Diflufenican

Structural formula
General
Surname	Diflufenican
other names	N - (2,4-Difluorophenyl) -2- [3- (trifluoromethyl) phenoxy] nicotinamide ( IUPAC ) N - (2,4-difluorophenyl) -2- (3- (trifluoromethyl) phenoxy) -3-pyridinecarboximide 2 ′, 4′-difluoro-2- (α, α, α-trifluor- m -tolyloxy) nicotinanilide
Molecular formula	C 19 H 11 F 5 N 2 O 2
Brief description	colorless solid
External identifiers / databases
CAS number 83164-33-4 EC number 617-446-2 ECHA InfoCard 100.122.360 PubChem 91735 ChemSpider 82834 Wikidata Q424793
properties
Molar mass	394.30 g mol −1
Physical state	firmly
Melting point	160 ° C
solubility	practically insoluble in water
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302 + 312-412 P: 273-280-301 + 312 + 330-302 + 352 + 312
Toxicological data	2000 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diflufenican is a chemical compound from the group of carboxamides , anilines and pyridines, or more precisely the phenoxynicotinanilides.

Extraction and presentation

Diflufenican can be obtained through a multi-stage reaction of nicotinic acid with chlorine , 3-trifluoromethylphenol , thionyl chloride and 2,4-difluoroaniline .

properties

Diflufenican is a colorless solid that is practically insoluble in water.

use

Diflufenican is used as an active ingredient in herbicides. It is mainly absorbed through the soil, which leads to the death of the weed plants. Diflufenican remains effective for several weeks if there is sufficient soil moisture. It works primarily by inhibiting carotene biosynthesis and secondarily by increasing the breakdown of chlorophyll. The compound is stable in solution and against the effects of light and temperature. It is preferably used in autumn as a herbicide for winter cereals, especially pre-emergence and early post-emergence .

Admission

In many EU countries, including Germany and Austria, as well as Switzerland, plant protection products that contain this active ingredient are approved.

Trade names

Lyskamm, Loredo, Alister, Azur, Brodal, Capture, Cougar, Fenikan, First, Harpo Z, Herold, Javelin, Laureat, Panther, Quartz GT, Quartz S, Quartz Super, Tigrex, Viper Compact

Individual evidence

1. ↑ ^{a b c} M. Bahadir, H. Parlar, Michael Spiteller: Springer Umweltlexikon . ( Page 321 in Google Book Search).
2. ↑ ^{a b c d e f g h} Entry on diflufenican in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .
3. ↑ Entry on N- (2,4-difluorophenyl) -2- [3- (trifluoromethyl) phenoxy] -3-pyridinecarboxamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturer or distributor can expand the harmonized classification and labeling .
4. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 20 in the Google book search).
5. ↑ Data sheet Diflanil 500 SC  ( page no longer available , search in web archives )  Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. at Plantan, accessed on June 29, 2017 (PDF).  
6. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Diflufenican in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.