Mevinphos

Mevinphos
Names
IUPAC name
2-methoxycarbonyl-1-methylvinyl dimethyl phosphate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.177 Edit this at Wikidata
UNII
  • InChI=1S/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3 ☒N
    Key: GEPDYQSQVLXLEU-UHFFFAOYSA-N ☒N
  • InChI=1/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3
    Key: GEPDYQSQVLXLEU-UHFFFAOYAN
  • CC(=CC(=O)OC)OP(=O)(OC)OC
Properties
C7H13O6P
Molar mass 224.149 g·mol−1
Appearance Colorless liquid[1]
Density 1.25 g/mL[2]
Melting point 21 °C (70 °F; 294 K) (E isomer); 6.9 °C (Z isomer)
miscible[2]
Vapor pressure 0.003 mmHg (20°C)[2]
Hazards
Flash point 175 °C; 347 °F; 448 K[2]
Lethal dose or concentration (LD, LC):
3 mg/kg (rat, oral)
4 mg/kg (mouse, oral)
6-7 mg/kg (rat, oral)[3]
14 ppm (rat, 1 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.1 mg/m3 [skin][2]
REL (Recommended)
 TWA 0.01 ppm (0.1 mg/m3) ST 0.03 ppm (0.3 mg/m3) [skin][2]
IDLH (Immediate danger)
 4 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mevinphos is a toxic organophosphate insecticide that acts as an acetylcholinesterase inhibitor to control insects in a wide range of crops. It was most commonly used for the control of chewing and sucking insects, as well as spider mites. Common synonym names are duraphos, fosdrin, menite, mevinfos, mevinox, phosdrin, and phosdrine. It is not allowed in the EU anymore.[4]

Manufacture

Mevinphos is produced by the reaction of trimethyl phosphite with chloroacetoacetate.[1]

References

  1. ^ a b Muller, Franz, ed. (2000). Agrochemicals: Composition, Production, Toxicology, Applications. Toronto: Wiley-VCH. ISBN 3-527-29852-5.
  2. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0503". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "Phosdrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Mevinphos in the Pesticide Properties DataBase (PPDB)

Further reading

  • Wolverton, B.C., ed. (1975). Aquatic Plants for Removal of Mevinphos from the Aquatic Environment; Volume 72720 of NASA Technical memorandum. Mississippi: National Space Technology Laboratories (U.S.).
  • Mevinphos in the Pesticide Properties DataBase (PPDB)