Mevinphos

Last updated
Mevinphos
Mevinphos E,Z Isomers Formulae V.1.svg
Names
IUPAC name
2-methoxycarbonyl-1-methylvinyl dimethyl phosphate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.177 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3 X mark.svgN
    Key: GEPDYQSQVLXLEU-UHFFFAOYSA-N X mark.svgN
  • 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
AppearanceColorless 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 an organophosphate insecticide that acts as an acetylcholinesterase inhibitor to control insects in a wide range of crops. It is 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]

Contents

Manufacture

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

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References

  1. 1 2 Muller, Franz, ed. (2000). Agrochemicals: Composition, Production, Toxicology, Applications. Toronto: Wiley-VCH. ISBN   3-527-29852-5.
  2. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0503". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "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