CA1171866A - Phenyl triazole ethanols and their use as fungicides - Google Patents
Phenyl triazole ethanols and their use as fungicidesInfo
- Publication number
- CA1171866A CA1171866A CA000364347A CA364347A CA1171866A CA 1171866 A CA1171866 A CA 1171866A CA 000364347 A CA000364347 A CA 000364347A CA 364347 A CA364347 A CA 364347A CA 1171866 A CA1171866 A CA 1171866A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- alpha
- ethanol
- triazole
- compound
- 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
Links
- 239000000417 fungicide Substances 0.000 title description 9
- -1 Phenyl triazole ethanols Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 241000233866 Fungi Species 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 150000004696 coordination complex Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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- 238000007254 oxidation reaction Methods 0.000 claims description 3
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
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- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
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- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- LWXGIHBXXQBLEU-UHFFFAOYSA-N bis(2-tert-butyl-4-methylphenyl)methanone Chemical compound C(C)(C)(C)C1=C(C=CC(=C1)C)C(=O)C1=C(C=C(C=C1)C)C(C)(C)C LWXGIHBXXQBLEU-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001586 eradicative effect Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical group [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- MCOWGUNDBBHKAM-UHFFFAOYSA-N thiohypoiodous acid Chemical compound IS MCOWGUNDBBHKAM-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9379979A | 1979-11-13 | 1979-11-13 | |
| US93,799 | 1979-11-13 | ||
| US16861380A | 1980-07-14 | 1980-07-14 | |
| US168,613 | 1980-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171866A true CA1171866A (en) | 1984-07-31 |
Family
ID=26787917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000364347A Expired CA1171866A (en) | 1979-11-13 | 1980-11-10 | Phenyl triazole ethanols and their use as fungicides |
Country Status (25)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9253983B2 (en) | 2011-05-31 | 2016-02-09 | Kureha Corporation | Triazole compound and use thereof |
| US10053436B2 (en) | 2014-07-08 | 2018-08-21 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
| US10344008B2 (en) | 2015-05-08 | 2019-07-09 | BASF Agro B.V. | Process for the preparation of terpinolene epoxide |
| US10538470B2 (en) | 2015-05-08 | 2020-01-21 | BASF Agro B.V. | Process for the preparation of limonene-4-ol |
| US10640477B2 (en) | 2016-06-15 | 2020-05-05 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| US11072593B2 (en) | 2016-06-15 | 2021-07-27 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4927839A (en) * | 1979-03-07 | 1990-05-22 | Imperial Chemical Industries Plc | Method of preventing fungal attack on wood, hides, leather or paint films using a triazole |
| ATE81852T1 (de) * | 1980-08-18 | 1992-11-15 | Ici Plc | Triazol-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als fungizide und pflanzenwachstumsregulatoren. |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
| US4533659A (en) * | 1982-06-09 | 1985-08-06 | Ciba-Geigy Corporation | Microbicidal 2-(1H-1,2,4-triazolylmethyl-1'-yl)-2-siloxy-2-phenyl-acetates |
| US4517194A (en) * | 1982-06-25 | 1985-05-14 | Ciba-Geigy Corporation | Azolylmandelic acid derivatives and use thereof for controlling microorganisms |
| DE3337937A1 (de) * | 1982-10-28 | 1984-05-03 | Sandoz-Patent-GmbH, 7850 Lörrach | Neue azolderivate |
| DE3381852D1 (de) * | 1982-11-10 | 1990-10-04 | Ici Plc | Verfahren zur herstellung von verbindungen mit doppelter kohlenstoff-kohlenstoffbindung durch dehydrierung des korrespondierenden alkohols. |
