CA2011087C - Use of trifluoromethylphenylazolylmethyloxiranes as crop protection agents - Google Patents
Use of trifluoromethylphenylazolylmethyloxiranes as crop protection agents Download PDFInfo
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- CA2011087C CA2011087C CA002011087A CA2011087A CA2011087C CA 2011087 C CA2011087 C CA 2011087C CA 002011087 A CA002011087 A CA 002011087A CA 2011087 A CA2011087 A CA 2011087A CA 2011087 C CA2011087 C CA 2011087C
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- phenyl
- hydrogen
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- HZSZWTQBLZPSPM-UHFFFAOYSA-N 2-[[2-phenyl-3-(trifluoromethyl)oxiran-2-yl]methyl]-1h-pyrrole Chemical class FC(F)(F)C1OC1(C=1C=CC=CC=1)CC1=CC=CN1 HZSZWTQBLZPSPM-UHFFFAOYSA-N 0.000 title abstract 2
- 239000011814 protection agent Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- -1 nitro, phenyl Chemical group 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 229910052751 metal Chemical class 0.000 claims abstract description 7
- 239000002184 metal Chemical class 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 241000233866 Fungi Species 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- ZFOWEXGOKLKOFQ-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-1h-pyrrole Chemical compound C=1C=CNC=1CC1CO1 ZFOWEXGOKLKOFQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 34
- 239000000417 fungicide Substances 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 239000004593 Epoxy Substances 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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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 3
- 150000002576 ketones Chemical class 0.000 description 3
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- 235000021012 strawberries Nutrition 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Mushroom Cultivation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3907729A DE3907729A1 (de) | 1989-03-10 | 1989-03-10 | Trifluormethylphenylazolylmethyloxirane, verfahren zu ihrer herstellung und deren verwendung als pflanzenschutzmittel |
| DEP3907729.2 | 1989-03-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2011087A1 CA2011087A1 (en) | 1990-09-10 |
| CA2011087C true CA2011087C (en) | 2000-12-12 |
Family
ID=6375971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002011087A Expired - Fee Related CA2011087C (en) | 1989-03-10 | 1990-02-26 | Use of trifluoromethylphenylazolylmethyloxiranes as crop protection agents |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0386557B1 (en, 2012) |
| JP (1) | JP2947287B2 (en, 2012) |
| KR (1) | KR900014370A (en, 2012) |
| AT (1) | ATE77086T1 (en, 2012) |
| AU (1) | AU621721B2 (en, 2012) |
| CA (1) | CA2011087C (en, 2012) |
| DE (2) | DE3907729A1 (en, 2012) |
| DK (1) | DK0386557T3 (en, 2012) |
| ES (1) | ES2036852T3 (en, 2012) |
| GR (1) | GR3005671T3 (en, 2012) |
| HU (1) | HU206434B (en, 2012) |
| IL (1) | IL93443A (en, 2012) |
| NZ (1) | NZ232844A (en, 2012) |
| ZA (1) | ZA901834B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9095136B2 (en) | 2011-11-25 | 2015-08-04 | Bayer Intellectual Property Gmbh | 2-IODO imidazole-derivatives |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3805684A1 (de) * | 1988-02-24 | 1989-09-07 | Basf Ag | Azolylmethylcycloalkyloxirane, ihre herstellung und verwendung als pflanzenschutzmittel |
| DE4028392A1 (de) * | 1990-09-07 | 1992-03-12 | Basf Ag | Azolylmethyloxirane und diese enthaltende fungizide |
| US20080245434A1 (en) | 2005-03-28 | 2008-10-09 | Motoshige Hibino | Composite Hose with a Corrugated Metal Tube and Method for Making the Same |
| KR20090031580A (ko) * | 2006-06-21 | 2009-03-26 | 바스프 에스이 | 아졸릴메틸옥시란, 식물병원성 진균을 방제하기 위한 그 용도, 및 이를 포함하는 조성물 |
| BRPI0713678A2 (pt) * | 2006-06-23 | 2012-10-23 | Basf Se | compostos, uso de compostos, composição para a proteção de cultura, semente, e, processo para combater fungos fitopatogênicos |
| WO2007147769A1 (de) * | 2006-06-23 | 2007-12-27 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
| EP2041122B1 (de) * | 2006-07-05 | 2009-11-25 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
| US20090197929A1 (en) * | 2006-07-05 | 2009-08-06 | Basf Se | Azolylmethyloxiranes, Their Use for Controlling Phytopathogenic Fungi and Agents Containing Said Compounds |
