Phosphamidon
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| Names | |
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| IUPAC name
(E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
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| Other names
Dimecron
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.032.818 |
| KEGG | |
PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| 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): | |
LD50 (median dose)
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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).
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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
[edit]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
[edit]- ^ a b c Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
- ^ a b Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg. 2: P1153-1155.
- ^ 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.
- ^ S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Br. J. Ind. Med. 22: 236-239, 1965.