Mevinphos

Chemical compound From Wikipedia, the free encyclopedia

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 like aphids, grasshoppers, cutworms, leafhoppers, and caterpillars, as well as spider mites and ticks.[4] Common synonym names are duraphos, fosdrin, menite, mevinfos, mevinox, phosdrin, and phosdrine. While there is no specific ban in the EU, it is not approved for use in any member nations.[5] Nor is it approved for use in Canada.[6] The EPA issued a Cancellation Order for all Mevinphos registrations on June 30, 1994, effectively banning its manufacture and use in the United States, all manufacture ceased shortly after, and its use was officially banned after February 28, 1995.[7]

Quick facts Names, Identifiers ...
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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Manufacture

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

References

Further reading

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