Design, Synthesis, Biological Evaluation and SARs of Novel Anthranilic Diamides Derivatives Containing Amide, Carbamate, Urea, and Thiourea Moieties

In order to discover potential ryanodine receptor insecticides, 21 novel anthranilic diamides analogues (C, D, E, and F) containing amide, carbamate, urea, and thiourea moieties were designed and synthesized based on bioisosteric approach. The biological assays against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that these compounds displayed moderate to excellent activities. Especially, compound D-1 showed 100% larvicidal activities against oriental armyworm at 1.0 mg center dot L-1, equivalent to the standard chlorantraniliprole (100%, 1.0 mg center dot L-1). Moreover, the larvicidal activity of D-1 against diamondback moth was 100% at 0.1 mg center dot L-1, more effective than that of chlorantraniliprole (90%, 0.1 mg center dot L-1). Therefore, D-1 can be used as a new lead structure for the development of insecticidal agents. The preliminary structure-activity relationship showed that the introduction od carbamate groups into 4-position on the benzene ring of the N-phenylpyrazole moiety has a positive effect on the larvicidal activities.