| PH19709A (en) * | 1982-11-23 | 1986-06-16 | Ciba Geigy Ag | Microbicidal 1-carbonyl-1-phenoxyphenyl-2-azolylethanol derivatives |
| AT395363B (de) * | 1983-03-04 | 1992-12-10 | Sandoz Ag | Verfahren zur bekaempfung phytopathogener fungi |
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
| ATE66676T1 (de) * | 1983-05-19 | 1991-09-15 | Ciba Geigy Ag | Verfahren zur herstellung von 1triazolylethylether-derivaten, sowie mikrobizide mittel enthaltende neue 1-triazolyl- phenoxyphenylethylether-derivate als wirkstoffe und deren verwendung. |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
| CH668772A5 (de) * | 1984-07-13 | 1989-01-31 | Sandoz Ag | 1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. |
| GB8603951D0 (en) * | 1986-02-18 | 1986-03-26 | Ici Plc | Heterocyclic compounds |
| GB8617780D0 (en) * | 1986-07-21 | 1986-08-28 | Sandoz Ltd | Fungicides |
| FR2609368B1 (fr) * | 1987-01-14 | 1990-04-13 | Sandoz Sa Produits | Utilisation de derives du 1, 2, 4-triazole pour combattre les maladies de plaies de taille des plantes perennes |
| DE3800094C2 (de) * | 1987-01-14 | 1998-05-14 | Ciba Geigy Ag | Verfahren und hydrophobe Zubereitung zur Bekämpfung von Schnittwundparasiten bei Pflanzen |
| ES2016660B3 (es) * | 1987-01-21 | 1990-11-16 | Ciba-Geigy Ag | Agente microbicida. |
| BE1001499A5 (fr) * | 1988-07-14 | 1989-11-14 | Sandoz Sa | Procede pour combattre les maladies de plaies de taille des plantes perennes. |
| DE3909862A1 (de) * | 1989-03-25 | 1990-09-27 | Basf Ag | Azolylethylcyclopropane, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel |
| GB9307924D0 (en) * | 1993-04-16 | 1993-06-02 | Zeneca Ltd | Chrial synthesis |
| HU212424B (en) * | 1993-09-23 | 1996-06-28 | Richter Gedeon Vegyeszet | New propan-2-ol derivatives substituted with triazole or imidazole and process for producing them |
| EP1606999A1 (de) * | 2004-06-18 | 2005-12-21 | Bayer CropScience AG | Saatgutbehandlungsmittel für Soja |
| WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
| WO2014082871A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| EP2928873A1 (en) | 2012-11-27 | 2015-10-14 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| EP2935237A1 (en) | 2012-12-19 | 2015-10-28 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
| EP3173406A1 (en) | 2012-12-19 | 2017-05-31 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
| CN105050406B (zh) * | 2012-12-20 | 2017-09-15 | 巴斯夫农业公司 | 包含三唑化合物的组合物 |
| EP3219707B1 (en) | 2013-01-09 | 2019-06-26 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
| EP3019013B1 (en) * | 2013-07-08 | 2020-12-23 | BASF Agro B.V. | Compositions comprising a triazole compound and a biopesticide |
| MX377786B (es) | 2013-12-18 | 2025-03-10 | Basf Agro Bv | Procedimiento para la preparacion de cetonas fenoxifenilicas sustituidas. |
| AR100743A1 (es) * | 2014-06-06 | 2016-10-26 | Basf Se | Compuestos de [1,2,4]triazol sustituido |
| EP2952507A1 (en) * | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
| UA119672C2 (uk) | 2014-06-25 | 2019-07-25 | Басф Агро Б.В. | Пестицидні композиції |
| PL3214937T3 (pl) | 2014-11-07 | 2024-10-14 | Basf Se | Mieszaniny szkodnikobójcze |
| CN104814029B (zh) * | 2015-03-12 | 2017-10-17 | 南京林业大学 | 水载型复合有机木材防腐剂及其制备方法和应用 |
| BR112018068695B1 (pt) | 2016-03-16 | 2022-12-27 | Basf Se | Uso de um composto e método para controlar fungos fitopatogênicos |
| WO2017157916A1 (en) | 2016-03-16 | 2017-09-21 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean |
| CA3015744C (en) | 2016-03-16 | 2024-04-23 | Basf Se | Use of 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one for combating resistant phytopathogenic fungi on cereals |
