Phosalone

Structural formula
General
Surname	Phosalone
other names	Trade names: Azofene, Rubitox, Zolone, Benzphos, Benzophosphate, NIAGARA 9241; S -6-chloro-2,3-dihydro-2-oxobenzoxazol-3-ylmethyl- O , O -diethylphosphorodithioate ( IUPAC );
Molecular formula	C 12 H 15 ClNO 4 PS 2
Brief description	colorless solid with a garlic-like odor
External identifiers / databases
EC number	218-996-2
ECHA InfoCard	100.017.270
PubChem	4793
Wikidata	Q413116
properties
Molar mass	367.8 g mol −1
Physical state	firmly
density	1.39 g cm −3
Melting point	47.5-48 ° C
solubility	almost insoluble in water (3 mg l −1 at 25 ° C); soluble in many organic solvents;
safety instructions
H and P phrases	H: 301-312-332-317-410
	P: 273-280-301 + 310-501
Toxicological data	20–36 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 .

Phosalone is an aromatic dithiophosphoric acid ester and a carbamate that has been widely used as an insecticide and acaricide . Phosalon was introduced in 1963 by Rhône-Poulenc (now Bayer CropScience ). A structurally very similar insecticide is the azamethiphos .

Extraction and presentation

Phosalone can be obtained from 2-aminophenol and urea . These condense to benzoxazolone , which is then chlorinated . With formaldehyde and hydrogen chloride , a chloromethyl group is added to the nitrogen atom. In the last step, the intermediate reacts with DEPA to form phosalone.

properties

Phosalone forms flammable, white crystals and has a characteristic, garlic-like odor. It is quickly absorbed in the body, where it is converted into a more potent oxo analog relatively quickly.

Admission

The compound was withdrawn from approval as a plant protection product in the EU in December 2006 due to the risks to humans . There are no longer any approvals for phosalone-containing pesticides in Switzerland, Germany and Austria.

safety instructions

Like most phosphoric acid esters, phosalone is a neurotoxin which, by blocking important enzymes such as cholinesterases , causes damage to the central nervous system as well as the lungs, liver and kidneys.

Individual evidence

↑ ^a ^b EPA Pesticide Fact Sheet: Phosalone .
↑ ^a ^b ^c ^d Entry on Phosalone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Data sheet Phosalone at Extoxnet.
↑ Entry on Phosalone 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 Joint Meeting on Pesticide Residues (JMPR), Monograph for Phosalone , accessed December 9, 2014.
^ Entry on Phosalone. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2015.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 431 ( limited preview in Google Book search).
↑ DECISION OF THE COMMISSION of December 22, 2006 on the non-inclusion of phosalone in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products containing this active substance (PDF) .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Phosalone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 11, 2016.

[cor-1] EPA Pesticide Fact Sheet: Phosalone .

[GESTIS-2] Entry on Phosalone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[3] Data sheet Phosalone at Extoxnet.

[CLP_100.017.270-4] Entry on Phosalone 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 .

[inchem-5] Joint Meeting on Pesticide Residues (JMPR), Monograph for Phosalone , accessed December 9, 2014.

[roempp-6] Entry on Phosalone. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2015.

[unger-7] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 431 ( limited preview in Google Book search).

[8] DECISION OF THE COMMISSION of December 22, 2006 on the non-inclusion of phosalone in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products containing this active substance (PDF) .

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on Phosalone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 11, 2016.