Diclofop-methyl

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Surname	Diclofop-methyl
other names	( RS ) -Methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate ( IUPAC )
Molecular formula	C 16 H 14 Cl 2 O 4
Brief description	colorless odorless crystals
External identifiers / databases
EC number	257-141-8
ECHA InfoCard	100.051.929
PubChem	39985
ChemSpider	36557
DrugBank	DB13918
Wikidata	Q1210263
properties
Molar mass	341.19 g mol −1
Physical state	firmly
density	1.3 g cm −3
Melting point	39-41 ° C
boiling point	175–176 ° C (0.13 hPa)
solubility	practically insoluble in water
safety instructions
H and P phrases	H: 302-317-410
	P: 273-280-501
Toxicological data	512 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Diclofop-methyl is a selective run-herbicide and the cultivation of wheat and spring barley against wild oats and the cultivation of sugar beet as well as also for the control of wild oats millet used. It belongs to the aryloxyphenoxypropionate class of active ingredients .

history

The market launch took place in the late 1970s by Hoechst AG , which commissioned the first production plant for the herbicide under the brand name Illoxan in the Knapsack Chemical Park in 1979.

Diclofop-methyl is sold under the brand names Illoxan, Hoelon and One Shot and was registered under a patent protection for the company Agrevo (later Bayer CropScience ) until December 31, 2001 .

With the decision of the European Commission of December 5, 2008, diclofop-methyl was to be withdrawn from approval as a pesticide for the European Community by December 31, 2010 at the latest .

In Switzerland, Austria and Germany, diclofop-methyl is no longer or no longer approved as a plant protection product. It can be used in South Tyrol.

effect

By hydrolysis of the actually herbicidal active ingredient, the carboxylic acid is of the ester released after application. It is an inhibitor of the ACCase ( acetyl-CoA-carboxylase ) enzyme .

analysis

Diclofop-methyl can be detected with the help of gas chromatography .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on methyl 2- (4- (2,4-dichlorophenoxy) phenoxy) propionate in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ Entry on methyl 2- (4- (2,4-dichlorophenoxy) phenoxy) propionate 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 .
↑ Rudolf Heitefuss: In plant protection: Basics of practical phytomedicine, 3rd revised and expanded edition, Georg Thieme Verlag Stuttgart ISBN 3-13-513303-6
^ ^A ^b Müfit Bahadir, Harun Parlar, Michael Spiteller: In Springer Umweltlexikon, 2nd edition, Springer Verlag Berlin Heidelberg New York, ISBN 3-540-63561-0 .
↑ chemiepark-knapsack.de: 1970 - 1979 New areas of work in the Hoechst Knapsack plant ( Memento from July 27, 2010 in the Internet Archive ).
↑ Decision of the Commission of December 5, 2008 on the non-inclusion of certain active substances in Annex I of Council Directive 91/414 / EEC (PDF) .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Diclofop in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.
↑ Autonomous Province of Bolzano South Tyrol: Permitted Plant Protection Products Decision of July 1, 2014
^ Hans-Walter Heldt: Plant biochemistry . Elsevier Academic Press 2005, ISBN 0-12-088391-0 .
↑ Depository Services Program of the Canadian Government (PDF; 14 kB).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on methyl 2- (4- (2,4-dichlorophenoxy) phenoxy) propionate in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[CLP_100.051.929-2] Entry on methyl 2- (4- (2,4-dichlorophenoxy) phenoxy) propionate 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] Rudolf Heitefuss: In plant protection: Basics of practical phytomedicine, 3rd revised and expanded edition, Georg Thieme Verlag Stuttgart ISBN 3-13-513303-6

[umweltlexikon-4] A ^b Müfit Bahadir, Harun Parlar, Michael Spiteller: In Springer Umweltlexikon, 2nd edition, Springer Verlag Berlin Heidelberg New York, ISBN 3-540-63561-0 .

[5] rk-knapsack.de: 1970 - 1979 New areas of work in the Hoechst Knapsack plant ( Memento from July 27, 2010 in the Internet Archive ).

[6] Decision of the Commission of December 5, 2008 on the non-inclusion of certain active substances in Annex I of Council Directive 91/414 / EEC (PDF) .

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Diclofop in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[8] Autonomous Province of Bolzano South Tyrol: Permitted Plant Protection Products Decision of July 1, 2014

[9] Hans-Walter Heldt: Plant biochemistry . Elsevier Academic Press 2005, ISBN 0-12-088391-0 .

[10] Depository Services Program of the Canadian Government (PDF; 14 kB).