Phosphamidon

Not to be confused with phosphoramidon.

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

Phosphamidon

Names
IUPAC name (E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
Other names Apamidon Dimecron Dixon Famfos Merkon Sundaram 1975
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
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H311, H341, H410
Precautionary statements	P203, P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P318, P321, P330, P361+P364, P391, P405, P501
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

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.