Synthesis and In Vitro and In Vivo Biological Activity Evaluation and Quantitative Proteome Profiling of Oxadiazoles Bearing Flexible Heterocyclic Patterns

• DOI: 10.1021/acs.jafc.9b02734
• Publication Date: 2019-06-18T19:21:37Z
• Authors: Qing-Qing Tao; Li-Wei Liu; Pei-Yi Wang; Qing-Su Long; Yong-Liang Zhao; Lin-Hong Jin; Wei-Ming Xu; Yang Chen; Zhong Li; Song Yang
• Keywords: Proteomics; Oxadiazoles; 0303 health sciences; Xanthomonas; Molecular Structure; Antinematodal Agents; Microbial Sensitivity Tests; Plants; Anti-Bacterial Agents; Fungicides, Industrial; Structure-Activity Relationship; 03 medical and health sciences; Anti-Infective Agents; Heterocyclic Compounds; Microscopy, Electron, Scanning; Animals; Botrytis; Tylenchoidea; Plant Diseases

A novel series of simple 1,3,4-oxadiazoles that bear flexible heterocyclic patterns was prepared, and their biological activities in plant pathogenic bacteria, fungi, oomycetes, and Meloidogyne incognita in vitro and in vivo were screened to explore low-cost and versatile antimicrobial agents. Screening results showed that compounds, such as A0, B0, and C4, were bioactive against Xanthomonas oryzae pv oryzae in vitro and in vivo, and such bioactivities were superior to those of commercial agents bismerthiazol and thiodiazole copper. Their antibacterial mechanisms were further investigated by quantitative proteomics and concentration-dependent scanning electron microscopy images. Antifungal results indicated that compound A0 displayed a selective and better antifungal effect on Botrytis cinerea with inhibition rate of 96.8% at 50 μg/mL. Nematocidal bioassays suggested that compound D1 had good in vitro nematocidal activity toward M. incognita at 24, 48, and 72 h, with the corresponding insecticidal efficiency of 48.7%, 64.1%, and 87.2% at 40 μg/mL. In vivo study further confirmed that compounds D1 and F2 showed nematocidal actions at 80 μg/mL with a disease index of 1.5. Given these advantages, this kind of molecular frameworks could be a suitable platform for exploring highly efficient agrochemicals.