title: Synthesis and insecticidal evaluation of novel N-pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position.
abstract: In an attempt to search for potent insecticides targeting the ryanodine receptor (RyR), a series of novel N-pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position were designed and synthesized. Their insecticidal activities of target compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentrations. In particular, compound 6l and 6o showed 86% larvicidal activities against Plutella xylostella at the concentration of 0.1mg/L, while the activity of compound 6h against Mythimna separate was 80% at 1mg/L. The calcium imaging technique was applied to investigate the effects of some title compounds on the intracellular calcium ion concentration ([Ca(2+)](i)), experimental results demonstrated that compound 6h stimulates a transient elevation in [Ca(2+)](i) in the absence of external calcium after the central neurons dye loading with fluo-3 AM. However, when the central neurons were dyed with fluo-5N and incubated with 2-APB, [Ca(2+)]i decreased transiently by treated of compound 6h. All of the calcium imaging technique experiments demonstrated that these novel compounds deliver calcium from endoplasmic reticulum to cytoplasm, which proved that the title compounds were the possible activators of insect RyR.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Mingzhen
authors.initials: M
authors.lastname: Mao
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Li
authors.forename: Qiaoxia
authors.initials: Q
authors.lastname: Liu
authors.forename: Yunyun
authors.initials: Y
authors.lastname: Zhou
authors.forename: Xiulan
authors.initials: X
authors.lastname: Zhang
authors.forename: Lixia
authors.initials: L
authors.lastname: Xiong
authors.forename: Yongqiang
authors.initials: Y
authors.lastname: Li
authors.forename: Zhengming
authors.initials: Z
authors.lastname: Li
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D002118:Calcium / Q000378:metabolism; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D007814:Larva / Q000187:drug effects; D009036:Moths / Q000187:drug effects / Q000254:growth & development; D011720:Pyrazoles / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D019837:Ryanodine Receptor Calcium Release Channel / Q000737:chemistry / Q000378:metabolism
chemical_list: D000577:Amides; D007306:Insecticides; D011720:Pyrazoles; D011725:Pyridines; D019837:Ryanodine Receptor Calcium Release Channel; C031280:pyrazole; C023666:pyridine; D002118:Calcium