Methomyl
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| Molar mass | 162.20 |
| Appearance | White crystalline solid[2] |
| Odor | Slight, sulfur-like[2] |
| Density | 1.2946 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Vapor pressure | 0.00005 mmHg (25°C)[2] |
| Flash point | Template:Chembox CalcTemperatures |
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Methomyl is a carbamate insecticide 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]
Use
Methomyl is a broad-spectrum insecticide that is used to kill insect pests.[7] Methomyl is registered for commercial/professional use under certain conditions on sites including field, vegetable, and orchard crops; turf (sod farms 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 for homeowner or non-professional application.[7] However, Heliothis virescens developed a resistance to methomyl within 5 years.[8] Other species like Helicoverpa assulta also developed resistance after exposure.[9]
Toxicity
In acute toxicity testing, methomyl is placed in EPA Toxicity Category I (the highest toxicity category out of four) via the oral route and in eye irritation studies.[7] It is in lower Toxicity Categories for inhalation (Category II), acute dermal effects (Category III), and acute skin irritation (Category IV). Methomyl is not likely to be a carcinogen (EPA carcinogen Category E).[7]
Ecotoxicity
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 estimated aqueous half-life for the insecticide is 6 days in surface water and over 25 weeks in groundwater.[11]
Synthesis
First prepare thioester:
Second prepare oxime from thioester:
Third prepare product from methyl isocyanate and the finished oxime:
Trade names
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]
References
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- ↑ Merck Index, 11th Edition, 5905
- ↑ a b c d e f g Script error: No such module "citation/CS1".
- ↑ Methomyl at Extension Toxicology Network
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- ↑ Conservation Warden Warns: Fly bait to control wild animals – illegal and a bad idea (Wisconsin Department of Natural Resources)
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External links
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