Methomyl

Source: Wikipedia, the free encyclopedia.
Methomyl[1]
Skeletal formula of (E)-Methomyl
(E)-Methomyl
Space-filling model of (E)-Methomyl
Skeletal formula of (Z)-Methomyl
(Z)-Methomyl
Space-filling model of (E)-Methomyl
Names
IUPAC name
(E,Z)-methyl N-{[(methylamino)carbonyl]oxy}ethanimidothioate
Other names
Lannate, Mesomile, Methomex, Nudrin
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.037.089 Edit this at Wikidata
  • InChI=1S/C5H10N2O2S/c1-4(10-3)7-9-5(8)6-2/h1-3H3,(H,6,8) ☒N
    Key: UHXUZOCRWCRNSJ-UHFFFAOYSA-N ☒N
  • InChI=1/C5H10N2O2S/c1-4(10-3)7-9-5(8)6-2/h1-3H3,(H,6,8)
    Key: UHXUZOCRWCRNSJ-UHFFFAOYAU
  • CNC(=O)ON=C(C)SC
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 their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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);

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

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.

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

  1. ^ Merck Index, 11th Edition, 5905
  2. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0387". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Methomyl at Extension Toxicology Network
  4. ^ "EU pesticides database".
  5. ^ Conservation Warden Warns: Fly bait to control wild animals – illegal and a bad idea (Wisconsin Department of Natural Resources)
  6. ^ "Farm stores promoted poisoning raccoons, state chemist says". Archived from the original on 2015-09-24. Retrieved 2012-08-09.
  7. ^ a b c d e EPA R.E.D. FACTS - Methomyl (PDF) (Technical report). U. S. Environmental Protection Agency. December 1998. EPA-738-F-98-019.
  8. PMID 22892654
    .
  9. doi:10.1016/j.pestbp.2009.09.003
    .
  10. ^ Howard, P. H. (1991). Handbook of Environmental Fate and Exposure Data for Organic Chemicals: Pesticides. Chelsea, MI: Lewis Publishers. pp. 3–15.
  11. ^ a b c "Extoxnet Pip - Methomyl".

External links

  • Methomyl in the Pesticide Properties DataBase (PPDB)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Methomyl&oldid=1220222675"