JP3438892B2 - 殺菌剤としてのジハロトリアゾロピリミジン誘導体 - Google Patents
殺菌剤としてのジハロトリアゾロピリミジン誘導体Info
- Publication number
- JP3438892B2 JP3438892B2 JP51957694A JP51957694A JP3438892B2 JP 3438892 B2 JP3438892 B2 JP 3438892B2 JP 51957694 A JP51957694 A JP 51957694A JP 51957694 A JP51957694 A JP 51957694A JP 3438892 B2 JP3438892 B2 JP 3438892B2
- Authority
- JP
- Japan
- Prior art keywords
- hal
- chlorine atom
- represent
- atom
- chlorine
- 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
- 239000000417 fungicide Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 239000000460 chlorine Substances 0.000 claims abstract description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- -1 phenoxy, naphthoxy Chemical group 0.000 claims description 76
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 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 14
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001544 thienyl group Chemical group 0.000 claims description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 2
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
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- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
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- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GVOUFPWUYJWQSK-UHFFFAOYSA-N Cyclofenil Chemical group C1=CC(OC(=O)C)=CC=C1C(C=1C=CC(OC(C)=O)=CC=1)=C1CCCCC1 GVOUFPWUYJWQSK-UHFFFAOYSA-N 0.000 claims 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
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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 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93103464 | 1993-03-04 | ||
| EP93103464.9 | 1993-03-04 | ||
| PCT/EP1994/000635 WO1994020501A1 (en) | 1993-03-04 | 1994-03-03 | Dihalotriazolopyrimidine derivatives as fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08507505A JPH08507505A (ja) | 1996-08-13 |
| JP3438892B2 true JP3438892B2 (ja) | 2003-08-18 |
Family
ID=8212658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51957694A Expired - Fee Related JP3438892B2 (ja) | 1993-03-04 | 1994-03-03 | 殺菌剤としてのジハロトリアゾロピリミジン誘導体 |
Country Status (25)
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 |
| US5756815A (en) * | 1997-03-18 | 1998-05-26 | American Cyanamid Company | Process for the preparation arylamalonates |
| US5750766A (en) * | 1997-03-18 | 1998-05-12 | American Cyanamid Company | Process for the preparation of arylmalonates |
| US6117876A (en) | 1997-04-14 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| 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 |
| US6284762B1 (en) * | 1998-03-23 | 2001-09-04 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6242451B1 (en) * | 1998-09-25 | 2001-06-05 | Klaus-Juergen Pees | Fungicidal trihalophenyl-triazolopyrimidines |
| 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 |
| US6156925A (en) * | 1998-09-25 | 2000-12-05 | American Cyanamid Company | Process for the preparation of halogenated phenylmaloates |
| US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| NZ523807A (en) * | 2000-06-30 | 2004-09-24 | Wyeth Corp | Substituted-triazolopyrimidines as anticancer agents |
| 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 |
| EP1616870A1 (de) | 2001-07-05 | 2006-01-18 | Basf Aktiengesellschaft | Fungizide Triazolopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen sowie sie enthaltende Mittel |
| BR0211180A (pt) * | 2001-07-18 | 2004-08-10 | Basf Ag | Compostos, processo para preparar os mesmos, intermediários, e, composição adequada e método para controlar fungos fitopatogênicos |
| ATE357142T1 (de) | 2001-07-26 | 2007-04-15 | Basf Ag | 7-aminotriazolopyrimidine zur bekämpfung von schadpilzen |
| 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 |
| US20060167017A1 (en) * | 2002-12-17 | 2006-07-27 | Basf Aktiengesellschaft | Fungicidal triazolopyrimidines, method for the production thereof, use thereof for controlling harmful fungl, and agents containing said fungicadal triazolopyrimidines |
| DE10325133A1 (de) * | 2003-06-04 | 2004-12-23 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10328173A1 (de) * | 2003-06-24 | 2005-01-13 | Bayer Cropscience Ag | Triazolopyrimidine |
| BRPI0414778A (pt) | 2003-09-24 | 2006-11-21 | Wyeth Corp | 6-aril-7-halo-imidazo[1,2-a]pirimidinas como agentes anticáncer |
| SI1680425T1 (sl) * | 2003-09-24 | 2007-04-30 | Wyeth Corp | 6-((substituirani)fenil)triazolopirimidini kot sredstva proti raku |
| 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 |
| DE10360370A1 (de) * | 2003-12-22 | 2005-07-14 | Bayer Cropscience Ag | Triazolopyrimidine |
| WO2005087773A1 (de) * | 2004-03-10 | 2005-09-22 | Basf Aktiengesellschaft | 5,6-dialkyl-7-amino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| US20070185099A1 (en) * | 2004-06-25 | 2007-08-09 | Carsten Blettner | 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 |
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| US2553500A (en) * | 1946-08-01 | 1951-05-15 | Gen Aniline & Film Corp | Production of photographs in blue-black tones and compositions thereof |
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| US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
| TW224044B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| 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 |
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1994
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- 1994-03-03 SK SK1068-95A patent/SK106895A3/sk unknown
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- 1994-03-03 RU RU95121948A patent/RU2130459C1/ru not_active IP Right Cessation
- 1994-03-03 CZ CZ952233A patent/CZ284158B6/cs not_active IP Right Cessation
- 1994-03-03 UA UA95083957A patent/UA61871C2/uk unknown
- 1994-03-03 DK DK94909922T patent/DK0699200T3/da active
- 1994-03-03 CN CN94191368A patent/CN1041927C/zh not_active Expired - Fee Related
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- 1994-03-03 AU AU62580/94A patent/AU690899B2/en not_active Ceased
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