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. 2020 Jul 31;25(15):3500.
doi: 10.3390/molecules25153500.

Synthesis and Biological Activity of Benzamides Substituted with Pyridine-Linked 1,2,4-Oxadiazole

Sen Yang  1 , Xiao-Yu Tian  1 , Tian-Yang Ma  1 , Li Dai  1 , Chao-Li Ren  1 , Jun-Chang Mei  1 , Xing-Hai Liu  1 , Cheng-Xia Tan  1
Affiliations

Synthesis and Biological Activity of Benzamides Substituted with Pyridine-Linked 1,2,4-Oxadiazole

Sen Yang et al. Molecules. .

Abstract

To find pesticidal lead compounds with high activity, a series of novel benzamides substituted with pyridine-linked 1,2,4-oxadiazole were designed by bioisosterism, and synthesized easily via esterification, cyanation, cyclization and aminolysis reactions. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. The preliminary bioassay showed that most compounds had good larvicidal activities against mosquito larvae at 10 mg/L, especially compound 7a, with a larvicidal activity as high as 100%, and even at 1 mg/L was still 40%; at 50 mg/L, all the target compounds showed good fungicidal activities against the eight tested fungi. Moreover, compound 7h exhibited better inhibitory activity (90.5%) than fluxapyroxad (63.6%) against Botrytis cinereal. Therefore, this type of compound can be further studied.

Keywords: 1,2,4-oxadiazole; amide compound; fungicidal activity; insecticidal activity; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of flufenacet, flubendiamide, flutolanil, chlorantraniliprole and compounds A, B, C.
Figure 2
Figure 2
Design strategy of the target compounds.
Scheme 1
Scheme 1
Synthetic route of target compound 7.
Scheme 2
Scheme 2
Reaction equation of step 4.
See this image and copyright information in PMC

References

    1. Liu X.H., Yu W., Min L.J., Wedge D.E., Tan C.X., Weng J.Q., Wu H.K., Cantrell C.L., Bajsa-Hischel J., Hua X.W., et al. Synthesis and pesticidal activities of new quinoxalines. J. Agric. Food Chem. 2020 doi: 10.1021/acs.jafc.0c01042. - DOI - PubMed
    1. Alnufaie R., Alsup N., Whitt J., Chambers A.S., Gilmore D., Alam A.M. Synthesis and antimicrobial studies of coumarin-substituted pyrazole derivatives as potent anti-staphylococcus aureus agents. Molecules. 2020;25:2758. doi: 10.3390/molecules25122758. - DOI - PMC - PubMed
    1. Mu J.X., Shi Y.X., Yang M.Y., Sun Z.H., Liu X.H., Li B.J., Sun N.B. Design, Synthesis, DFT Study and Antifungal Activity of Pyrazolecarboxamide Derivatives. Molecules. 2016;21:68. doi: 10.3390/molecules21010068. - DOI - PMC - PubMed
    1. Liu X.H., Qiao L., Zhai Z.W., Cai P.P., Cantrell C.L., Tan C.X., Weng J.Q., Han L., Wu H.K. Novel 4-Pyrazole Carboxamide Derivatives Containing Flexible Chain Motif: Design, Synthesis and Antifungal Activity. Pest Manag. Sci. 2019;75:2892–2900. doi: 10.1002/ps.5463. - DOI - PubMed
    1. Wang L., Dai F.Y., Zhu J., Dong K.K., Wang Y.L., Chen T. Synthesis and antibacterial activities of pleuromutilin derivatives with thiazole-5-carboxamide and thioether moiety. J. Chem. Res. 2011;35:313–316. doi: 10.3184/174751911X13057375208346. - DOI

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