Novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety: design, synthesis, antibacterial and nematocidal activities. 2018

Pei Li, and Pingyi Tian, and Yongzhong Chen, and Xianpeng Song, and Wei Xue, and Linhong Jin, and Deyu Hu, and Song Yang, and Baoan Song
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang, China.

BACKGROUND The literature shows that bisthioether and 1,3,4-oxadiazole derivatives exhibit a wide variety of biological activities. In this study, a series of novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety were synthesized and their antibacterial and nematocidal activities investigated. RESULTS Among the title compounds evaluated, compound 4f demonstrated the best antibacterial activities against rice bacterial leaf blight, rice bacterial leaf streak and citrus canker caused by Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas axonopodis pv. citri (Xac), with EC50 values of 4.82, 11.15 and 16.57 µg mL-1 , respectively, which were even better than those of thiodiazole copper and bismerthiazol. Meanwhile, compound 4f had better in vitro nematocidal activity against Caenorhabditis elegans at 48 h, with an LC50 value of 2.89 µg mL-1 , which was superior to those of ethoprophos and fosthiazate. In addition, greenhouse trials indicated that compound 4f was effective in reducing rice bacterial leaf blight relative to thiodiazole copper and bismerthiazol. CONCLUSIONS A series of novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety were synthesized and bioassay results showed that compound 4f exhibited the best antibacterial and nematocidal activities. © 2017 Society of Chemical Industry.

UI MeSH Term Description Entries
D010069 Oxadiazoles Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms. Oxadiazole
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000900 Anti-Bacterial Agents Substances that inhibit the growth or reproduction of BACTERIA. Anti-Bacterial Agent,Anti-Bacterial Compound,Anti-Mycobacterial Agent,Antibacterial Agent,Antibiotics,Antimycobacterial Agent,Bacteriocidal Agent,Bacteriocide,Anti-Bacterial Compounds,Anti-Mycobacterial Agents,Antibacterial Agents,Antibiotic,Antimycobacterial Agents,Bacteriocidal Agents,Bacteriocides,Agent, Anti-Bacterial,Agent, Anti-Mycobacterial,Agent, Antibacterial,Agent, Antimycobacterial,Agent, Bacteriocidal,Agents, Anti-Bacterial,Agents, Anti-Mycobacterial,Agents, Antibacterial,Agents, Antimycobacterial,Agents, Bacteriocidal,Anti Bacterial Agent,Anti Bacterial Agents,Anti Bacterial Compound,Anti Bacterial Compounds,Anti Mycobacterial Agent,Anti Mycobacterial Agents,Compound, Anti-Bacterial,Compounds, Anti-Bacterial
D000969 Antinematodal Agents Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. Nematocides,Antinematodal Drugs,Antinematodals,Agents, Antinematodal,Drugs, Antinematodal
D013440 Sulfides Chemical groups containing the covalent sulfur bonds -S-. The sulfur atom can be bound to inorganic or organic moieties. Sulfide,Thioether,Thioethers,Sulfur Ethers,Ethers, Sulfur
D014974 Xanthomonas A genus in the family XANTHOMONADACEAE whose cells produce a yellow pigment (Gr. xanthos - yellow). It is pathogenic to plants. Xanthomonas albilineans
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D017173 Caenorhabditis elegans A species of nematode that is widely used in biological, biochemical, and genetic studies. Caenorhabditis elegan,elegan, Caenorhabditis

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