Fenoxaprop-P-ethyl

Structural formula
General
Surname	Fenoxaprop-P-ethyl
other names	Ethyl (2 R ) -2- {4 - [(6-chloro-1,3-benzoxazol-2-yl) oxy] phenoxy} propanoate ( IUPAC ) ; Acclaim; Ralon; puma; Whip;
Molecular formula	C 18 H 16 ClNO 5
Brief description	white solid
External identifiers / databases
EC number	615-273-7
ECHA InfoCard	100.113.604
PubChem	91707
ChemSpider	82809
Wikidata	Q16064370
properties
Molar mass	361.78 g mol −1
Physical state	firmly
density	1.32 g cm −3
Melting point	86.5 ° C
boiling point	Decomposition from 260 ° C
Vapor pressure	0.00053 mPa (25 ° C)
solubility	practically insoluble in water (0.7 mg l −1 at 20 ° C); Easily soluble in acetone and ethyl acetate ;
safety instructions
H and P phrases	H: 373-317-410
	P: 273-501
Toxicological data	2360 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 .

Fenoxaprop-P-ethyl is a chemical compound from the aryloxyphenoxypropionate group , which was introduced by Hoechst (now Bayer CropScience ).

Extraction and presentation

Fenoxaprop-ethyl can be prepared starting from propionic acid . This reacts with chlorine , ethanol , hydroquinone and 2-mercapto-6-chlorobenzoxazole to form the end product.

use

Estimated US application rate in 2011

Fenoxaprop-P-ethyl is used as a selective, systemic herbicide against annual monocotyledon weeds such as field foxtail grass , flying oats , millet species and wind stalks , especially in cereal cultivation.

In the cultivation of grain and rice, Fenoxaprop is applied together with the safener Mefenpyr-diethyl (partly also Cloquintocet-mexyl ). In dicotyledon crops such as soybeans, beets, potatoes or rapeseed, it can also be used without a safener.

Fenoxaprop-P-ethyl is an ester that is quickly hydrolyzed to acid, the actual active ingredient, in sensitive plants . It works by inhibiting acetyl-CoA carboxylase (ACCase) in fatty acid biosynthesis.

Admission

Plant protection products with this active ingredient are approved in a number of EU countries, including Austria and Switzerland ( Ralon Super , Puma ).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on Fenoxaprop-P-ethyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 18, 2014.
↑ ^a ^b Datasheet Fenoxaprop-P-ethyl, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ ^a ^b ^c Entry on Fenoxaprop-P-ethyl in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ Entry on (R) -2- [4- (6-chloro-1,3-benzoxazol-2-yloxy) phenoxy] propionic acid ethyl ester Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b entry on fenoxaprop-ethyl. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 768 ( preview ).
↑ General Directorate Health and Food Safety of the European Commission: Entry on Fenoxaprop-P in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[ppdb-1] ↑ ^a ^b ^c ^d ^e ^f Entry on Fenoxaprop-P-ethyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 18, 2014.

[Sigma-2] Datasheet Fenoxaprop-P-ethyl, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[GESTIS-3] Entry on Fenoxaprop-P-ethyl in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CLP_100.113.604-4] Entry on (R) -2- [4- (6-chloro-1,3-benzoxazol-2-yloxy) phenoxy] propionic acid ethyl ester Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[roempp-5] try on fenoxaprop-ethyl. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 768 ( preview ).

[7] General Directorate Health and Food Safety of the European Commission: Entry on Fenoxaprop-P in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.