Methiocarb

Methiocarb
Names
Preferred IUPAC name
3,5-Dimethyl-4-(methylsulfanyl)phenyl methylcarbamate
Other names
Mercaptodimethur
Mesurol
Identifiers
3D model (JSmol)
1881431
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.357 Edit this at Wikidata
EC Number
  • 217-991-2
KEGG
MeSH Methiocarb
UNII
  • InChI=1S/C11H15NO2S/c1-7-5-9(14-11(13)12-3)6-8(2)10(7)15-4/h5-6H,1-4H3,(H,12,13) checkY
    Key: YFBPRJGDJKVWAH-UHFFFAOYSA-N checkY
  • O=C(Oc1cc(c(SC)c(c1)C)C)NC
  • O=C(Oc1cc(c(SC)c(c1)C)C)NC
Properties
C11H15NO2S
Molar mass 225.312
Appearance Colourless crystals
Density 1.25 g cm−3
Melting point 118.5 °C (245.3 °F; 391.6 K)
Boiling point 311 °C (592 °F; 584 K) (degrades at 300 °C or 572 °F or 573 K)
0.027 g L−1
Solubility in Xylene 20 g L−1
Solubility in Acetone 144 g L−1
Solubility in Ethyl acetate 87 g L−1
Solubility in 1-Octanol 31 g L−1
log P 3.18
Vapor pressure .015 mPa
.12 mPa m3 mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Skin irritant, neurotoxin
Flash point Not highly flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Methiocarb is a carbamate pesticide (an acetylcholinesterase inhibitor) which is used as an insecticide,[1][2] bird repellent,[3] acaricide[2] and molluscicide[2] since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol[4] and mercaptodimethur.

Due to its toxicity, methiocarb approval as a plant protection product has been withdrawn by the EU effective 2020.[5]

  1. ^ "Interactive MoA Classification". IRAC (Insecticide Resistance Action Committee). 2021-11-15. Retrieved 2022-02-15.
  2. ^ a b c "Prevention, Pesticides And Toxic Substances: R.E.D. FACTS: Methiocarb" (PDF). United States Environmental Protection Agency (EPA). EPA. Retrieved 28 March 2013.
  3. ^ Bailey, PT; Smith, G (1 January 1979). "Methiocarb as a bird repellent on wine grapes". Australian Journal of Experimental Agriculture. 19 (97): 247. doi:10.1071/EA9790247.
  4. ^ Ozden, Sibel; Catalgol, Betul; Gezginci-Oktayoglu, Selda; Arda-Pirincci, Pelin; Bolkent, Sehnaz; Alpertunga, Buket (30 June 2009). "Methiocarb-induced oxidative damage following subacute exposure and the protective effects of vitamin E and taurine in rats". Food and Chemical Toxicology. 47 (7): 1676–1684. doi:10.1016/j.fct.2009.04.018. PMID 19394395.
  5. ^ "COMMISSION IMPLEMENTING REGULATION (EU) 2019/1606 of 27 September 2019". EUR-Lex. 2019-09-30. Retrieved 2021-07-08.

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