Isoxaben

Structural formula
General
Surname	Isoxaben
other names	N - [3- (1-Ethyl-1-methylpropyl) isoxazol-5-yl] -2,6-dimethoxy-benzamide ( IUPAC ); N - (3- (1-Ethyl-1-methylpropyl) -1,2-oxazol-5-yl) -2,6-dimethoxy-benzamide; Prolan;
Molecular formula	C 18 H 24 N 2 O 4
Brief description	Colorless, crystalline solid or waxy powder
External identifiers / databases
EC number	407-190-8
ECHA InfoCard	100.100.871
PubChem	73672
ChemSpider	66323
Wikidata	Q2677285
properties
Molar mass	332.39 g mol −1
Physical state	firmly
density	0.58 g cm −3
Melting point	176-179 ° C
boiling point	Decomposes at 200 ° C
Vapor pressure	0.000052 mbar (20 ° C)
solubility	almost insoluble in water (0.93 g l −1 at 20 ° C); 270 g l −1 in acetone ; 98 g l −1 in methanol ;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary	no GHS pictograms
	no GHS pictograms
H and P phrases	H: 413
	P: no P-phrases
Toxicological data	> 10000 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 .

Isoxaben is an organic compound from the benzamide group .

presentation

Isoxaben is produced by methylating 2-ethyl-butyric acid methyl ester with iodomethane in the presence of a base, by further basic reaction with acetonitrile in a Claisen ester condensation , the reaction with hydroxylamine hydrochloride to give the oxime, which cyclizes to isoxazole and esterification with 2,6-dimethoxybenzoyl chloride.

use

Isoxaben is used as a herbicide , it inhibits cellulose synthesis.

Admission

The active ingredient was approved for use as a herbicide in the European Union with effect from June 1, 2011.

In many EU countries, including Germany and Austria, pesticide products with the active ingredient isoxaben are approved (Flexidor, Star Isoxaben), but not in Switzerland.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on isoxaben in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on April 12, 2019.
↑ ^a ^b ^c ^d ^e Entry for CAS no. 82558-50-7 in the GESTIS substance database of the IFA , accessed on March 25, 2013(JavaScript required) .
↑ Entry on Isoxaben (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 13, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . Noyes Publications, Andrew Williams, 1996, ISBN 978-0-8155-1401-5 ( limited preview in Google Book Search).
↑ Directive 2011/32 / EU of the Commission of March 8, 2011 amending Council Directive 91/414 / EEC to include the active substance isoxaben and amending Commission Decision 2008/934 / EC .
↑ General Directorate Health and Food Safety of the European Commission: Entry on isoxaben in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.

[PPDB-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on isoxaben in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on April 12, 2019.

[GESTIS-2] Entry for CAS no. 82558-50-7 in the GESTIS substance database of the IFA , accessed on March 25, 2013(JavaScript required) .

[CLP_100.100.871-3] Entry on Isoxaben (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 13, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[4] Thomas A. Unger: Pesticide Synthesis Handbook . Noyes Publications, Andrew Williams, 1996, ISBN 978-0-8155-1401-5 ( limited preview in Google Book Search).

[5] Directive 2011/32 / EU of the Commission of March 8, 2011 amending Council Directive 91/414 / EEC to include the active substance isoxaben and amending Commission Decision 2008/934 / EC .

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on isoxaben in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.