Trifluralin

Structural formula
General
Surname	Trifluralin
other names	α, α, α-trifluoro-2,6-dinitro- N , N -dipropyl- p -toluidine
Molecular formula	C 13 H 16 F 3 N 3 O 4
Brief description	yellow-orange solid with an aromatic odor
External identifiers / databases
CAS number 1582-09-8 EC number 216-428-8 ECHA InfoCard 100.014.936 PubChem 5569 ChemSpider 5368 Wikidata Q418247
properties
Molar mass	335.28 g mol −1
Physical state	firmly
density	1.36 g cm −3
Melting point	46-47 ° C
boiling point	140 ° C (at 4 h Pa )
solubility	almost insoluble in water (<0.1 mg l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 351-317-410 P: 261-273-280-304 + 340 + 312-333 + 313-403 + 233
Toxicological data	0.0084–54.4 mg l −1 ( LC 50 ,  fish , 96 hours ) 0.05–5.6 mg l −1 ( LC 50 ,  Crustacea , 48 hours )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trifluralin is an active ingredient for crop protection and a chemical compound from the group of aromatic and fluorinated amino compounds and nitro compounds .

history

Trifluralin was launched by Eli Lilly in the 1960s . Up to 2006, around 6,000 tonnes per year were produced in the EU.

Extraction and presentation

Trifluralin can be obtained in a multi-stage process from 4-chlorobenzotrifluoride (by reaction with nitric acid ) or 4-trifluoromethyl-2,6-dinitrochlorobenzene and dipropylamine .

use

Trifluralin is used as a selective soil herbicide . There were approvals in winter and summer oilseed rape, sunflowers, stubble, cabbage and swede. Application rates of 960 to 1440 g / ha were used. The agent had to be worked flat into the floor after application. This largely prevented the active substance from evaporating and its degradation via ultraviolet radiation . On September 20, 2007, the approval in the EU was revoked. In Switzerland, several trifluralin preparations were approved for use against monocotyledonous and dicotyledonous weeds.

In the EU states like Germany and Austria as well as in Switzerland there is no longer any approval.

safety instructions

Trifluralin is suspected of having a carcinogenic effect. It is very toxic to aquatic organisms.

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on trifluralin in the GESTIS substance database of the IFA , accessed on February 21, 2017(JavaScript required) .
2. ↑ Entry on trifluralin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
3. ↑ Trifluralin data sheet from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
4. ↑ US Patent 3257190, Method of eliminating weed grasses and broadleaf weeds June 21, 1966 .
5. ↑ ^{a b} Emission reduction for priority and priority hazardous substances of the Water Framework Directive - material data sheets - data sheet Trifluralin , texts 29/07, environmental research plan of the Federal Minister for the Environment, Nature Conservation and Nuclear Safety, p. 479.
6. ↑ Shreve, R. Norris, Chemical Process Industries, 4th Edition, 1977, pp. 431-432, ISBN 0-07-057145-7 .
7. ↑ on the non-inclusion of trifluralin in Annex I of the Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF) .
8. ↑ General Directorate Health and Food Safety of the European Commission: Entry on trifluralin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.