Synthesis, insecticidal activity, structure-activity relationship (SAR) and density functional theory (DFT) of novel anthranilic diamides analogs containing 1,3,4-oxadiazole ringsElectronic supplementary information (ESI) available: Characterization data of compounds 5a-x, general synthetic methods and schemes for intermediates 3a-f, crystal and structure refinement data of compound 5u, 1H NMR spectra and mass spectra for all target compounds 5a-x, and the data for DFT calculation. CCDC 990869.

A series of anthranilic diamides analogs ( 5a-x ) containing 1,3,4-oxadiazole rings were synthesized and characterized by 1 H NMR, 13 C NMR and mass spectrometry. The structure of N -(4-chloro-2-methyl-6-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)methacrylamide ( 5u ) was determined by X-ray diffraction crystallography. The insecticidal activities of these new compounds against diamondback moth ( Plutella xylostella ) were evaluated. Preliminary bioassays indicated that some of these compounds exhibited good insecticidal activities against P. xylostella , especially 3-bromo- N -(4-bromo-2-methyl-6-(5-(pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)-1-(3-chloropyridin-2-yl)-1 H -pyrazole-5-carboxamide ( 5d ), which displayed 100%, 80.95% and 57.14% activity against P. xylostella at 40 μg mL −1 , 10 μg mL −1 and 4 μg mL −1 , respectively. The relationship between structure and insecticidal activity was discussed. The density functional theory (DFT) studies could be helpful to understand the various insecticidal activities. A series of anthranilic diamides analogs ( 5a-x ) containing 1,3,4-oxadiazole rings were synthesized, and their insecticidal activities were evaluated. The density functional theory (DFT) studies was used to understand the various insecticidal activities.