Phosphamidon

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.818 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3 ☒N
    Key: RGCLLPNLLBQHPF-UHFFFAOYSA-N ☒N
  • InChI=1/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3
    Key: RGCLLPNLLBQHPF-UHFFFAOYAA
  • CCN(CC)C(=O)/C(=C(\C)/OP(=O)(OC)OC)/Cl
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)[3]
Boiling point 162 °C (324 °F; 435 K) (1.5 mmHg)[2]
Miscible
Hazards
Lethal dose or concentration (LD, LC):
13 mg/kg (mouse, oral)[3]
6 mg/kg (mouse, IV)[3]
20 mg/kg (rat, oral)[3]
26 mg/kg (rat, subcut.)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Phosphamidon is an organophosphate insecticide first reported in 1960.[3][2] 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. ^ a b c Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
  2. ^ a b Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg. 2: P1153-1155.
  3. ^ a b c d e f 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. doi:10.1007/BF02226232. S2CID 6714997.
  4. ^ S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Br. J. Ind. Med. 22: 236-239, 1965.
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