| JP5148610B2 (ja) * | 2006-07-24 | 2013-02-20 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン、植物病原菌類を防除するためのその使用、およびそれを含む薬剤 |
| JP2009544650A (ja) * | 2006-07-25 | 2009-12-17 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン、植物病原菌類を防除するためのその使用、およびそれを含む薬剤 |
| CN101568259A (zh) | 2006-12-22 | 2009-10-28 | 巴斯夫欧洲公司 | 唑基甲基环氧乙烷、其在防治植物病原性真菌中的用途以及包含它们的组合物 |
| BRPI0821362A2 (pt) * | 2007-12-19 | 2014-10-14 | Basf Se | Composto, uso do mesmo, composição, semente, método para controlar fungos fitopatogênicos, medicamento, e, processos para preparar um antimicótico e para preparar compostos |
| EP2235005A2 (de) * | 2007-12-19 | 2010-10-06 | Basf Se | Azolylmethyloxirane, ihre verwendung sowie sie enthaltende mittel |
| BRPI0821296A2 (pt) * | 2007-12-19 | 2014-10-07 | Basf Se | Composto, uso de um composto, composição, semente, método para controlar fungos fitopatogênicos, medicamento, e, processos para preparar um antimicótico e compostos |
| WO2011069912A1 (de) | 2009-12-07 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2011069894A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2011069916A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung als fungizide sowie sie enthaltende mittel |
| BR112012023157B1 (pt) | 2010-03-16 | 2018-08-07 | Basf Se | Processos para preparar um composto, compostos, uso de um composto e uso de um reagente de grignard |
| CN103228650A (zh) | 2010-09-30 | 2013-07-31 | 巴斯夫欧洲公司 | 合成含有硫代三唑并基团的化合物的方法 |
| WO2012130823A1 (en) | 2011-03-30 | 2012-10-04 | Basf Se | Suspension concentrates |
| EP2746277A1 (en) * | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
| CN109996796A (zh) | 2016-09-29 | 2019-07-09 | 拜耳作物科学股份公司 | 作为杀真菌剂的5-取代的咪唑基甲基环氧乙烷衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3218130A1 (de) * | 1982-05-14 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| DE3218129A1 (de) * | 1982-05-14 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Azolylmethyloxirane, ihre herstellung und verwendung als arzneimittel |
| DE3511411A1 (de) * | 1985-03-29 | 1986-10-02 | Basf Ag, 6700 Ludwigshafen | Verwendung von azolylmethyloxiranen zur bekaempfung von viralen erkrankungen |
| DE3737888A1 (de) * | 1987-11-07 | 1989-05-18 | Basf Ag | Verfahren zur beeinflussung des pflanzenwachstums durch azolylmethyloxirane |
| DE3807951A1 (de) * | 1988-03-10 | 1989-09-21 | Basf Ag | Fungizide imidazolylmethyloxirane |
-
1989
- 1989-03-10 DE DE3907729A patent/DE3907729A1/de not_active Withdrawn
-
1990
- 1990-02-19 IL IL9344390A patent/IL93443A/en not_active IP Right Cessation
- 1990-02-24 EP EP90103616A patent/EP0386557B1/de not_active Expired - Lifetime
- 1990-02-24 DE DE9090103616T patent/DE59000151D1/de not_active Expired - Lifetime
- 1990-02-24 ES ES199090103616T patent/ES2036852T3/es not_active Expired - Lifetime
- 1990-02-24 AT AT90103616T patent/ATE77086T1/de not_active IP Right Cessation
- 1990-02-24 DK DK90103616.0T patent/DK0386557T3/da active
- 1990-02-26 CA CA002011087A patent/CA2011087C/en not_active Expired - Fee Related
- 1990-03-08 NZ NZ23284490A patent/NZ232844A/en unknown
- 1990-03-09 AU AU51178/90A patent/AU621721B2/en not_active Ceased
- 1990-03-09 HU HU901383A patent/HU206434B/hu not_active IP Right Cessation
- 1990-03-09 JP JP2056792A patent/JP2947287B2/ja not_active Expired - Fee Related
- 1990-03-09 ZA ZA901834A patent/ZA901834B/xx unknown
- 1990-03-10 KR KR1019900003280A patent/KR900014370A/ko not_active Ceased
-
1992
- 1992-09-10 GR GR920401997T patent/GR3005671T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9095136B2 (en) | 2011-11-25 | 2015-08-04 | Bayer Intellectual Property Gmbh | 2-IODO imidazole-derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ232844A (en) | 1994-07-26 |
| DK0386557T3 (da) | 1992-07-27 |
| AU5117890A (en) | 1990-09-13 |
| JPH02268182A (ja) | 1990-11-01 |
| HU901383D0 (en) | 1990-05-28 |
| GR3005671T3 (en, 2012) | 1993-06-07 |
| DE3907729A1 (de) | 1990-09-13 |
| EP0386557B1 (de) | 1992-06-10 |
| AU621721B2 (en) | 1992-03-19 |
| DE59000151D1 (de) | 1992-07-16 |
| ES2036852T3 (es) | 1993-06-01 |
| HUT53782A (en) | 1990-12-28 |
| JP2947287B2 (ja) | 1999-09-13 |
| HU206434B (en) | 1992-11-30 |
| ZA901834B (en) | 1991-11-27 |
| KR900014370A (ko) | 1990-10-23 |
| ATE77086T1 (de) | 1992-06-15 |
| IL93443A (en) | 1994-05-30 |
| CA2011087A1 (en) | 1990-09-10 |
| EP0386557A1 (de) | 1990-09-12 |
| IL93443A0 (en) | 1990-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |