Abstract
Referring to the structural information of the “hit” compound A from the reported pharmacophore-based virtual screening, a series of novel thienylpyridyl- and thioether/sulfoxide/sulfone-containing acetamide derivatives have been designed and synthesized. The structures of new compounds were confirmed by 1H NMR, 13C NMR and HRMS. The single-crystal structure of A was firstly reported. All the new synthesized compounds were evaluated for insecticidal activities on Mythimna separata Walker and Plutella xylostella L. Through a step-by-step structural optimization, the high insecticidal agents, especially towards Plutella xylostella L., have been found, and thienylpyridyl- and sulfone/thioether-containing acetamides Iq, Io, Ib and A, which are comparable with the control insecticides cartap, triflumuron and chlorantraniliprole in the present study, can be used as novel lead structures for new insecticides innovation research. In addition, some of the compounds, e.g., A, Ih, Id, Io and Iq, also exhibited favourable fungicidal activities against Physalospora piricola, Rhizoctonia cerealis and Sclerotinia sclerotiorum and would provide useful guidance for the design and development of new fungicides.
Highlights
As the typical representatives of heterocyclic compounds, pyridine derivatives exhibit a broad range of bioactivity potentials, and many of them have been developed as pharmaceuticals, insecticides, herbicides, fungicides, etc. [5,6,7,8]
According to the the structural structural feature feature of of the the target target molecules molecules designed, designed, there there are are two two According to thethe structural feature of the target nucleophilic molecules designed, there strategies togenerate generate thepyridylthioacetamides—the pyridylthioacetamides―the nucleophilic substitution of two pyristrategies to substitution of are pyridine strategies towith generate the pyridylthioacetamides―the substitution of pyridine halide mercaptoacetamide or pyridine with chloroacetamide. Both methhalide with mercaptoacetamide or pyridine thiolthiol withnucleophilic chloroacetamide
Iq triflumuron chlorantraniliprole y = 8.47 + 1.24x y = 5.31 + 0.71x y = 9.75 + 1.13x. These results indicate that the high-insecticidal agents have been found through a step-by-step structural optimization based on Sindhu’s research and our further validation, design, synthesis and biological evaluations
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. The discovery and development for new agrochemicals with novel structures, excellent biological activities and other beneficial properties are of great significance to agriculture and are continuous subjects for pesticide researchers [1,2,3,4]. Thioethers are one type of organic sulphur compound that hold a variety of biological activities but can provide reaction sites for further derivatizations (such as S to S=O and S(=O)2 ) and for the environmental degradation [12]; for example, fipronil and flubendiamide (Figure 1) are potent insecticides containing sulfoxide and sulfone motif, respectively, [13,14], and both groups are derived from their thioether precursors. Molecules, that is, the experimental validation of their bioassay for those molecules, that is, the experimental validation of their insecticidal bioassay for those “hit” molecules, that is, the experimental validationmolecuof their molecular design results from the pharmacophore-based virtual screening. Enlightened lar design results thefrom pharmacophore-based virtual screening.
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