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.
Subject(s)
Insecticides/chemistry , Insecticides/toxicity , Moths/drug effects , ortho-Aminobenzoates/chemistry , ortho-Aminobenzoates/toxicity , Amino Acids/chemistry , Animals , Esters/chemistry , Insecticides/chemical synthesis , Larva/drug effects , Molecular Structure , Moths/growth & development , Structure-Activity Relationship , ortho-Aminobenzoates/chemical synthesisABSTRACT
In an attempt to search for potent antifungal agents, a series of novel 1-substituted phenyl-4-[N-[(2'-morpholinothoxy)phenyl]aminomethyl]-1H-1,2,3-triazoles 5a-m was designed and synthesized via Huisgen cycloaddition reaction between various (2-morpholinoethoxy)-N-(prop-2-ynyl)aniline and different azidobenzene. Their chemical structures were characterized by (1) H NMR and elemental analysis. A cleaner reaction with milder conditions and satisfactory yields was observed in the micorwave-assisted synthesis of 4a-c. The fungicidal activity of some target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Cercospora arachidicola and Gibberella zeae at 50 µg/mL. The bioassay results indicated that some compounds exhibited moderate fungicidal activities. Furthermore, compound 5h displayed equal activity to the positive control compounds against Alternaria solani.
