Design, synthesis, and antifungal activity of novel dithiin tetracarboximide derivatives as potential succinate dehydrogenase inhibitors

被引:5
作者
Ma, Zhi [2 ,3 ]
Qiu, Shuo [2 ,3 ]
Zhang, Dong [2 ,3 ]
Guo, Xinying [2 ,3 ]
Lu, Yuele [2 ,3 ]
Fan, Yongxian [4 ]
Chen, Xiaolong [1 ,2 ,3 ]
机构
[1] Zhejiang Univ Technol, Inst Fermentat Engn, 18 Chaowang Rd, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Inst Fermentat Engn, Hangzhou, Peoples R China
[3] Zhejiang Univ Technol, Coll Biotechnol & Bioengn, Hangzhou, Peoples R China
[4] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou, Peoples R China
基金
中国国家自然科学基金;
关键词
succinate dehydrogenase inhibitor; dithiin tetracarboximide derivatives; antifungal activity; SDH inhibition assay; molecular docking; CARBOXAMIDE; CHALLENGES; FUNGICIDES; RESISTANCE; DISCOVERY; SERIES; ALKYL;
D O I
10.1002/ps.7369
中图分类号
S3 [农学(农艺学)];
学科分类号
0901 ;
摘要
BACKGROUNDSuccinate dehydrogenase inhibitor (SDHI) fungicides are an important class of agricultural fungicides with the advantages of high efficiency and a broad bactericidal spectrum. To pursue novel SDHIs, a series of N-substituted dithiin tetracarboximide derivatives were designed, synthesized, and characterized by H-1 NMR, C-13 NMR, and high resolution mass spectrum (HRMS). RESULTSThese engineered compounds displayed potent fungicidal activity against phytopathogens, including Sclerotinia sclerotiorum, Botrytis cinerea, and Rhizoctonia solani, comparable with that of the commercial SDHI fungicide boscalid. In particular, compound 18 stood out with prominent activity against S. sclerotiorum with a half-maximal effective concentration (EC50) value of 1.37 mu g ml(-1). Compound 1 exhibited the most potent antifungal activity against B. cinerea with EC50 values of 5.02 mu g ml(-1). As for R. solani, 12 and 13 exhibited remarkably inhibitory activity with EC50 values of 4.26 and 5.76 mu g ml(-1), respectively. In the succinate dehydrogenase (SDH) inhibition assay, 13 presented significant inhibitory activity with a half-maximal inhibitory concentration (IC50) value of 15.3 mu m, which was approximately equivalent to that of boscalid (14.2 mu m). Furthermore, molecular docking studies revealed that 13 could anchor in the binding site of SDH. CONCLUSIONTaken together, results suggested that the dithiin tetracarboximide scaffold possessed a huge potential to be developed as novel fungicides and SDHIs. (c) 2023 Society of Chemical Industry.
引用
收藏
页码:1922 / 1930
页数:9
相关论文
共 42 条
[1]   Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species: I. Taxonomy, fermentation, isolation and biological activities [J].
Al-Zereini, Wael ;
Yao, Clarisse Blanchine Fotso Fondja ;
Laatsch, Hartmut ;
Anke, Heidrun .
JOURNAL OF ANTIBIOTICS, 2010, 63 (06) :297-301
[2]  
Baibakova EV., 2019, ANN RES REV BIOL, V32, P1, DOI DOI 10.9734/ARRB/2019/V32I330083
[3]   Multiple resistance of Botrytis cinerea from kiwifruit to SDHIs, QoIs and fungicides of other chemical groups [J].
Bardas, George A. ;
Veloukas, Thomas ;
Koutita, Olga ;
Karaoglanidis, George S. .
PEST MANAGEMENT SCIENCE, 2010, 66 (09) :967-973
[4]   Characterization of Monilinia fructicola Strains Resistant to Both Propiconazole and Boscalid [J].
Chen, F. ;
Liu, X. ;
Chen, S. ;
Schnabel, E. ;
Schnabel, G. .
PLANT DISEASE, 2013, 97 (05) :645-651
[5]   Graphene Oxide-Silver Nanocomposite: Novel Agricultural Antifungal Agent against Fusarium graminearum for Crop Disease Prevention [J].
Chen, Juanni ;
Sun, Long ;
Cheng, Yuan ;
Lu, Zhicheng ;
Shao, Kang ;
Li, Tingting ;
Hu, Chao ;
Han, Heyou .
ACS APPLIED MATERIALS & INTERFACES, 2016, 8 (36) :24057-24070
[6]  
Chen X, 2017, VALIDAMYCIN AND ITS DERIVATIVES: DISCOVERY, CHEMICAL SYNTHESIS, AND BIOLOGICAL ACTIVITY, P1
[7]   Synthesis and antifungal evaluation of a series of maleimides [J].
Chen, Xiao-Long ;
Zhang, Li-Jun ;
Li, Fu-Ge ;
Fan, Yong-Xian ;
Wang, Wei-Ping ;
Li, Bao-Ju ;
Shen, Yin-Chu .
PEST MANAGEMENT SCIENCE, 2015, 71 (03) :433-440
[8]   Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate Kinase [J].
Dong, Jingyue ;
Gao, Wei ;
Li, Kun ;
Hong, Zeyu ;
Tang, Liangfu ;
Han, Lijun ;
Wang, Zhihong ;
Fan, Zhijin .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2022, 70 (11) :3435-3446
[9]   Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita [J].
Eloh, Kodjo ;
Demurtas, Monica ;
Mura, Manuel Giacomo ;
Deplano, Alessandro ;
Onnis, Valentina ;
Sasanelli, Nicola ;
Maxia, Andrea ;
Caboni, Pierluigi .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2016, 64 (24) :4876-4881
[10]   Structure-antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid [J].
Farhoosh, Reza ;
Johnny, Saeed ;
Asnaashari, Maryam ;
Molaahmadibahraseman, Najme ;
Sharif, Ali .
FOOD CHEMISTRY, 2016, 194 :128-134