Fenpropidin

Structural formula
	1: 1 mixture of ( R ) -form (top) ; and ( S ) -form (bottom)
General
Surname	Fenpropidin
other names	( RS ) -1- [3- (4- tert -Butylphenyl) -2-methylpropyl] piperidine ( IUPAC ); (±) -1- [3- (4- tert -Butylphenyl) -2-methylpropyl] piperidine; ( RS ) -1- [3- [4- (1,1-Dimethylethyl) phenyl] -2-methylpropyl] piperidine; (±) -1- [3- [4- (1,1-Dimethylethyl) phenyl] -2-methylpropyl] piperidine;
Molecular formula	C 19 H 31 N
Brief description	yellowish liquid
External identifiers / databases
EC number	614-049-6
ECHA InfoCard	100.116.750
PubChem	91694
ChemSpider	82797
DrugBank	DB12728
Wikidata	Q64825
properties
Molar mass	273.46 g mol −1
Physical state	liquid
density	0.92 g cm −3
Melting point	−64.8 ° C
boiling point	100 ° C at <0.001 hPa; 243 ° C (decomposition);
Vapor pressure	17 mPa (25 ° C)
solubility	very slightly soluble in water (530 mg l −1 at 25 ° C); soluble in heptane, xylene, acetone and ethyl acetate;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-319
	P: 280-305 + 351 + 338
Toxicological data	1,447 mg kg −1 ( LD 50 , rat , oral ) ; 1,820 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 .

Fenpropidin is a mixture of two enantiomeric chemical compounds from the group of piperidines .

Extraction and presentation

Fenpropidine can be obtained by reacting p - tert- butylbenzaldehyde with propionaldehyde , piperidine and hydrogen .

properties

Fenpropidin is a yellowish liquid that is very sparingly soluble in water. The compound is stable to hydrolysis and UV light.

use

Fenpropidin, launched in 1986, is used as a fungicide mainly on cereals. In combination with difenoconazole , it is also used in sugar beet and fodder beet to combat leaf diseases. The effect is based (similar to that of morpholines ) on the inhibition of the ergosterol biosynthesis.

Admission

Fenpropidin has been an approved active ingredient in pesticides in the countries of the European Union since January 2009 for use as a fungicide. In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

literature

EU: Review of the existing maximum residue levels (MRLs) for fenpropidin according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 9, 2011, p. 2333, doi : 10.2903 / j.efsa.2011.2333 .

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on fenpropidin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet fenpropidin from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
^ ^A ^b ^c Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 1232 ( limited preview in Google Book search).
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 497 ( limited preview in Google Book search).
^ Horst Börner: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49067-1 , pp. 530 ( limited preview in Google Book search).
↑ Directive 2008/66 / EC of the Commission of June 30, 2008 amending Council Directive 91/414 / EEC to include the active substances bifenox, diflufenican, fenoxaprop-P, fenpropidin and quinoclamine (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on fenpropidin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[PPDB-1] Entry on fenpropidin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet fenpropidin from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[Roberts-3] A ^b ^c Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 1232 ( limited preview in Google Book search).

[Unger-4] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 497 ( limited preview in Google Book search).

[Horst_Börner-5] Horst Börner: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49067-1 , pp. 530 ( limited preview in Google Book search).

[6] Directive 2008/66 / EC of the Commission of June 30, 2008 amending Council Directive 91/414 / EEC to include the active substances bifenox, diflufenican, fenoxaprop-P, fenpropidin and quinoclamine (PDF)

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on fenpropidin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.