Abstract
Neonicotinoid insecticides act agonistically on insect nicotinic acetylcholine receptors (nAChRs). Like imidacloprid (IMI), all neonicotinoids bind with high affinity (I 50 -values ∼ 1 nM) to [ 3 H]IMI binding sites on insect nAChRs. One notable omission is thiamethoxam (THIAM), showing binding affinities up to 10,000-fold less potent than other neonicotinoids, using housefly head membrane preparations. Clothianidin (CLOTHI) exhibits high activity as an agonist on isolated neurons at concentrations as low as 30 nM. Pharmacokinetic studies in different insect species revealed that THIAM was rapidly metabolized to CLOTHI, which shows high affinity to nAChRs in both binding assays and whole cell voltage clamp studies. When applied to cotton plants, THIAM was also quickly metabolized, with CLOTHI being the predominant neonicotinoid in planta briefly after application, as indicated by LC-MS/MS analyses. Our studies show that THIAM is likely to be a neonicotinoid precursor for CLOTHI and not active by itself.
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