Synthesis and Insecticidal Evaluation of Novel N-Pyridylpyrazolecarboxamides Containing an Amino Acid Methyl Ester and Their Analogues

Abstract

On the basis of the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazolecarboxamides containing an amino acid methyl ester and their analogues were designed and synthesized. Their chemical structures were established on the basis of corresponding (1) H NMR spectroscopy, (13)C NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds against oriental armyworm ( Mythimna separata ) and diamondback moth ( Plutella xylostella ) were evaluated. The results of bioassays indicated that most of the compounds showed moderate to high activities at the tested concentration, of which the compounds 6 containing a methyl acrylate substructure had excellent larvicidal activity; for example, 6a displayed 100% larvicidal activity against P. xylostella at the concentration of 0.005 mg/L, whereas the activities of both compounds 6g and 6h against M. separata were 100% at 2.5 mg/L. The calcium imaging technique experiment results showed that novel compound 6 could elevate the calcium concentration in the cytoplasm. Furthermore, this study also provided evidence that compound 6h activates inositol 1,4,5-trisphosphate (IP3) sensitive intracellular calcium release channels in the endoplasmic reticulum of Spodoptera exigua third-instar larva neurons.

Synthesis, insecticidal evaluation and 3D‐QSAR study of novel anthranilic diamide derivatives as potential ryanodine receptor modulators

“…Most modifications were focused on the aliphatic amide moiety (Fig. , A part I), anthraniloyl moiety (Fig. , A part II), and the pyrazole moiety (Fig.…”

Turning renewable resources into value-added products: Development of rosin-based insecticide candidates

“…The insecticidal activity of rosin-based amide derivatives containing thiadiazole group against M. separata was assessed in line with the reported methods (Mao et al, 2014;Zhang et al, 2012). Briefly, 5 cm diameter leaf disks were prepared from fresh leaves of corn.…”

Structure‐based bioisosterism design, synthesis, insecticidal activity and structure–activity relationship (SAR) of anthranilic diamide analogues containing 1,2,4‐oxadiazole rings

“…Previously, researchers have focused mainly on the substitutions at part (A) and Part (B) . As for the aliphatic amide moiety, most modifications have kept the carbonyl group and replaced the amino with a hydrazide group, a hydrazone group, an amino acid methyl ester, etc . while changes of the amide have not been fully reported.…”