Fluoxastrobin

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Structural formula
Structural formula of fluoxastrobin
Structural formula of the ( E ) isomer
General
Surname Fluoxastrobin
other names
  • ( E ) - (2- [6- (2-Chlorophenoxy) -5-fluoropyrimidin-4-yloxy] phenyl) (5,6-dihydro-1,4,2-dioxazin-3-yl) methanone- O- methyloxime ( IUPAC )
  • (1 E ) - (2 - [(6- (2-Chlorophenoxy) -5-fluoro-4-pyrimidinyl) oxy] phenyl) (5,6-dihydro-1,4,2-dioxazin-3-yl) methanone - O -methyloxime
Molecular formula C 21 H 16 ClFN 4 O 5
Brief description

white solid

External identifiers / databases
CAS number 361377-29-9
EC number 609-207-6
ECHA InfoCard 100.127.748
PubChem 11048796
Wikidata Q15632878
properties
Molar mass 458.83 g mol −1
Physical state

firmly

Melting point

103-105 ° C

Vapor pressure

6 10 −10 Pa (20 ° C)

solubility
  • practically insoluble in water (2.29 mg l −1 at 20 ° C)
  • soluble in acetone, acetonitrile and dichloromethane
safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 317-400
P: 273-280
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fluoxastrobin is a chemical compound from the group of strobilurins and methoxyacrylates , which is used as a fungicide in agriculture.

Extraction and presentation

Fluoxastrobin can be obtained by a multi-stage reaction of 2-bromo-2'-hydroxyacetophenone with H 2 NOMe, potassium tert -butanolate , tert-butyl nitrite , ethylene oxide , potassium hydroxide , 4,5,6-trifluoropyrimidine and 2-chlorophenol .

properties

Fluoxastrobin is a white solid that is practically insoluble in water. It is stable to hydrolysis . Although the ( E ) isomer is generally referred to as fluoxastrobin, the ( Z ) isomer is also contained in a minor amount in the technical product . The isomer ratio ( E ): ( Z ) is at least 90:10.

use

Fluoxastrobin is used as a fungicide in cereals and onions. In addition to the spray application, pickling agent applications are also used. The effect is based on the inhibition of complex III of the respiratory chain, the cytochrome c reductase , at the Qo point. It was launched by Bayer in 2004.

Admission

In the European Union, the active ingredient in plant protection fluoxastrobin was approved for use as a fungicide with effect from August 1, 2008.

In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products with this active ingredient are approved.

Individual evidence

  1. ↑ a b USEPA: Document Display Pesticides Fact Sheet for Fluoxastrobin 2005. Retrieved October 10, 2019 .
  2. ↑ a b c d e Fluoxastrobin data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
  3. ↑ a b c d BVL: Fluoxastrobin
  4. ↑ a b Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 592, 612 (English, limited preview in Google Book search).
  5. ↑ Bayer CropScience Deutschland GmbH: EfA®. Retrieved October 10, 2019 .
  6. ↑ Commission Directive 2008/44 / EC of April 4, 2008 amending Council Directive 91/414 / EEC to include the active substances benthiavalicarb, boscalid, carvone, fluoxastrobin, Paecilomyces lilacinus and prothioconazole
  7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on fluoxastrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.