Napropamide

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Structural formula
Napropamide structural formula
1: 1 mixture of ( R ) - and ( S ) -enantiomer -
structural formula without stereochemistry
General
Surname Napropamide
other names
  • Devrinol
  • ( RS ) - N , N -diethyl-2- (1-naphthyloxy) propanamide
  • (±) - N , N -diethyl-2- (1-naphthyloxy) propanamide
  • rac - N , N -diethyl-2- (1-naphthyloxy) propanamide
Molecular formula C 17 H 21 NO 2
Brief description

colorless odorless crystals

External identifiers / databases
CAS number 15299-99-7
EC number 239-333-3
ECHA InfoCard 100.035.742
PubChem 127189
Wikidata Q17578703
properties
Molar mass 271.35 g mol −1
Physical state

firmly

Melting point
  • 75 ° C
  • technical 68-70 ° C
solubility

practically insoluble in water (73 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 .

Napropamid is a chemical compound from the group of acetamides . It was introduced as a herbicide by Stauffer Chemical in 1971 .

Extraction and presentation

Napropamid can be prepared starting from propionic acid . This is brominated and reacts with thionyl chloride . The intermediate product reacts further with diethylamine and 2-naphthol to form napropamide.

use

Napropamid is used as a selective pre-emergence herbicide against weeds and weeds in winter rape, fruit, vegetable and ornamental plant cultivation. In rapeseed cultivation, it is partly introduced into the soil by pre-sowing.

Napropamid is one of the soil herbicides and acts as a fatty acid synthesis inhibitor (VLCFA inhibitor).

Admission

In Germany, Austria, Switzerland and other EU countries, plant protection products with napropamide as an active ingredient are approved.

literature

  • Alfonso Salinas-Castillo, Jorge Fernando Fernandez-Sanchez, Antonio Segura-Carretero, Alberto Fernandez-Gutierrez: Simple determination of the herbicide napropamide in water and soil samples by room temperature phosphorescence . In: Pest Management Science . tape 61 , no. 8 , August 2005, p. 816-820 , doi : 10.1002 / ps.1054 .
  • Allan Walker, Nisha R. Parekh, Steven J. Roberts, Sarah J. Welch: Evidence for the enhanced biodegradation of napropamide in soil . In: Pesticide Science . tape 39 , no. 1 , 1993, p. 55-60 , doi : 10.1002 / ps.2780390108 .

Individual evidence

  1. ↑ a b c d e f g Entry on napropamide. In: Römpp Online . Georg Thieme Verlag, accessed on July 28, 2014.
  2. ↑ a b Napropamid data sheet from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
  3. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 41 ( limited preview in Google Book search).
  4. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on napropamide in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 14, 2016.