Isoxathione

Structural formula
General
Surname	Isoxathione
other names	O , O -Diethyl- O- (5-phenylisoxazol-3-yl) thiophosphate; Karphos;
Molecular formula	C 13 H 16 NO 4 PS
Brief description	light yellow liquid
External identifiers / databases
EC number	242-624-8
ECHA InfoCard	100.038.734
PubChem	29307
Wikidata	Q426373
properties
Molar mass	313.33 g mol −1
Physical state	liquid
density	1.23 g cm −3
boiling point	160 ° C at 0.20 hPa
Vapor pressure	0.133 mPa (25 ° C)
solubility	practically insoluble in water (1.9 mg l −1 at 25 ° C)
safety instructions
H and P phrases	H: 301 + 311-410
	P: 273-280-301 + 310-312-501
Toxicological data	112 mg kg −1 ( LD 50 , rat , oral ) ; 450 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 .

Isoxathion is an active ingredient for crop protection and a chemical compound from the group of isoxazoles and thiophosphoric acid esters .

presentation

Isoxathione can be obtained by reacting diethyl chlorothiophosphate with 3-hydroxy-5-phenylisoxazole . The latter is obtained by reacting hydroxymethylacetophenone with nitric acid and sodium hydroxide.

properties

Isoxathione is a light yellow liquid that is practically insoluble in water.

use

Isoxathion is used as an insecticide and belongs to the group of phosphoric acid esters . It was first introduced in Japan in 1972 by the Sankyo company under the trade name Karphos and was mainly used for citrus fruits . It works by inhibiting acetylcholinesterase . It is unstable under alkaline conditions and decomposes to 3-hydroxy-5-phenylisoxazole.

Admission

In the EU states including Germany and Austria as well as in Switzerland, no pesticides with isoxathione as an active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on isoxathione in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
↑ ^a ^b ^c ^d ^e Entry on O, O-Diethyl-O- (5-phenylisoxazol-3-yl) thiophosphate in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on O, O-diethyl O-5-phenylisoxazol-3-ylphosphorothioate 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 .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 327 in the Google book search).
^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 356 in Google book search).
↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on isoxathione in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[herts-1] ↑ ^a ^b ^c ^d ^e ^f Entry on isoxathione in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

[GESTIS-2] Entry on O, O-Diethyl-O- (5-phenylisoxazol-3-yl) thiophosphate in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.038.734-3] Entry on O, O-diethyl O-5-phenylisoxazol-3-ylphosphorothioate 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 .

[unger-4] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 327 in the Google book search).

[Roberts-5] Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 356 in Google book search).

[6] Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF)

[7] General Directorate Health and Food Safety of the European Commission: Entry on isoxathione in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.