Phosphamidon

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Not to be confused with phosphoramidon.
Phosphamidon
IUPAC name

(E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate

Other names

Dimecron

Identifiers
CAS number 13171-21-6, 
297-99-4 (E)
23783-98-4 (Z)
PubChem 25750
UNII 7H857A6N6H YesY
KEGG C18689 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H19ClNO5P
Molar mass 299.69 g mol−1
Density 1.2132 g/cm3[1]
Melting point 120-123 °C[2]
Boiling point 162 °C (1.5 mmHg)[3]
Solubility in water Miscible
Hazards
LD50 13 mg/kg (mouse, oral)[2]
6 mg/kg (mouse, IV)[2]
20 mg/kg (rat, oral)[2]
26 mg/kg (rat, subcut.)[2]
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Phosphamidon is an organophosphate insecticide first reported in 1960.[2][3] It acts as a cholinesterase inhibitor.

The commercial product typically exists as a mixture of 70% (Z)-isomer and 30% (E)-isomer.[1]

Toxicity and regulation

Phosphamidon is very highly toxic to mammals and is listed as WHO Hazard Class Ia.[1] 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.[4] International trade of phosphamidon is covered by the Rotterdam Convention.

References

  1. ↑ 1.0 1.1 1.2 Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 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. 
  3. ↑ 3.0 3.1 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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