Fenoprop

Structural formula
1: 1 mixture of the ( R ) -form (left) and the ( S ) -form (right)
General
Surname	Fenoprop
other names	( RS ) -2- (2,4,5-trichlorophenoxy) propionic acid Silvex 2,4,5-TP
Molecular formula	C 9 H 7 Cl 3 O 3
Brief description	colorless solid
External identifiers / databases
CAS number 93-72-1 EC number 202-271-2 ECHA InfoCard 100.002.066 PubChem 7158 ChemSpider 6891 Wikidata Q3092689
properties
Molar mass	269.51 g mol −1
Physical state	firmly
density	1.21 g cm −3 (bulk density)
Melting point	179-181 ° C
pK s value	2.84
solubility	sparingly soluble in water (176 mg l −1 at 25 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302-315-410 P: 273-501
Toxicological data	> 3200 mg kg −1 ( LD 50 ,  rabbit ,  transdermal ) 650 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 .

Fenoprop is an active ingredient in pesticides from the group of chlorinated carboxylic acids or phenoxypropionic acids. There are two isomers, the ( R ) form and the ( S ) form. Fenoprop is a 1: 1 mixture ( racemate ) of the ( R ) form and the ( S ) form.

Extraction and presentation

Fenoprop can be obtained by reacting 2,4,5-trichlorophenol with sodium α-chloropropionate .

It is also possible to use propionic acid and phenol , which react with chlorine to form 2-chloropropionic acid and 2,4-dichlorophenol , which are converted to fenoprop.

properties

Fenoprop is a colorless solid. It decomposes when heated.

use

Fenoprop and its derivatives have been used as a herbicide and growth regulator. Its use has been banned in the USA since 1985. In the Federal Republic of Germany it was approved between 1971 and 1974. The activity as a plant growth regulator of salts of the compound was first published in 1945 and in 1953 Dow Chemical brought an ester of the compound on the market.

Admission

No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Derived connections

The CAS number in brackets.

• Fenoprop-butomethyl (2317-24-0)
• Fenoprop-butotyl (19398-13-1)
• Fenoprop-3-butoxypropyl (25537-26-2)
• Fenoprop-butyl (13557-98-7)
• Fenoprop-isoctyl (32534-95-5)
• Fenoprop-methyl (4841-20-7)
• Fenoprop Potassium (2818-16-8)

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry for CAS no. 93-72-1 in the GESTIS substance database of the IFA , accessed on June 29, 2015(JavaScript required) .
2. ↑ ^{a b} Entry on Fenoprop in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on June 29, 2015.
3. ↑ Entry on Fenoprop 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 .
4. ^ Entry on Fenoprop in the Hazardous Substances Data Bank , accessed June 29, 2015.
5. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 978-0-8155-1853-2 , pp. 763 ( limited preview in Google Book search).
6. ↑ EPA: Consumer Fact Sheet
7. ^ Peter Brandt: Reports on Plant Protection Products 2009 Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer-Verlag, 2010, ISBN 978-3-0348-0029-7 , pp. 16 ( limited preview in Google Book search).
8. ↑ Wayland J. Hayes, Jr .: Classes of Pesticides . Elsevier, 2013, ISBN 978-1-4832-8863-5 , pp. 1336 ( limited preview in Google Book search).
9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Fenoprop in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.