Synthesis and structure-activity relationships of dinotefuran derivatives: Modification in the tetrahydro-3-furylmethyl part

Abstract

The (±)-tetrahydro-3-furylmethyl moiety, which is a characteristic part of the novel neonicotinoid dinotefuran, was found by research in which acetylcholine was selected as the lead compound. SAR (structure-activity relationships) for the tetrahydrofuran part indicated that the non-substituted moiety showed the highest level of activity, 4- and 5-substituted moieties showed intermediate levels, and 2- and 3-substituted moieties lost the activity. Conformational analysis of these compounds indicated that the substituents changed little the hypothetical active conformation of dinotefuran. Computational analysis proved that dinotefuran, a methoxypropyl compound and other neonicotinoids well overlapped, and dinotefuran adopts the active conformation more easily than the methoxypropyl compound. © Pesticide Science Society of Japan.