Chlomethoxyfen

Structural formula
General
Surname	Chlomethoxyfen
other names	Chlomethoxynil; Diphenex; Ekkusugon; 2,4-dichloro-1- (3-methoxy-4-nitrophenoxy) benzene; 5- (2,4-dichlorophenoxy) -2-nitroanisole;
Molecular formula	C 13 H 9 Cl 2 NO 4
External identifiers / databases
EC number	251-266-1
ECHA InfoCard	100,046,591
PubChem	36250
Wikidata	Q15726992
properties
Molar mass	314.12 g mol −1
Physical state	firmly
density	1.37 g cm −3
Melting point	113 ° C
Vapor pressure	1.87 mPa (25 ° C)
solubility	practically insoluble in water (0.0003 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	> 18000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlomethoxyfen is a chemical compound from the group of diphenylether herbicides . The contact herbicide is a protoporphyrinogen oxidase inhibitor and acts on the young shoots, leaves and partly on the roots of broad-leaved weeds and grasses. It is used in rice cultivation to control barnacles , cornices and annual broadleaf weeds. Between 1975 and 1985 it was one of the most important herbicidal active ingredients there.

Extraction and presentation

Chlomethoxyfen is presented starting from anisole . This is chlorinated and nitrated with nitric acid . The 3-chloro-6-nitroanisole then reacts with 2,4-dichlorophenol to form chloromethoxyfen.

Admission

The use of the active ingredient chlomethoxyfen in plant protection products is not 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 Entry on chlomethoxyfen in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on February 13, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Peter Böger, Ko Wakabayashi: Peroxidizing Herbicides . Springer, 1999, ISBN 3-540-64550-0 , pp. 359 ( limited preview in Google Book Search).
↑ Bruce Archibald Auld and Kil-Ung Kim (eds.): Weed Management in Rice . FAO, 1996, p. 222 ( limited preview in Google Book search).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 909 ( limited preview in Google Book search).
↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.
↑ General Directorate Health and Food Safety of the European Commission: Entry on chlomethoxyfen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 17, 2016.

[ppdb-1] ↑ ^a ^b ^c ^d ^e ^f Entry on chlomethoxyfen in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on February 13, 2014.

[NV-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.

[perox-3] Peter Böger, Ko Wakabayashi: Peroxidizing Herbicides . Springer, 1999, ISBN 3-540-64550-0 , pp. 359 ( limited preview in Google Book Search).

[4] Bruce Archibald Auld and Kil-Ung Kim (eds.): Weed Management in Rice . FAO, 1996, p. 222 ( limited preview in Google Book search).

[unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 909 ( limited preview in Google Book search).

[6] Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on chlomethoxyfen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 17, 2016.