| CN110740995B (zh) * | 2017-06-14 | 2023-07-14 | 巴斯夫农业公司 | 制备取代苯氧基苯基醇的方法 |
| CN107602547A (zh) * | 2017-09-28 | 2018-01-19 | 南开大学 | 一类杂环三唑衍生物及其制备方法和用途 |
| EP3670487A1 (en) | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of substituted phenoxyphenyl ketones |
| EP3670491A1 (en) | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-trifluoromethyl-acetophenone |
| EP3670492A1 (en) | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-(trifluoromethyl)-1-(1-nitroethyl)-benzene |
| EP3696165A1 (en) | 2019-02-14 | 2020-08-19 | BASF Agro B.V. | Process for the preparation of 4-halophenoxy-2-trifluoromethyl benzonitrile |
| EP3696164A1 (en) | 2019-02-14 | 2020-08-19 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-(trifluoromethyl)-benzonitrile |
| EP3696159A1 (en) | 2019-02-14 | 2020-08-19 | BASF Agro B.V. | Process for the preparation of substituted phenoxyphenyl ketones |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| IE44186B1 (en) * | 1975-12-03 | 1981-09-09 | Ici Ltd | 1,2,4-triazolyl alkanols and their use as pesticides |
| IE45765B1 (en) * | 1976-08-19 | 1982-11-17 | Ici Ltd | Triazoles and imidazoles useful as plant fungicides and growth regulating agents |
| DE2738725A1 (de) * | 1977-08-27 | 1979-03-08 | Basf Ag | Azolylalkohole |
| DE2743767A1 (de) * | 1977-09-29 | 1979-04-12 | Bayer Ag | Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1980
- 1980-11-06 CH CH8251/80A patent/CH647513A5/de not_active IP Right Cessation
- 1980-11-08 DE DE19803042302 patent/DE3042302A1/de active Granted
- 1980-11-10 IT IT50119/80A patent/IT1184252B/it active
- 1980-11-10 CA CA000364347A patent/CA1171866A/en not_active Expired
- 1980-11-10 GB GB8036066A patent/GB2064520B/en not_active Expired
- 1980-11-11 PT PT72047A patent/PT72047B/pt unknown
- 1980-11-11 EG EG80704A patent/EG14737A/xx active
- 1980-11-11 ES ES496714A patent/ES496714A0/es active Granted
- 1980-11-11 AU AU64263/80A patent/AU545756B2/en not_active Expired
- 1980-11-11 IL IL61453A patent/IL61453A/xx not_active IP Right Cessation
- 1980-11-11 AT AT0553580A patent/AT378368B/de not_active IP Right Cessation
- 1980-11-11 HU HU802702A patent/HU185917B/hu unknown
- 1980-11-11 GR GR63332A patent/GR71877B/el unknown
- 1980-11-12 FR FR8024029A patent/FR2469408A1/fr active Granted
- 1980-11-12 DK DK483680A patent/DK158041C/da not_active IP Right Cessation
- 1980-11-12 IE IE2353/80A patent/IE51003B1/en not_active IP Right Cessation
- 1980-11-12 NL NLAANVRAGE8006170,A patent/NL185207C/xx not_active IP Right Cessation
- 1980-11-12 PL PL1980227788A patent/PL126776B1/pl unknown
- 1980-11-12 CS CS807663A patent/CS235510B2/cs unknown
- 1980-11-12 BR BR8007385A patent/BR8007385A/pt unknown
- 1980-11-12 DZ DZ806017A patent/DZ253A1/fr active
- 1980-11-12 YU YU02891/80A patent/YU289180A/xx unknown
-
1981
- 1981-03-27 PH PH25440A patent/PH17803A/en unknown
-
1986
- 1986-10-14 KE KE3668A patent/KE3668A/xx unknown
- 1986-12-30 MY MY442/86A patent/MY8600442A/xx unknown
-
1987
- 1987-12-30 MY MY561/87A patent/MY8700561A/xx unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9253983B2 (en) | 2011-05-31 | 2016-02-09 | Kureha Corporation | Triazole compound and use thereof |
| US10053436B2 (en) | 2014-07-08 | 2018-08-21 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
| US10344008B2 (en) | 2015-05-08 | 2019-07-09 | BASF Agro B.V. | Process for the preparation of terpinolene epoxide |
| US10538470B2 (en) | 2015-05-08 | 2020-01-21 | BASF Agro B.V. | Process for the preparation of limonene-4-ol |
| US10640477B2 (en) | 2016-06-15 | 2020-05-05 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| US11072593B2 (en) | 2016-06-15 | 2021-07-27 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
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