Investigation of new structural scaffolds is one of the approaches in the discovery of new insect controlling agents. The new optically active and geometric scaffolds of dicarboxamides containing N-cyano and N-trifluoroacetyl sulfiliminyl moieties were designed, synthesized and evaluated against oriental armyworm (Pseudaletiaseparata Walker) and diamondback moth (Plutellayylostella L.). Our bioassay indicated that most of the title compounds exhibited significant insecticidal activities. The structure activity relationship study indicated that these new optically active and geometric N-cyano and N-trifluoroacetyl sulfilimines were important for high activity, among which six title compounds reached the potency level of Flubendiamide. It was worth noting that LC50Values of three compounds were 0.0504, 0.0699 and 0.1374, lower than that of Flubendiamide (0.1412). It was obviously observed that (Sc, Rs) and (Sc, Ss) isomers exhibited higher insecticidal activities than the enantiomers (Rc, Ss) and (Rc, Rs). In comparison to chiral center of sulfur, the chiral carbon influences greater. Among the four series, Ss configurations exhibited better activities than Rs counterparts. Thus synergism is suggested to be involved. Most compounds possessed excellent activities against diamondback moth. In particular, four title compounds gave higher activity than Flubendiamide, two of which showed a death rate of 70% and 20% at 10-7 mg L-1 (flubendiamide 50% at 10-3 mg L-1). Most N-trifluoroacetyl sulfilimines showed higher activities than corresponding N-cyano sulfilimines, probably due to better solubility and hydrophobic properties. CoMFA calculations indicated that the chiral and geometric scaffolds containing strong electron-withdrawing group as CN, COCF3 are important to attain their high potency. The present work demonstrated that new optically active and geometric scaffolds for dicarboxamides containing N-cyano or N-trifluoroacetyl sulfiliminyl moieties could be considered as a starting point to discover new insect ryanodine receptor modulators.

Asymmetric synthesis of new geometric scaffolds for dicarboxamides as potential ryanodine receptor inhibitors

248th National Meeting (2014)

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