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

doi:10.1007/s40242-020-0160-9

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (6): 1190-1195.doi: 10.1007/s40242-020-0160-9

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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

LI Fengyun¹, GONG Jianing¹, LIU Jingbo^2,3, LI Yuxin³, LI Zhengming³

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;
2. College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, P. R. China;
3. State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China

Received:2020-05-27 Revised:2020-07-03 Online:2020-12-01 Published:2020-07-21
Contact: LIU Jingbo, LI Yuxin E-mail:liujingbo0626@163.com;liyx128@nankai.edu.cn
Supported by:
Supported by the Scientific Project of Tianjin Municipal Education Commission, China(No.2018KJ008).

Abstract

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.

Key words: Strobilurin, 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide, Fungicidal activity, CoMSIA model

LI Fengyun, GONG Jianing, LIU Jingbo, LI Yuxin, LI Zhengming. Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates[J]. Chemical Research in Chinese Universities, 2020, 36(6): 1190-1195.

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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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