Phosphamidon
Not to be confused with phosphoramidon.
-Phosphamidon_Structural_Formulae_V.1.svg.png) | |
| Names | |
|---|---|
| IUPAC name
(E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate | |
| Other names
Dimecron | |
| Identifiers | |
13171-21-6  297-99-4 (E)  23783-98-4 (Z) | |
| ChemSpider | 23990 |
| |
| Jmol-3D images | Image |
| KEGG | C18689 |
| PubChem | 25750 |
| |
| UNII | 7H857A6N6H |
| Properties | |
| Molecular formula |
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 | |
| LD50 (Median lethal dose) |
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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
- ↑ 1.0 1.1 1.2 Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 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.
- ↑ 3.0 3.1 Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg 2: P1153–1155.
- ↑ S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Brit. J. Ind. Med. 22: 236-239, 1965.