Aldicarb

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. Aldicarb is considered "extremely hazardous" by the EPA and World Health Organization and has been banned in more than 100 countries. In case of severe poisoning, the victim dies of respiratory failure.

Aldicarb
Names
IUPAC name
2-Methyl-2-(methylthio)propanal O-(N-methylcarbamoyl)oxime
Other names
Temik
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.749
EC Number
  • 204-123-2
KEGG
PubChem CID
RTECS number
  • UE2275000
UNII
  • InChI=1S/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5+ Y
    Key: QGLZXHRNAYXIBU-WEVVVXLNSA-N Y
  • InChI=1/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5+
    Key: QGLZXHRNAYXIBU-WEVVVXLNBS
SMILES
  • CNC(=O)O/N=C/C(C)(C)SC
Properties
C7H14N2O2S
Molar mass 190.26 g·mol−1
Appearance colorless crystals
Odor faint sulfur odor
Density 1.195 g/cm2
Melting point 99.5 °C (211.1 °F; 372.6 K)
Boiling point 251 °C (484 °F; 524 K)
0.573 g/100 mL
Solubility soluble in acetone, benzene, chlorobenzene, diethyl ether, isopropyl alcohol, methylene chloride, toluene
slightly soluble in xylene
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 0.84 mg/kg (oral, rats)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Aldicarb was first synthesized in 1965 by Payne and Weiden, and was sold on the market for the first time in 1970. The synthesis of aldicarb results in both the E and Z isomers.

Aldicarb is effective where resistance to organophosphate insecticides has developed, and is extremely important in potato production, where it is used for the control of soil-borne nematodes and some foliar pests. Its high level of solubility restricts its use in certain areas where the water table is close to the surface.

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