Structure-activity relationship of alkanols as mosquito larvicides with novel findings regarding their mode of action.
Primary alcohols, from methanol to eicosanol, were applied to water for control of larval stage mosquitoes. By applying the alkanols as soluble solutions rather than as insoluble monolayers, and by trapping larvae under glass in assays that isolated them from the surface phenomena believed to be responsible for death by suffocation, we have shown that the action of alkanols against mosquito larvae is biochemical in nature, not just physical. Primary alcohols are known to act as general anesthetics, with increasing potency correlated to increasing chain length until a point of cutoff is reached, usually at dodecanol (C12), after which activity disappears entirely. In mosquitoes, we found that activity levels off after undecanol (C11) but does not disappear until after pentadecanol (C15), that it is reversible, and that chain length plays a role not only in potency, but also in the time needed to manifest toxic effects. We used sonication, a surfactant, temperature, and the introduction of double bonds to manipulate activity around the cutoff, suggesting that it is at least partially a function of solubility. Mosquitoes appear to be the first animal for which cutoff has been demonstrated to occur at a chain length beyond C12, offering new insights into the molecular basis of anesthetic cutoff and suggesting the possibility that alkanols might be used for selective pest control. Alkanols are stable, colorless, inexpensive, biodegradable and essentially non-toxic to humans, making them promising candidates for pest management programs.
Hammond
D G
DG
Agricultural and Environmental Chemistry Group, University of California at Berkeley, 94720-3112, USA.
Kubo
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I
D000438:Alcohols / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D001237:Asphyxia; D002244:Carbon / Q000737:chemistry; D009033:Culicidae / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D007814:Larva / Q000187:drug effects*; D007928:Lethal Dose 50; D009032:Mosquito Control; D013329:Structure-Activity Relationship; D013500:Surface Tension
D000438:Alcohols; D002244:Carbon