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
CAS Number	13171-21-6  Y 297-99-4 (E) Y 23783-98-4 (Z) Y
3D model (JSmol)	Interactive image
ChemSpider	23990  N
ECHA InfoCard	100.032.818
KEGG	C18689  Y
PubChem CID	25750
UNII	7H857A6N6H  Y 54VR7A0BQD  (E) Y HQ7958Q90Z  (Z) Y
CompTox Dashboard (EPA)	DTXSID7021156
InChI 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
SMILES CCN(CC)C(=O)/C(=C(\C)/OP(=O)(OC)OC)/Cl
Properties
Chemical formula	C10H19ClNO5P
Molar mass	299.69 g·mol−1
Density	1.2132 g/cm3 [1]
Boiling point	162 °C (324 °F; 435 K) (1.5 mmHg) [2]
Solubility in water	Miscible
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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  YN ?) Infobox references

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. Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
2. Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg. 2: P1153-1155.
3. 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.