Phosphamidon

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Phosphamidon
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Names
IUPAC name
(E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
Other names
Dimecron
Identifiers
3D model (JSmol)
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KEGG
UNII
Properties
C10H19ClNO5P
Molar mass 299.69 g·mol−1
Density 1.2132 g/cm3[1]
Melting point
Boiling point
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.[4] 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. 2.0 2.1 2.2 2.3 2.4 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. 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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