Tralomethrin

Structural formula
	Structural formula of one of the possible stereoisomers
General
Surname	Tralomethrin
other names	( S ) -α-Cyano-3-phenoxybenzyl (1 R , 3 S ) -2,2-dimethyl-3 - [( RS ) -1,2,2,2-tetrabromethyl] cyclopropanecarboxylate
Molecular formula	C 22 H 19 Br 4 NO 3
Brief description	whitish solid
External identifiers / databases
EC number	266-493-1
ECHA InfoCard	100.060.429
PubChem	48132
Wikidata	Q61446657
properties
Molar mass	665.01 g mol −1
Physical state	firmly
density	1.70 g cm −3
Melting point	138-148 ° C
Vapor pressure	0.048 hPa (25 ° C)
solubility	practically insoluble in water; soluble in acetone (> 1000 g / l), toluene (> 1000 g / l) and ethanol (> 180 g / l);
safety instructions
H and P phrases	H: 302-315-319-410
	P: 273-305 + 351 + 338-501
Toxicological data	> 99 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 .

Tralomethrin is a mixture of several isomeric chemical compounds from the group of pyrethroids .

Extraction and presentation

Tralomethrin can be obtained by reacting methyl chrysanthemate with ozone , carbon tetrabromide , bromine and phenoxycyanobenzyl alcohol .

properties

Tralomethrin is a whitish solid that is practically insoluble in water. It is converted to deltamethrin within a few days by photolysis or metabolically .

Stereochemistry

Tralomethrin is a chiral compound that contains four asymmetrically substituted carbon atoms ( stereocenters ). If no complex synthesis strategies or separation techniques ( diastereomer separation , racemate resolution ) are used, the compound is present as a mixture of the different isomers .

use

Tralomethrin is used as an insecticide . It is used to control a number of insects, particularly Lepidoptera , in cereals, coffee, cotton, fruits, corn, rapeseed, rice, tobacco and vegetables, and is also effective for wood preservation.

Admission

Tralomethrin is not on the list of active ingredients for pesticides permitted in the European Union . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Data sheet Tralomethrin, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 961 ( limited preview in Google Book search).
↑ EPA: Registration Review - Preliminary Problem Formulation for Ecological Risk and Environmental Fate, Endangered Species, and Drinking water Assessments for Tralomethrin ( Memento of April 8, 2013 in the Internet Archive ), March 23, 2010.
↑ ^a ^b 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. 723 ( limited preview in Google Book search).
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
↑ General Directorate Health and Food Safety of the European Commission: Entry on tralomethrin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Data sheet Tralomethrin, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[Thomas_A._Unger-2] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 961 ( limited preview in Google Book search).

[EPA-3] EPA: Registration Review - Preliminary Problem Formulation for Ecological Risk and Environmental Fate, Endangered Species, and Drinking water Assessments for Tralomethrin ( Memento of April 8, 2013 in the Internet Archive ), March 23, 2010.

[Roberts-4] 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. 723 ( limited preview in Google Book search).

[5] Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on tralomethrin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.