Bromethalin

Structural formula
General
Surname	Bromethalin
other names	N -methyl-2,4-dinitro-6- (trifluoromethyl) - N - (2 ', 4', 6'-tribromophenyl) aniline
Molecular formula	C 14 H 7 Br 3 F 3 N 3 O 4
Brief description	white to slightly yellowish odorless solid
External identifiers / databases
CAS number 63333-35-7 EC number 613-202-4 ECHA InfoCard 100.109.042 PubChem 44465 ChemSpider 40463 Wikidata Q421626
properties
Molar mass	577.93 g mol −1
Physical state	firmly
Melting point	150-151 ° C
solubility	almost insoluble in water soluble in chloroform and acetone moderately soluble in aromatic hydrocarbons
safety instructions
GHS hazard labeling no classification available
Toxicological data	3.7 mg kg −1 ( LD 50 ,  dog ,  oral ) 0.54 mg kg −1 ( LD 50 ,  cat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bromethalin is a chemical compound from the aniline group .

Extraction and presentation

Bromethalin can be obtained by a multi-stage reaction of toluene with chlorine , hydrogen fluoride , nitric acid , aniline , dimethyl sulfate and dibromoisocyanuric acid, see the following synthesis scheme :

properties

Bromethalin is a white, odorless solid that is insoluble in water and decomposes when exposed to UV light .

use

Bromethalin is used as a rodenticide . It was launched in 1985. Bromethalin does not belong to the group of active substances called vitamin K antagonists (like the 4-hydroxycoumarins warfarin and bromadiolone ). After ingestion, it is largely converted in the liver to desmethylbromethalin , which is significantly more toxic than the starting substance. This decouples the oxidative phosphorylation in the mitochondria of the cells, which causes edema mainly in the brain and spinal cord.

Admission

In the states of the EU, including Germany and Austria, as well as in Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on bromethalin in the Hazardous Substances Data Bank , accessed on September 27, 2012.
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ↑ ^{a b c} vetpharm: Bromethalin in small animals
4. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 861 ( limited preview in Google Book search).
5. ↑ Aspcapro: Bromethalin: The other rodenticide ( Memento of the original from May 5, 2014 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 181 kB). 
6. ↑ Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 908 ( limited preview in Google Book search).
7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on bromethalin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.