{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424730608 | Name = Mevinphos | ImageFile =Mevinphos E,Z Isomers Formulae V.1.svg | ImageSize = | IUPACName = 2-methoxycarbonyl-1-methylvinyl dimethyl phosphate | SystematicName = | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | CASNo = 7786-34-7 | CASNo_Comment = | CASNo_Ref = {{cascite|correct|??}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 14ZYO4IKXT | PubChem = 9560 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 9185 | InChI = 1/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3 | InChIKey = GEPDYQSQVLXLEU-UHFFFAOYAN | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = GEPDYQSQVLXLEU-UHFFFAOYSA-N | EINECS = | SMILES =CC(=CC(=O)OC)OP(=O)(OC)OC | Beilstein = | Gmelin = | 3DMet =}} |Section2={{Chembox Properties | C=7 | H=13 | O=6 | P=1 | Appearance = Colorless liquid<ref name=agrochem>{{cite book|editor=Muller, Franz|title=Agrochemicals: Composition, Production, Toxicology, Applications|year=2000|publisher=Wiley-VCH|location=Toronto|isbn=3-527-29852-5}}</ref> | Density = 1.25 g/mL<ref name=PGCH/> | MeltingPtC = 21 | MeltingPt_notes = (''E'' isomer); 6.9 °C (''Z'' isomer) | BoilingPtC = | BoilingPt_notes = | pKa = | pKb = | Solubility = miscible<ref name=PGCH/> | VaporPressure = 0.003 mmHg (20°C)<ref name=PGCH/> }} |Section3={{Chembox Structure | CrystalStruct = | Coordination = | MolShape = }} |Section4={{Chembox Thermochemistry }} |Section5={{Chembox Pharmacology | AdminRoutes = | Bioavail = | Metabolism = | HalfLife = | ProteinBound = | Excretion = | Legal_status = | Legal_US = | Legal_UK = | Legal_AU = | Legal_CA = | PregCat = | PregCat_AU = | PregCat_US = }} |Section6={{Chembox Explosive | ShockSens = | FrictionSens = | DetonationV = | REFactor = }} |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPtF = 347 | FlashPt_ref = <ref name=PGCH/> | AutoignitionPt = | ExploLimits = | PEL = TWA 0.1 mg/m<sup>3</sup> [skin]<ref name=PGCH>{{PGCH|0503}}</ref> | IDLH = 4 ppm<ref name=PGCH/> | LC50 = 14 ppm (rat, 1 hr)<ref name=IDLH>{{IDLH|7786347|Phosdrin}}</ref> | LD50 = 3 mg/kg (rat, oral)<br/>4 mg/kg (mouse, oral)<br/>6-7 mg/kg (rat, oral)<ref name=IDLH/> | REL = TWA 0.01 ppm (0.1 mg/m<sup>3</sup>) ST 0.03 ppm (0.3 mg/m<sup>3</sup>) [skin]<ref name=PGCH/> }} |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = }} }}
'''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.<ref name="Uses">{{cite book |last1=Raman |first1=P. |title=Encyclopedia of Toxicology |chapter=Mevinphos |date=2014 |pages=332–335 |doi=10.1016/B978-0-12-386454-3.00335-3 |isbn=978-0-12-386455-0 }}</ref> 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.<ref name="EU status">{{cite journal |last1=Hartwig |first1=Andrea |author2=MAK Commission |last3=Arand |first3=Michael |title=Mevinphos |journal=The MAK Collection for Occupational Health and Safety |volume=9 |issue=3 |date=2024 |article-number=Doc053 |doi=10.5167/uzh-269711 }}</ref> Nor is it approved for use in Canada.<ref>{{cite web |title=Transitioning the Legal Establishment of Maximum Residue Limits (MRLs) for Pesticides From the Food and Drugs Act to the Pest Control Products Act |url=https://publications.gc.ca/collections/collection_2008/pmra-arla/H113-29-2008-2E.pdf |website=Pest Management Regulatory Agency |publisher=Health Canada |access-date=15 August 2025 |location=Ottawa, Ontario |date=9 July 2008}}</ref> 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.<ref name="US ban">{{cite web |title=Mevinphos |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-015801_1-Sep-94.pdf |website=EPA R.E.D. Facts |publisher=United States Environmental Protection Agency |access-date=15 August 2025 |location=Washington, DC |pages=4–5 |date=September 1994}}</ref>
==Manufacture== Mevinphos is produced by the reaction of trimethyl phosphite with chloroacetoacetate.<ref name=agrochem />
==References== {{reflist}}
==Further reading== * {{cite book|editor=Wolverton, B.C.|title=Aquatic Plants for Removal of Mevinphos from the Aquatic Environment; Volume 72720 of NASA Technical memorandum|year=1975|publisher=National Space Technology Laboratories (U.S.)|location=Mississippi}}
==External links == * {{PPDB|471}}
{{Insecticides}} {{Acetylcholine metabolism and transport modulators}}
Category:Acetylcholinesterase inhibitors Category:Neurotoxins Category:Insecticides Category:Organophosphate insecticides Category:Carboxylate esters Category:Organophosphates Category:Alkene derivatives Category:Acetoacetate esters