Carbaryl selective toxicity

The CBs used as pesticides are N-substituted esters of carbamic acid. CBs developed in the 1950s as insect repellents were found to have insecticidal activity, leading to the development of the napthyl CBs with high anti-ChE activity and selective toxicity against insects. One example is carbaryl it is widely used because of its low toxicity to mammals and its degradability. Aldicarb, a plant systemic, is more toxic than carbaryl. A few years ago aldicarb was associated with a July 4th holiday incident when West Coast residents complained of anticholinergic symptoms after eating aldicarb-contaminated watermelon. 

Figure 12.63 provides another example of the diversity of metabolic processes to which pesticides are subjected after application. In the case of the carbamate insecticide carbaryl, the predominant processes are oxidation and hydrolysis, which maybe followed by conjugation of primary metabolites with glutathione. The character of metabolic transformations is closely related to the pesticide selectivity (toxicity) to target and non-target organisms. 

Uncharged carbamates, such as carbaryl (8.20, sevin), can penetrate the CNS of insects (which do not use AChE in their neuromuscular junction) and they act quite selectively as insecticides with a low toxicity to mammals (median lethal dose [LDjg] in the rat = 540 mg/kg, p.o.). Many useful insecticides can thus be found in this group. Malathion (8.21) is a pro-drug, since the thiophosphate must be bioactivated to the phosphate form—a transformation carried out by insects but not mammals. Additionally, the ester groups of malathion are rapidly hydrolyzed in higher organisms to water-soluble and... 

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