Flutriafol

Structural formula
Simplified structural formula without stereochemistry
General
Surname	Flutriafol
other names	( RS ) -2,4'-Difluoro-α- (1 H -1,2,4-triazol-1-ylmethyl) benzhydrylethanol (±) -2,4'-Difluoro-α- (1 H -1,2,4-triazol-1-ylmethyl) benzhydrylethanol
Molecular formula	C 16 H 13 F 2 N 3 O
Brief description	colorless solid
External identifiers / databases
CAS number 76674-21-0 EC number 616-367-0 ECHA InfoCard 100.108.517 PubChem 91727 ChemSpider 82827 Wikidata Q1434425
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	practically insoluble in water (0.095 g l −1 at 20 ° C) easily soluble in acetone (116 g l −1 ) and methanol (115 g l −1 )
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	1140 mg kg −1 ( LD 50 ,  rat ,  oral ) > 2000 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
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

1. ↑ ^{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.
2. ↑ ^{a b c d e f g} Flutriafol data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
3. ↑ 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).
4. ↑ ^{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.
5. ↑ 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