Phosphamidon

Not to be confused with phosphoramidon.
Phosphamidon
Names
IUPAC name
(E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
Other names
Dimecron
Identifiers
13171-21-6 YesY
297-99-4 (E) N
23783-98-4 (Z) N
ChemSpider 23990 N
Jmol interactive 3D Image
KEGG C18689 YesY
PubChem 25750
UNII 7H857A6N6H YesY
Properties
C10H19ClNO5P
Molar mass 299.69 g·mol−1
Density 1.2132 g/cm3[1]
Melting point 120 to 123 °C (248 to 253 °F; 393 to 396 K)[2]
Boiling point 162 °C (324 °F; 435 K) (1.5 mmHg)[3]
Miscible
Hazards
Lethal dose or concentration (LD, LC):
13 mg/kg (mouse, oral)[2]
6 mg/kg (mouse, IV)[2]
20 mg/kg (rat, oral)[2]
26 mg/kg (rat, subcut.)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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 2 3 Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
  2. 1 2 3 4 5 6 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 für Toxikologie 18: 316–330.
  3. 1 2 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.
This article is issued from Wikipedia - version of the Sunday, February 14, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.