Design, Synthesis, and Insecticidal Evaluation of N-Pyridylpyrazole Amide Derivatives Containing 4,5-Dihydroisoxazole Amide as Potential Ryanodine Receptor Activators.

Using the 4,5-dihydroisoxazol amide structure to expand the aliphatic amide moiety of chlorantraniliprole, a series of 28 novel N-pyridylpyrazolecarboxamide derivatives containing 4,5-dihydroisoxazol amide fragment were designed and synthesized. All target compounds had been properly characterized and confirmed by 1H NMR, 13C NMR, and HRMS, and the effects were evaluated against Mythimna separata (M. separata) and Plutella xylostella (P. xylostella). The bioassay results indicated that most of the target compounds exhibited good insecticidal activities against M. separata and P. xylostella at 50 mg/L; especially, compound A4 showed an LC50 value of 3.27 mg/L against M. separata. Calcium imaging experiments indicated that the target compound A4 had a similar mechanism of action to chlorantraniliprole, causing an increase in the cytoplasmic Ca2+ concentration. The molecular docking revealed the possible binding mode of compound A4 with a ryanodine receptor.

CF2DSO2Na: An Effective Precursor Reagent for Deuteriodifluoromethylthiolation and Deuteriodifluoromethylation.

Deuteriodifluoromethythio (SCF2D) and deuteriodifluoromethyl (CF2D) are important functional groups in pharmaceutical and agrochemical compounds, and the introduction of these functional groups remains a challenging. We herein report a robust reagent for deuteriodifluoromethylthiolation and deuteriodifluoromethylation. Its potentials were successfully showcased by deuteriodifluoromethylation and deuteriodifluoromethylthiolation of indoles with high-level deuterium incorporation. The reagent also has potential for deuteriodifluoromethylation and deuteriodifluoromethylthiolation of wide range of other natural or synthetic bioactive molecules.