Synthesis and Insecticidal Evaluation of Novel N‐pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4‐Oxadiazole Moieties

Abstract

Two series of novel N‐pyridylpyrazole derivatives containing diacylhydrazine/1,3,4‐oxadiazole moieties were designed and synthesized based on the structure of chlorantraniliprole and characterized via 1H‐NMR, 13C‐NMR, IR, MS, and elemental analysis. The preliminary bioassay indicated that some of the title compounds I and II exhibited larvicidal activities against Mythimna separata with 90–100% death rates at 500 mg/L. The further test showed that these compounds had weak insecticidal activity against Mythimna separata and Plutella xylostella at 200 mg/L and might be not suitable as insecticide lead compound for further optimization.

Synthesis and Insecticidal Evaluation of Novel Anthranilic Diamides Derivatives Containing 4‐Chlorine Substituted N‐Pyridylpyrazole

“…Many research groups have devoted considerable efforts to a number of structural modifications since the introduction of diamide insecticides into the world market to date. Most of the modifications were mainly aimed at the following three parts: the aliphatic amide moiety 1 , [ 11‐14 ]] the amide bridge moiety 2 [ 15‐18 ] and the N ‐pyridylpyrazole moiety 3 (Figure 2, C). [ 19‐23] It is well acknowledged that the introduction of halogens into molecule has been regarded as the effective method for pesticide designs due to their chemical and biological characteristics.…”

Design, synthesis and biological activity of diamide compounds based on 3‐substituent of the pyrazole ring†

“…Thus, the development of novel diamide insecticides has mainly concentrated on the modification of the anthranilic diamides 12 . The vast majority of structural modifications have focused on the following three parts: (a) aliphatic amide, (b) anthranilamide and (c) N ‐pyridinedipyrazole, while the 2‐chloro pyridylpyrazole moiety of CHL was largely retained unchanged 13–18 . Previously, our group discovered some compounds with favorable activity against Mythinma separata (oriental armyworm) when nitrobenzene was used to substitute the pyridine moiety of CHL.…”

Antibacterial and Antiviral Activities of 1,3,4-Oxadiazole Thioether 4H-Chromen-4-one Derivatives

“…Among the important five-membered nitrogen-containing heterocyclic compounds, 1,3,4-oxadiazole is one of them, and there are many studies on it in medicines , and organic syntheses . Since the 1,3,4-oxadiazole skeleton has multiple functional building blocks, it has been extensively researched and developed in the process of biologically active recombination. − In addition, 1,3,4-oxadiazole derivatives also exhibit anticancer, antibacterial, antiviral, antifungal, insecticidal, and other biological activities.…”

“…25 Since the 1,3,4-oxadiazole skeleton has multiple functional building blocks, it has been extensively researched and developed in the process of biologically active recombina-tion. 26−28 In addition, 1,3,4-oxadiazole derivatives also exhibit anticancer, 29 antibacterial, 30 antiviral, 31 antifungal, 32 insecticidal, 33 and other biological activities.…”