Propanil

Structural formula
General
Surname	Propanil
other names	N - (3,4-dichlorophenyl) propionamide; 3 ', 4'-dichloropropionanilide; DCPA;
Molecular formula	C 9 H 9 Cl 2 NO
Brief description	brown solid with a characteristic odor
External identifiers / databases
EC number	211-914-6
ECHA InfoCard	100.010.832
PubChem	4933
Wikidata	Q413507
properties
Molar mass	218.18 g mol −1
Physical state	firmly
density	1.41 g cm −3 (22 ° C)
Melting point	91-93 ° C
solubility	very poorly soluble in water (0.13 g l −1 at 20 ° C); soluble in ethanol and chlorobenzene ;
safety instructions
H and P phrases	H: 302-400
	P: 273-301 + 312 + 330
Toxicological data	367 mg kg −1 ( LD 50 , rat , oral ) ; 4830 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propanil is a chemical compound from the group of carboxamides and organic chlorine compounds , a so-called anilide .

history

Propanil was launched in 1962 by Rohm and Haas . A Monsanto patent claim was filed in the Monsanto Co. v. Rohm and Haas Co. refused.

Extraction and presentation

Propanil can be obtained by many of the common organic synthetic methods used to make amides . Industrially, it is obtained from o- dichlorobenzene , which is nitrated, hydrogenated and esterified with propionyl chloride.

properties

Propanil is stable in emulsion concentrates, but hydrolyses in acidic and alkaline media to 3,4-dichloroaniline and propionic acid .

use

Uses of Propanil in the US

Propanil is used as a herbicide to control dicotyledonous weeds and grasses in rice cultivation, whereby their photosystem II is inhibited (rice metabolizes propanil quickly and is therefore insensitive). In the USA it is one of the most frequently used herbicides (2011: 2000 t per year).

Admission

In the EU, the approval was withdrawn in September 2008. As a result, no plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Web links

GC / MS-Determination of 3,4-Dichloroaniline as a Metabolite of Selected Herbicides (TU Dresden)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on propanil in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c Poisons Information Monograph (PIM) for Propanil , accessed December 9, 2014.
↑ Entry on Propanil in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
^ ^A ^b Robert E. Hoagland, JK Norsworthy, F. Carey, RE Talbert: Metabolically based resistance to the herbicide propanil in Echinochloa species . In: Weed Science . tape 52 , no. 3 , June 2004, p. 475-486 , doi : 10.1614 / WS-03-039R .
↑ Decision 2008/769 / EC of the Commission of September 30, 2008 (PDF) on the non-inclusion of propanil in Annex I of Council Directive 91/414 / EEC and the revocation of the approvals for plant protection products with this substance (PDF; 51 kB) .
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Propanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 27, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on propanil in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[inchem-2] Poisons Information Monograph (PIM) for Propanil , accessed December 9, 2014.

[CLP_100.010.832-3] Entry on Propanil in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[resistance-4] A ^b Robert E. Hoagland, JK Norsworthy, F. Carey, RE Talbert: Metabolically based resistance to the herbicide propanil in Echinochloa species . In: Weed Science . tape 52 , no. 3 , June 2004, p. 475-486 , doi : 10.1614 / WS-03-039R .

[5] Decision 2008/769 / EC of the Commission of September 30, 2008 (PDF) on the non-inclusion of propanil in Annex I of Council Directive 91/414 / EEC and the revocation of the approvals for plant protection products with this substance (PDF; 51 kB) .

[6] Directorate-General for Health and Food Safety of the European Commission: Entry on Propanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 27, 2016.