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Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates

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Chemical Research in Chinese Universities Aims and scope

Abstract

To discover novel strobilurins analogues with good and broad spectrum activity, a series of novel 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides-based strobilurins was designed, synthesized, and tested against various phytopathogenic fungi. Compounds 7b, 7c, and 7k exhibited substantial and broad spectrum antifungal activities against the tested phytopathogenic fungi, especially compound 7b, which showed 100%, 80%, 90%, and 90% antifungal activity(in virto) against Erysiphe graminis(E. graminis), Puccinia sorghi Schw.(P. sorghi Schw.), Colletotrichum lagenarium(C. lagenarium), and Pseudoperonospora cubensis(P. cubensis) at 300 µg/mL, respectively, better or comparable to the positive control azoxystrobin. Moreover, compound 7b exhibited 85% greenhouse inhibition activity(in vivo) against E. graminis even at 0.2 µg/mL, equal to azoxystrobin(90%) and trifloxystrobin(90%). Meanwhile, compound 7b against P. cubensis displayed 70% and 55% greenhouse inhibition activity(in vivo) at 1.56 and 0.2 µg/mL, respectively, much better than those of azoxystrobin and trifloxystrobin(both 0% at 1.56 and 0.2 µg/mL). Therefore, compound 7b could be considered as the most promising fungicidal candidate for further study. Furthermore, based on the effective concentration(EC50) against C. arachidicola, the built CoMSIA model provided the useful reference for the further structural optimization design.

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Authors and Affiliations

  1. School of Chinese Materia Medica, Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, 300193, P. R. China

    Fengyun Li & Jianing Gong

  2. College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin, 300384, P. R. China

    Jingbo Liu

  3. State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P. R. China

    Jingbo Liu, Yuxin Li & Zhengming Li

Authors
  1. Fengyun Li
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  2. Jianing Gong
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  3. Jingbo Liu
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  4. Yuxin Li
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  5. Zhengming Li
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Corresponding authors

Correspondence to Jingbo Liu or Yuxin Li.

Additional information

Supported by the Scientific Project of Tianjin Municipal Education Commission, China(No.2018KJ008).

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40242_2020_160_MOESM1_ESM.pdf

Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates

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Li, F., Gong, J., Liu, J. et al. Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates. Chem. Res. Chin. Univ. 36, 1190–1195 (2020). https://doi.org/10.1007/s40242-020-0160-9

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  • DOI: https://doi.org/10.1007/s40242-020-0160-9

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