title: 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.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Ming-Zhen
authors.initials: MZ
authors.lastname: Mao
authors.forename: Yu-Xin
authors.initials: YX
authors.lastname: Li
authors.forename: Yun-Yun
authors.initials: YY
authors.lastname: Zhou
authors.forename: Xiu-Lan
authors.initials: XL
authors.lastname: Zhang
authors.forename: Qiao-Xia
authors.initials: QX
authors.lastname: Liu
authors.forename: Feng-Juan
authors.initials: FJ
authors.lastname: Di
authors.forename: Hai-Bin
authors.initials: HB
authors.lastname: Song
authors.forename: Li-Xia
authors.initials: LX
authors.lastname: Xiong
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Li
authors.forename: Zheng-Ming
authors.initials: ZM
authors.lastname: Li
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D004952:Esters / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects* / Q000254:growth & development; D013329:Structure-Activity Relationship; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*
chemical_list: D000596:Amino Acids; D004952:Esters; D007306:Insecticides; D062367:ortho-Aminobenzoates; C517733:chlorantranilipole