Penflufen

Structural formula
Structural formula without stereochemistry
General
Surname	Penflufen
other names	2 '- [( RS ) -1,3-dimethylbutyl] -5-fluoro-1,3-dimethylpyrazole-4-carboxanilide N - [2- (1,3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1 H -pyrazole-4-carboxamide
Molecular formula	C 18 H 24 FN 3 O
Brief description	dirty white powder
External identifiers / databases
CAS number 494793-67-8 (racemate) 856017-53-3 ( S ) -Penflufen 2095486-79-4 ( R ) -Penflufen EC number 619-823-7 ECHA InfoCard 100.113.711 PubChem 11674113 Wikidata Q16736519
properties
Molar mass	317.40 g mol −1
Physical state	firmly
Melting point	111 ° C
boiling point	decomposes above 320 ° C
solubility	practically insoluble in water (10.9 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 410 P: 273-501
Toxicological data	> 2000 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 .

Penflufen is a chemical compound from the group of pyrazole-4-carboxamides , which is used as a fungicide for dressing seeds .

Stereochemistry

Penflufen has a stereocenter , is chiral and accordingly forms two enantiomers . The racemate is used , i.e. the 1: 1 mixture of the ( S ) and the ( R ) enantiomer.

Enantiomers of Penflufen
( S ) -Penflufen	( R ) -Penflufen

effect

The compound works by inhibiting succinate dehydrogenase .

use

Penflufen is used under the trade name Emesto in potato cultivation against silver scab ( Helminthosporium ), dry rot ( Fusarium ) and soil-borne diseases such as root killer disease ( Rhizoctonia solani ) and as EverGol in rapeseed, soybeans, maize, grain, cotton and rice.

Admission

In some EU countries, including Germany and Austria, plant protection products with this active ingredient are approved, but not in Switzerland.

Individual evidence

1. ↑ ^{a b c d e} Entry on Penflufen in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on October 13, 2014.
2. ↑ ^{a b} data sheet Penflufen at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
3. ↑ ^{a b} Directorate-General for Health and Food Safety of the European Commission: Entry on Penflufen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.