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Mevinphos

From Wikipedia, the free encyclopedia
Mevinphos
Names
IUPAC name
2-methoxycarbonyl-1-methylvinyl dimethyl phosphate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.029.177Edit 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 mass224.149 g·mol−1
AppearanceColorless liquid[1]
Density1.25 g/mL[2]
Melting point21 °C (70 °F; 294 K) (E isomer); 6.9 °C (Z isomer)
miscible[2]
Vapor pressure0.003 mmHg (20°C)[2]
Hazards
Flash point175 °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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Mevinphos is a toxicorganophosphateinsecticide that acts as anacetylcholinesterase inhibitor to control insects in a wide range of crops. It was most commonly used for the control of chewing and sucking insects likeaphids,grasshoppers,cutworms,leafhoppers, andcaterpillars, as well asspider mites andticks.[4] Common synonym names are duraphos, fosdrin, menite, mevinfos, mevinox, phosdrin, and phosdrine. While there is no specific ban in theEU, it is not approved for use in any member nations.[5] Nor is it approved for use inCanada.[6] TheEPA issued a Cancellation Order for all Mevinphos registrations on June 30, 1994, effectively banning its manufacture and use in theUnited States, all manufacture ceased shortly after, and its use was officially banned after February 28, 1995.[7]

Manufacture

[edit]

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

References

[edit]
  1. ^abMuller, Franz, ed. (2000).Agrochemicals: Composition, Production, Toxicology, Applications. Toronto: Wiley-VCH.ISBN 3-527-29852-5.
  2. ^abcdefgNIOSH Pocket Guide to Chemical Hazards."#0503".National Institute for Occupational Safety and Health (NIOSH).
  3. ^ab"Phosdrin".Immediately Dangerous to Life or Health Concentrations.National Institute for Occupational Safety and Health.
  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. Retrieved15 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. Retrieved15 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. Retrieved15 August 2025.
  7. ^"Mevinphos"(PDF).EPA R.E.D. Facts. Washington, DC:United States Environmental Protection Agency. September 1994. pp. 4–5. Retrieved15 August 2025.

Further reading

[edit]
  • 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.).

External links

[edit]
  • Mevinphos in the Pesticide Properties DataBase (PPDB)
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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