Aminocarb

History

Aminocarb has been extensively used in eastern Canada since 1976 in order to control the spruce budworm. The fate of this chemical in the ecosystem and detection of aminocarb was studied by the use of two-dimensional thin-layer chromatography. The use of thin-layer chromatography helped isolate and identify the methyl amino, amino and hydroxymethyl analogues from the in vitro metabolism of aminocarb by liver homogenates from humans and rats.

Production and uses

Aminocarb is a carbamate insecticide widely used to protect cotton fields, crop fields, and forests from insect infestation. It helps in the control of aphids, soil mollusks, lepidopterous larvae, and other types of chewing insects. It is most commonly administered as an aerosol spray.

Reactions

Aminocarb can be degraded through irradiation and hydrolysis.

Irradiation

Aminocarb can be broken down by short-wave ultraviolet radiation. Irradiation is often carried out by a high pressure xenon-mercury lamp. Irradiating aminocarb in ethyl alcohol and cyclohexene solutions initially causes the oxidation of the dimethylamine moiety. The process eventually leads to the formation of a 4-dimethylamino-3-methyl phenol product.

Hydrolysis

Aminocarb undergoes hydrolysis to 4-dimethylamino-3-methylphenol in 25 °C purified water when pH of the water is 6.4. 4-dimethylamino-3-methylphenol is then either directly or via 2-methyl-1,4-dihydorquinone converted to 2-methyl-1,4-benzoquinone. If methylamine or diethylamine are present in the solution 2-methyl-1,4-benzoquinone will readily react. Monoepoxides and diepoxides of 2-methyl-1,4-benzoquinone are formed.

Biomedical effects

In an experiment where young brown bullhead were exposed to aminocarb at lethal and sublethal concentrations, their tissue distribution was examined and showed that the concentration of residues in each tissue increased with the concentration of exposure of aminocarb. The liver and stomach/intestine had the highest amount of accumulation of residues.

Aminocarb is also known as a cholinesterase inhibitor that has nervous system effects causing convulsions and respiratory failure. It can also be absorbed through the skin, causing long-term effects to the nervous system and liver.

References

References

1. "Aminocarb safety and hazards".
2. (1993). "Agrochemicals Desk Reference: Environmental Data". CRC Press.
3. (1980). "Detection of aminocarb and its major metabolites by thin-layer chromatography". Journal of Chromatography A.
4. (1987). "Role of Formulation Ingredients and Physical Properties on Droplet Size Spectra, Deposition, and Persistence of Aerially Sprayed Aminocrab and Mexacarbate in Forest Litter and Soil Samples". Pesticide Formulations and Application Systems.
5. (2010). "Handbook of Chemicals and Safety". CRC Press.
6. (December 2012). "FAO plant production and protection papers". Food and Agriculture Organization of the United Nations.
7. (1999-10-28). "Agrochemical and Pesticide Desk Reference on CD-ROM". CRC Press.
8. (December 2012). "Agrochemical and Pesticide Desk Reference on CD-ROM: Crcnetbase". CRC Press }}{{page needed.
9. (2001). "Metabolic Maps".
10. (1986). "Tissue distribution of ¹⁴C-labeled residues of aminocarb in brown bullhead (''Ictalurus nebulosus'' Le Sueur) following acute exposure". Ecotoxicology and Environmental Safety.
11. "Aminocarb". U.S. National Library of Medicine.