Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part

Dinotefuran ((RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine) is a new neonicotinoid which has a characteristic (±)-tetrahydro-3-furylmethyl moiety instead of the pyridine-like moiety of other neonicotinoids. A series of dinotefuran derivatives were synthesized and tested against hemiptera. SAR (structure-activity relationships) of the nitroguanidine part of dinotefuran are summarized as follows: (1) the mono-methyl group as a N-substituent gave the best activity for the acyclic nitroimino and nitromethylene compounds, (2) the acyclic compounds showed the same activity as the cyclic compounds against Nephotettix cincticeps and were superior to them against Laodelphax striatellus, (3) N-acylation of this series scarcely changed the level of activity. On the basis of these results, we selected dinotefuran for development. © Pesticide Science Society of Japan