Oxathiapiproline
| Structural formula | |||||||||||||||||||
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| Simplified structural formula without stereochemistry 1: 1 mixture of the ( R ) - and the ( S ) -form |
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| General | |||||||||||||||||||
| Surname | Oxathiapiproline | ||||||||||||||||||
| other names |
rac -1- (4- {4 - [(5 R ) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2) -yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1 H -pyrazol-1-yl] ethan-1-one |
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| Molecular formula | C 24 H 22 F 5 N 5 O 2 S | ||||||||||||||||||
| Brief description |
almost white, crystalline solid |
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| properties | |||||||||||||||||||
| Molar mass | 539.52 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
146.4 ° C |
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| boiling point |
disintegrates before boiling at 289.5 ° C |
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| Vapor pressure |
1.141 hPa (20 ° C) |
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| solubility |
practically insoluble in water (0.1749 mg l −1 at 20 ° C) |
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| safety instructions | |||||||||||||||||||
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| Toxicological data | |||||||||||||||||||
| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Oxathiapiproline is a chemical compound from the group of oxazoles , pyrazoles and thiazoles .
history
The DuPont company acquired a substance library from an external dealer, with which some tests were initially carried out. A structure with a slightly fungicidal effect was discovered in the first screenings. By examining the structure-activity relationships, the effect could be further optimized through the introduction of various side groups, so that in the end oxathiapiproline was developed as the best active ingredient. This has a fungicidal effect 10,000 times greater than the starting material. In 2013, the active ingredient was licensed by Syngenta and brought onto the market.
presentation
Dichloroacetone is nitrosated to dichloroketoxime , which reacts further through a (3 + 2) cycloaddition with styrene to form the isoxazoline derivative. The reaction with BOC -protected piperidine thioamide produces a thiazole . After the BOC group has been deprotected, it reacts with (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetic acid to form oxathiapiptroline.
properties
Oxathiapiproline is an almost colorless, crystalline solid. It is practically insoluble in water and very stable to hydrolysis . In the soil it is persistent with a half-life of approx. 121 days. The molecule has a stereocenter . Two different isomers are therefore possible. The fungicide oxathiapiproline is used as a racemate . The pure enantiomers are of no practical importance.
Use and mode of action
Oxathiapiproline is a fungicide of the piperidinylthiazolisoxazoline class. It has a systemic effect and can be used both preventively and curatively against downy mildew and attack by Phytophthora , whereby it also inhibits the formation of spores in the target organisms. It is used in viticulture, potato cultivation and the cultivation of vegetables, lettuce and herbs. The effect of Oxathiapiproline is based on the strong binding to the Oxysterol-Binding Protein 1 of Oomycetes , the exact mechanism being unknown.
toxicology
In animal experiments, oxathiapiproline is only slightly acutely toxic after oral, dermal and inhalation ingestion. In addition, it is neither irritating nor sensitizing to the skin or eyes. In addition, it was found that only a small amount of active substance is absorbed after oral intake (approx. 30%). Neither genotoxic nor carcinogenic potential could be observed. The European Food Safety Authority set a permitted daily dose of 0.14 mg / kg body weight.
Admission
Oxathiapiproline was approved for ten years in the European Union on March 3, 2017. While in Switzerland no pesticides with Oxathiapiprolin are available in Germany and Austria drugs approved with this drug.
Individual evidence
- ↑ a b c d e f g h i j Entry on oxathiapiproline in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on October 10, 2019.
- ↑ a b Safety Data Sheet - Oxathiapiproline. (PDF) In: HPC Standards GmbH. May 16, 2019, accessed October 10, 2019 .
- ↑ a b Peter Jeschke, Matthias Witschel, Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2019, ISBN 978-3-527-34089-7 ( limited preview in Google Book Search [accessed August 5, 2019]).
- ^ A b Scriven, Eric FV, Ramsden, Christopher A., 1946-: Heterocyclic chemistry in the 21st Century: a tribute to Alan Katritzky . [Place of publication not identified], ISBN 978-0-12-812070-5 ( limited preview in Google book search).
- ^ Richard Schaffer, Filiberto Agusti, Lucien Dhooge: International Business Law and Its Environment . Cengage Learning, 2014, ISBN 1-305-14301-9 , pp. 463 ( limited preview in Google Book search).
- ↑ syngenta.com: Syngenta and DuPont agree on a technology exchange to introduce new fungicide solutions ( Memento from September 24, 2015 in the Internet Archive ), accessed on April 15, 2020.
- ↑ Jiang, Xuefeng,: Sulfur chemistry . Cham, ISBN 978-3-03025598-5 ( limited preview in Google book search).
- ↑ Peer review of the pesticide risk assessment of the active substance oxathiapiprolin . In: EFSA Journal . tape 14 , no. 7 , 2016, ISSN 1831-4732 , p. e04504 , doi : 10.2903 / j.efsa.2016.4504 .
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on Oxathiapiproline in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on April 14, 2020.