Flutriafol
Structural formula | |||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Simplified structural formula without stereochemistry | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Flutriafol | ||||||||||||||||||
other names |
|
||||||||||||||||||
Molecular formula | C 16 H 13 F 2 N 3 O | ||||||||||||||||||
Brief description |
colorless solid |
||||||||||||||||||
External identifiers / databases | |||||||||||||||||||
|
|||||||||||||||||||
properties | |||||||||||||||||||
Molar mass | 301.29 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
||||||||||||||||||
density |
1.41 g cm −3 (bulk density) |
||||||||||||||||||
Melting point |
130 ° C |
||||||||||||||||||
Vapor pressure |
400 hPa (20 ° C) |
||||||||||||||||||
solubility |
|
||||||||||||||||||
safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Flutriafol is an active ingredient for crop protection and a 1: 1 mixture of two isomeric chemical compounds from the group of triazoles .
Extraction and presentation
Flutriafol can be obtained from a Friedel-Crafts acylation of fluorobenzene with chloroacetic acid chloride. The resulting intermediate is reacted with a Grignard reagent to a chlorohydrin , which in turn gives flutriafol by condensation with 1,2,4-triazole under basic conditions. An alternative synthesis starts with 2,4'-difluorobenzophenone.
properties
Flutriafol is a colorless solid that is poorly soluble in water.
Stereochemistry
Flutriafol contains one stereocenter and thus forms two enantiomers . The racemate is used , i.e. the 1: 1 mixture of the ( S ) and ( R ) enantiomers.
Enantiomers of flutriafol | |
---|---|
CAS number: 586965-70-0 |
CAS number: 586965-69-7 |
use
Flutriafol is a systemic broad-spectrum fungicide from the triazole group , which is usually used for seed dressing of cereals . It was launched in 1981.
Admission
Flutriafol has been an approved active ingredient in plant protection products in the EU since June 2011. In Switzerland, Austria and Germany, no pesticides are permitted that contain flutriafol as an active ingredient.
Web links
- EU: Review report for the active substance flutriafol (PDF; 192 kB), March 11, 2011
Individual evidence
- ↑ a b c d e f Entry on Flutriafol in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
- ↑ a b c d e f g Flutriafol data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
- ↑ Bruce E. Smart, JC Tatlow: Organofluorine chemistry: principles and commercial applications . 1994, ISBN 978-0-306-44610-8 (English, page 253 in the Google book search).
- ↑ a b Directorate-General for Health and Food Safety of the European Commission: Entry on Flutriafol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.
- ↑ Implementing Directive 2011/42 / EU of the Commission of April 11, 2011 amending Council Directive 91/414 / EEC to include the active substance flutriafol and amending Commission Decision 2008/934 / EC