title: Natural-product-based insecticidal agents 14. Semisynthesis and insecticidal activity of new piperine-based hydrazone derivatives against Mythimna separata Walker in vivo.
abstract: In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, twenty-six new piperine-based hydrazone derivatives were synthesized from piperine, an alkaloid isolated from Piper nigrum Linn. The single-crystal structures of 6c, 6q and 6w were unambiguously confirmed by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 6b, 6i and 6r, the final mortality rates of which, at the concentration of 1 mg/mL, were 62.1%, 65.5% and 65.5%, respectively, exhibited more pronounced insecticidal activity compared to toosendanin at 1 mg/mL, a commercial botanical insecticide isolated from Melia azedarach. It suggested that introduction of the substituents at the C-2 position on the phenyl ring of the hydrazone derivatives was important for their insecticidal activity.
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, PR China.
authors.forename: Huan
authors.initials: H
authors.lastname: Qu
authors.forename: Xiang
authors.initials: X
authors.lastname: Yu
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Zhi
authors.forename: Min
authors.initials: M
authors.lastname: Lv
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000818:Animals; D052117:Benzodioxoles / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D007814:Larva / Q000187:drug effects; D031585:Melia / Q000737:chemistry / Q000378:metabolism; D008968:Molecular Conformation; D009036:Moths / Q000187:drug effects / Q000254:growth & development; D031701:Piper / Q000737:chemistry / Q000378:metabolism; D010880:Piperidines / Q000737:chemistry*; D053284:Polyunsaturated Alkamides / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D052117:Benzodioxoles; D001688:Biological Products; D006835:Hydrazones; D007306:Insecticides; D010880:Piperidines; D053284:Polyunsaturated Alkamides; C008922:piperine
keywords: Botanical insecticide; Hydrazone; Insecticidal activity; Mythimna separata Walker; Piperine; Structural modification