Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives

Abstract

A pair of chemical isomeric structures of novel N-tert-butylphenyl thenoylhydrazide compounds I and II were designed and synthesized. Their structures were characterized by MS, IR, 1H NMR, elemental analysis and X-ray single crystal diffraction. The regioselectivity of the Meerwein arylation reaction and the electrophilic substitution reaction of N-tert-butyl hydrazine were studied by density functional theory (DFT) quantum chemical method. The larvicidal tests revealed that some compounds I had excellent larvicidal activity against Culex pipiens pallens. As the candidates of insect growth regulators (IGRs), the larval growth inhibition and regulation against Culex pipiens pallens were examined for some compounds, especially I1 and I7. Compounds I1 and I7 were further indicated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). Finally, a molecular docking study of compound I7 was conducted, which was not only beneficial to understand the structure-activity relationship, but also useful for development of new IGRs for the control of mosquitos.

Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

“…N - tert- butyl- N , N′ -dibenzoylhydrazine (RH-5849) exhibited significant insecticidal activity against Mythimna separata and Plutella xylostella (Song et al, 2016). The LC 50 of compound 3c against Culex quinquefasciatus was 6.51 µg/mL, which was highly active compared to N′ - tert- butyl- N , N′ -dibenzoylhydrazine (28.24 µg/mL), and also compared with natural product compounds such as (−)-pinidinol and hydantocidin.…”

Synthesis of novel benzopyran-connected pyrimidine and pyrazole derivatives via a green method using Cu(ii)-tyrosinase enzyme catalyst as potential larvicidal, antifeedant activities

“…The results were analyzed using the statistical software SPSS version 16.0. The larval growth inhibition and regulation against Culex quinquefasciatus were determined using the water immersion method 30 .…”