222. Aldicarb

Nomenclature

CAS number: 116-06-3
2-Methyl-2-(methylthio)propanal O-[(methylamino)carbonyl]oxime; 2-methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime; UC-21149; Temik (Bayer CropSci.).
C7H14N2O2S; mol wt 190.26.
C 44.19%, H 7.42%, N 14.72%, O 16.82%, S 16.85%.

Description and references

Acetylcholinesterase inhibitor. Prepn: L. K. Payne, Jr., M. H. J. Weiden, FR 1377474; eidem, US 3217037 (1963, 1965 both to Union Carbide); L. K. Payne, Jr. et al., J. Agric. Food Chem. 14, 356 (1966). Metabolism: W. J. Bartley et al., ibid. 18, 446 (1970). Crystal and molecular structure: F. Takusagawa, R. A. Jacobson, ibid. 25, 333 (1977). HPLC-APCI-MS determn in fruits and vegetables: G. S. Nunes et al., J. Chromatogr. A 888, 113 (2000). Efficacy for control of nematodes on potato: S. L. Hafez et al., Nematol. Mediterranea 30, 227 (2002); of thrips on cotton: K. H. Lohmeyer et al., J. Econ. Entomol. 96, 748 (2003). Efficacy on citrus and economic analysis: L. Blakeley et al., HortTechnology 13, 694 (2003). Review: R. R. Romine, Anal. Methods Pestic. Plant Growth Regul. 7, 147-162 (1973). Review of persistence in soil and root crops: A. C. Maheshwari, V. S. Kavadia, Pesticides 19, 30-31 (1985); of groundwater contamination: H. A. Moye, C. J. Miles, Rev. Environ. Contam. Toxicol. 105, 99-146 (1988). Review of toxicology: R. L. Baron, T. L. Merriam, ibid. 105, 1-70 (1988); idem, Environ. Health Perspect. 102, Suppl. 11, 23-27 (1994).

Chemical structure

Properties

Crystals from isopropyl ether, mp 99-100° with dec >100°. d425 1.195. Vapor pressure (25°): 1×104 mmHg. Sparingly sol in water and certain organic solvents, most sol in chloroform and acetone. Percent soly: acetone 28 (10°), 43 (30°), 50 (50°); benzene 9 (10°), 24 (30°), 49 (50°); carbon tetrachloride 2 (10°), 5 (30°), 25 (50°); chloroform 38 (10°), 44 (30°), 50 (50°); methyl isobutyl ketone 13 (10°), 24 (30°), 42 (50°); toluene 10 (10°), 12 (30°), 33 (50°); water 0.4 (10°), 0.9 (30°), 1.4 (50°). LD50 in male and female rats (mg/kg): 0.81-0.93, 0.67-1.20 orally. LC50 (96 hr) in rainbow trout, bluegill sunfish (ppb): 560-580, 50-100 (Baron, 1988).

Use

Insecticide, acaricide, nematocide.