Trichlorfon

Structural formula
1: 1 mixture of ( S ) -form (left) and ( R ) -form (right)
General
Surname	Trichlorfon
other names	( RS ) - O , O -dimethyl-2,2,2-trichloro-1-hydroxyethyl-phosphonate DEP TCP
Molecular formula	C 4 H 8 Cl 3 O 4 P
Brief description	colorless solid
External identifiers / databases
CAS number 52-68-6 EC number 200-149-3 ECHA InfoCard 100,000,137 PubChem 5853 ChemSpider 5644 Wikidata Q422991
properties
Molar mass	257.44 g mol −1
Physical state	firmly
density	1.73 g cm −3 (20 ° C)
Melting point	77 ° C
boiling point	> 87 ° C (decomposition)
solubility	easily in water (154 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 302-312-317-334-410 P: 261-273-284-302 + 352 + 312-304 + 340-342 + 311
Toxicological data	882 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 .

Trichlorfon is a chiral phosphonate , which as crop protection agents is used.

history

In 1952 Gerhard Schrader and his colleagues found Trichlorfon (TCP) for the first time. Trichlorfon has been used extensively since the 1950s. In 1989 the Kuwaiti general cargo ship Danah lost eight containers filled with Trichlorfon in the North Sea in stormy seas.

use

Trichlorfon is used as an insecticide in agriculture, veterinary medicine, and in the home. It is also used as a raw material in the chemical industry. For example, cattle with skin bumps from a species of fly were treated with TCP. TCP is only slightly toxic in the intestine and has been used in schistosomiasis for some time since 1960 . Trichlorfon was approved in Switzerland against grape moth , groundworm and cabbage flies , for example . In 2007, the EU Commission decided not to include Trichlorfon in the list of approved active ingredients in plant protection products. In Germany, Austria and Switzerland there is no approval as an active ingredient in plant protection products .

safety instructions

Trichlorfon is a contact and food poison. Like all phosphoric acid esters, Trichlorfon is an inhibitor of the cholinesterases acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) and is therefore neurotoxic . At pH = 5.4, TCP splits off hydrogen chloride , producing the even more toxic dichlorvos (DDVP).

Web links

• Entry on Trichlorfon at Vetpharm

Individual evidence

1. ↑ ^{a b c d e f g} Entry on Trichlorfon in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
2. ↑ Entry on Trichlorfon 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. ↑ Trichlorfon data sheet at Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
4. ↑ Eckhard-Herbert Arndt: Load securing as a permanent weak point , THB - daily port report , January 8, 2019.
5. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Trichlorfon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.
6. ^ Entry on Trichlorfon. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.