Fenoxanil

Structural formula
Structural formula without representation of the stereochemistry
General
Surname	Fenoxanil
other names	N - (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propionamide
Molecular formula	C 15 H 18 Cl 2 N 2 O 2
Brief description	white solid
External identifiers / databases
CAS number 115852-48-7 EC number 601-390-0 ECHA InfoCard 100.120.651 PubChem 11262655 ChemSpider 9437670 Wikidata Q19279547
properties
Molar mass	329.22 g mol −1
Physical state	firmly
density	1.22 g cm −3
Melting point	69-72.5 ° C
solubility	practically insoluble in water (30 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	> 5000 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 .

Fenoxanil is a mixture of numerous stereoisomeric chemical compounds from the group of propionamides and a fungicide introduced by BASF and Nihon Nohyaku around 2000 .

use

Fenoxanil is a protective fungicide with systemic effects. It works by inhibiting melanin biosynthesis against rice blotch fungus ( Magnaporthe oryzae ). The commercial product consists of a mixture of four isomers: 85% ( R , RS ) and 15% ( S , RS ).

Stereochemistry

Fenoxanil contains two stereocenters . In general, chemical compounds with several stereocenters form up to 2 ⁿ stereoisomers. Here n is the number of stereocenters. According to this, there are four stereoisomers of fenoxanil, which have also been confirmed experimentally:

Stereoisomers of fenoxanil
CAS number: 143784-54-7	CAS number: 143784-51-4
CAS number: 143784-52-5	CAS number: 143784-53-6

Admission

Fenoxanil is not approved as a crop protection agent in the European Union or Switzerland .

See also

• Carpropamide
• Diclocymet

Individual evidence

1. ↑ ^{a b c d e f g} Entry on Fenoxanil. In: Römpp Online . Georg Thieme Verlag, accessed on January 6, 2015.
2. ↑ ^{a b c d} data sheet fenoxanil from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
3. ↑ Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.
4. ↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 10.
5. ^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 25, 2016.