса к пирикуляриозу |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553500A (en) * | 1946-08-01 | 1951-05-15 | Gen Aniline & Film Corp | Production of photographs in blue-black tones and compositions thereof |
| GB1235834A (en) * | 1969-02-28 | 1971-06-16 | Ici Ltd | Pharmaceutical compositions |
| FR2223371A1 (en) * | 1973-03-29 | 1974-10-25 | Ici Ltd | Thiazolo (3,2-a) pyrimidines - as plant antibacterials |
| US4572910A (en) * | 1983-03-03 | 1986-02-25 | Riker Laboratories, Inc. | Triazolo[1,5-c]pyrimidines substituted by nitrogen-containing heterocyclic rings |
| FR2549834B1 (fr) * | 1983-07-25 | 1985-10-18 | Sanofi Sa | Derives de triazolo-pyrimidine, leur procede de preparation et leur application therapeutique en tant que tonicardiaques |
| DE3338292A1 (de) * | 1983-10-21 | 1985-05-02 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)-pyrimidine und diese enthaltende fungizide |
| DE3533050A1 (de) * | 1985-09-17 | 1987-03-26 | Basf Ag | 7-amino-azolo(1,5-a)pyrimidine, verfahren zu ihrer herstellung und diese enthaltende fungizide, bzw. deren verwendung als fungizide |
| GB8610532D0 (en) * | 1986-04-30 | 1986-06-04 | Fbc Ltd | Herbicides |
| GB8610531D0 (en) * | 1986-04-30 | 1986-06-04 | Fbc Ltd | Herbicides |
| DE3640155A1 (de) * | 1986-11-25 | 1988-05-26 | Bayer Ag | Triazolo-pyrimidin-2-sulfonamide |
| DE3644343A1 (de) * | 1986-12-19 | 1988-06-30 | Schering Ag | 6,7-dihydro-(1,2,4)triazolo(1,5-a)(1,3,5) triazin-2-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider und wachstumsregulierender wirkung |
| JP2999808B2 (ja) * | 1990-08-20 | 2000-01-17 | 第一製薬株式会社 | ２位置換トリアゾロピリミジン類 |
| TW224044B (enExample) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| 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 |
-
1994
- 1994-02-23 IL IL10874794A patent/IL108747A/en not_active IP Right Cessation
- 1994-03-01 TW TW083101746A patent/TW283624B/zh active
- 1994-03-03 SG SG1996003137A patent/SG48860A1/en unknown
- 1994-03-03 KR KR1019950703812A patent/KR100313052B1/ko not_active Expired - Fee Related
- 1994-03-03 NZ NZ262729A patent/NZ262729A/en not_active IP Right Cessation
- 1994-03-03 DK DK94909922T patent/DK0699200T3/da active
- 1994-03-03 RU RU95121948A patent/RU2130459C1/ru not_active IP Right Cessation
- 1994-03-03 AU AU62580/94A patent/AU690899B2/en not_active Ceased
- 1994-03-03 JP JP51957694A patent/JP3438892B2/ja not_active Expired - Fee Related
- 1994-03-03 CZ CZ952233A patent/CZ284158B6/cs not_active IP Right Cessation
- 1994-03-03 US US08/424,535 patent/US5854252A/en not_active Expired - Lifetime
- 1994-03-03 MD MD96-0297A patent/MD968C2/ro unknown
- 1994-03-03 CA CA002157293A patent/CA2157293A1/en not_active Abandoned
- 1994-03-03 GE GEAP19942859A patent/GEP19981488B/en unknown
- 1994-03-03 HU HU9501926A patent/HU219977B/hu not_active IP Right Cessation
- 1994-03-03 DE DE69406538T patent/DE69406538T2/de not_active Expired - Fee Related
- 1994-03-03 EP EP94909922A patent/EP0699200B1/en not_active Expired - Lifetime
- 1994-03-03 CN CN94191368A patent/CN1041927C/zh not_active Expired - Fee Related
- 1994-03-03 SK SK1068-95A patent/SK106895A3/sk unknown
- 1994-03-03 BR BR9405988A patent/BR9405988A/pt not_active IP Right Cessation
- 1994-03-03 UA UA95083957A patent/UA61871C2/uk unknown
- 1994-03-03 WO PCT/EP1994/000635 patent/WO1994020501A1/en not_active Ceased
- 1994-03-03 AT AT94909922T patent/ATE159722T1/de not_active IP Right Cessation
- 1994-03-03 ZA ZA941485A patent/ZA941485B/xx unknown
- 1994-03-03 PL PL94310467A patent/PL179164B1/pl not_active IP Right Cessation
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1995
- 1995-06-05 US US08/464,349 patent/US5612345A/en not_active Expired - Fee Related
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