Mevinphos

Mevinphos
Names
IUPAC name
2-methoxycarbonyl-1-methylvinyl dimethyl phosphate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.177
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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Infobox references

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][7] 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.[8]

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. ^ Raman, P. (2014). Wexler, Philip (ed.). "Mevinphos". Encyclopedia of Toxicology (Third Edition). Academic Press: 332–335. doi:10.1016/B978-0-12-386454-3.00335-3. ISBN 9780123864550. Retrieved 15 August 2025.
  5. ^ Hartwig, Andrea; Arand, Michael (2024). "Mevinphos". The MAK Collection for Occupational Health and Safety (in German). 9 (3). German Medical Science. doi:10.5167/uzh-269711. ISSN 2509-2383. Retrieved 15 August 2025.
  6. ^ "Transitioning the Legal Establishment of Maximum Residue Limits (MRLs) for Pesticides From the Food and Drugs Act to the Pest Control Products Act" (PDF). Pest Management Regulatory Agency. Ottawa, Ontario: Health Canada. 9 July 2008. Retrieved 15 August 2025.
  7. ^ "Consolidated List of Banned Pesticides (CL)" (Microsoft Excel). Pesticide Action Network (PAN). PAN International. July 2015. Retrieved 15 August 2025.
  8. ^ "Mevinphos" (PDF). EPA R.E.D. Facts. Washington, DC: United States Environmental Protection Agency. September 1994. pp. 4–5. Retrieved 15 August 2025.

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)
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