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| Names | |||
|---|---|---|---|
| IUPAC name (E,Z)-methylN-{[(methylamino)carbonyl]oxy}ethanimidothioate | |||
| Other names Lannate, Mesomile, Methomex, Nudrin | |||
| Identifiers | |||
3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.037.089 | ||
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| Properties | |||
| C5H10N2O2S | |||
| Molar mass | 162.20 | ||
| Appearance | White crystalline solid[2] | ||
| Odor | Slight, sulfur-like[2] | ||
| Density | 1.2946 g/cm3 | ||
| Melting point | 78 to 79 °C (172 to 174 °F; 351 to 352 K) | ||
| 58 g/L | |||
| Vapor pressure | 0.00005 mmHg (25°C)[2] | ||
| Hazards | |||
| Flash point | Noncombustible[2] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | none[2] | ||
REL (Recommended) | TWA 2.5 mg/m3[2] | ||
IDLH (Immediate danger) | N.D.[2] | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Methomyl is acarbamateinsecticide introduced in 1966. It is highly toxic to humans, livestock, pets, and wildlife.[3]The EU imposed a pesticide residue limit of 0,01 mg/kg for all fruit and vegetables.[4]
Methomyl is a common active ingredient in commercial fly bait, for which the label instructions in the United States warn that "It is a violation of Federal Law to use this product in a manner inconsistent with its labeling." "Off-label" uses and other uses not specifically targeted at problem insects are illegal, dangerous, and ill-advised.[5][6]
Methomyl is a broad-spectrum insecticide that is used to killinsect pests.[7] Methomyl is registered for commercial/professional use under certain conditions on sites including field, vegetable, and orchard crops; turf (sodfarms only);livestock quarters; commercial premises; and refuse containers. Products containing 1% Methomyl are available to the general public for retail sale, but more potent formulations are classified as restricted-use pesticides: not registered forhomeowner or non-professional application.[7] However,Heliothis virescens developed a resistance to methomyl within 5 years.[8] Other species likeHelicoverpa assulta also developed resistance after exposure.[9]
In acute toxicity testing, methomyl is placed inEPAToxicity Category I (the highest toxicity category out of four) via theoral route and in eye irritation studies.[7] It is in lower Toxicity Categories for inhalation (Category II), acutedermal effects (Category III), and acute skin irritation (Category IV). Methomyl is not likely to be acarcinogen (EPA carcinogen Category E).[7]
Methomyl has low persistence in the soil environment, with a reported half-life of approximately 14 days.[10] Because of its high solubility in water, and low affinity for soil binding methomyl may have potential for groundwater contamination.[7][11] The estimatedaqueoushalf-life for the insecticide is 6 days in surface water and over 25 weeks ingroundwater.[11]
First prepare thioester:
Second prepareoxime from thioester:
Third prepare product frommethyl isocyanate and the finished oxime:
Common names for methomyl include metomil and mesomile. Trade names include Acinate, Agrinate, DuPont 1179, Flytek, Kipsin, Lannate, Lanox, Memilene, Methavin, Methomex, Nudrin, NuBait, Pillarmate and SD 14999[11]
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-Methomyl_molecule_spacefill.png)
-Methomyl_formula_structural.svg)
-Methomyl_molecule_spacefill.png)
