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Phosphamidon

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This is an old revision of this page, as edited by Beetstra (talk | contribs) at 12:34, 10 August 2011 (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 12:34, 10 August 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Not to be confused with phosphoramidon.
Phosphamidon
Names
IUPAC name (E/Z)- dimethyl phosphate
Other names Dimecron
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.032.818 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CCN(CC)C(=O)C(=C(C)OP(=O)(OC)OC)Cl
Properties
Chemical formula C10H19ClNO5P
Molar mass 299.69 g·mol
Density 1.2132 g/cm
Melting point 120-123 °C
Boiling point 162 °C (1.5 mmHg)
Solubility in water Miscible
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose) 13 mg/kg (mouse, oral)
6 mg/kg (mouse, IV)
20 mg/kg (rat, oral)
26 mg/kg (rat, subcut.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Phosphamidon is an organophosphate insecticide first reported in 1960. It acts as a cholinesterase inhibitor.

The commercial product typically exists as a mixture of 70% (Z)-isomer and 30% (E)-isomer.

Toxicity and regulation

Phosphamidon is very highly toxic to mammals and is listed as WHO Hazard Class Ia. A harvester developed symptoms of moderately severe poisoning after working in a field that had been sprayed with the chemical 2 weeks earlier. He collapsed and exhibited significant depression of serum cholinesterase, but recovered completely within 2 days after successful treatment with atropine. International trade of phosphamidon is covered by the Rotterdam Convention.

References

  1. ^ Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
  2. ^ Jacques, R.; Bein, H. J. (1960). "Toxicology and pharmacology of a new systemic phosphoric acid ester insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate)". Archiv fuer Toxikologie. 18: 316–330.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg. 2: P1153-1155.
  4. S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Brit. J. Ind. Med. 22: 236-239, 1965.
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