The exploration of chiral N -cyano sulfiliminyl dicarboxamides on insecticidal activities

Due to new mechanism of action and ecofriendly characteristics, dicarboxamide insecticides have attracted more and more attentions in modern pest management. A series of 20 dual chiral N-cyano sulfilimines containing two centers (carbon and sulfur) were designed and synthesized. All title compounds were determined by 1H NMR, high-resolution mass spectrometry (HRMS) and optical polarimeter. The preliminary results indicated that some of them exhibited favourable insecticidal activities against oriental armyworm (Pseudaletia separata Walker). These isomers exhibited different impact on activity following the sequence as (Sc, Ss) ≥ (Sc, Rs), and the rule of title compounds’ activity against oriental armyworm was 3-CF3 ≥ 2 CH3 4 Cl >2, 3, 4-trifluro in the anilide moiety. The results indicated that these groups such as 3-CF3, 2 CH3 4 Cl or 2, 3, 4-trifluro were inefficient to replace heptafluoroisopropyl group for high larvicidal activity, which provided some guidance for the further modifications of sulfiliminyl dicarboxamides.