Discovery of novel salicylaldehyde derivatives incorporating an <scp>α‐methylene‐γ‐butyrolactone</scp> moiety as fungicidal agents

He, Hong‐Wei; Xu, Dan; Wu, K. K.; Lu, Zhiqiang; Liu, Xili; Xu, Gong

doi:10.1002/ps.7703

Cited by 7 publications

(3 citation statements)

References 52 publications

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“…The inoculation methods for R. solani have been previously documented. 35,36 In Vivo Antifungal Activities against B. cinerea. Based on the in vitro antifungal activity test, compound C24 against B. cinerea were further evaluated in vivo on tomato.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

Chen,

Jiang,

Tong

et al. 2024

J. Agric. Food Chem.

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In this study, a series of novel hydrazide-containing flavonol derivatives was designed, synthesized, and evaluated for antifungal activity. In the in vitro antifungal assay, most of the target compounds exhibited potent antifungal activity against seven tested phytopathogenic fungi. In particular, compound C32 showed the best antifungal activity against Rhizoctonia solani (EC 50 = 0.170 μg/mL), outperforming carbendazim (EC 50 = 0.360 μg/mL) and boscalid (EC 50 = 1.36 μg/mL). Compound C24 exhibited excellent antifungal activity against Valsa mali, Botrytis cinerea, and Alternaria alternata with EC 50 values of 0.590, 0.870, and 1.71 μg/ mL, respectively. The in vivo experiments revealed that compounds C32 and C24 were potential novel agricultural antifungals. 3D quantitative structure−activity relationship (3D-QSAR) models were used to analyze the structure−activity relationships of these compounds. The analysis results indicated that introducing appropriate electronegative groups at position 4 of a benzene ring could effectively improve the anti-R. solani activity. In the antifungal mechanism study, scanning electron microscopy and transmission electron microscopy analyses revealed that C32 disrupted the normal growth of hyphae by affecting the structural integrity of the cell membrane and cellular respiration. Furthermore, compound C32 exhibited potent succinate dehydrogenase (SDH) inhibitory activity (IC 50 = 8.42 μM), surpassing that of the SDH fungicide boscalid (IC 50 = 15.6 μM). The molecular dynamics simulations and docking experiments suggested that compound C32 can occupy the active site and form strong interactions with the key residues of SDH. Our findings have great potential for aiding future research on plant disease control in agriculture.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

Chen,

Jiang,

Tong

et al. 2024

J. Agric. Food Chem.

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“…Effect of the enzyme activity of complex III on R. solani Based on earlier studies, we found that one of the targets of carabrone is mitochondrial complex III. [30][31][32] Thus, MBL derivatives containing benzothiophene fragments may also target mitochondrial complex III because they share the same pharmacophore. The mycelia of R. solani were treated with compound 2 and famoxadone at concentrations of 25 and 50 mg L −1 , respectively, and the untreated mycelia served as a blank control.…”

Section: Relative Conductivity %mentioning

confidence: 99%

Design, synthesis and antifungal activity of novel α‐methylene‐γ‐butyrolactone derivatives containing benzothiophene moiety

Li,

Hui,

et al. 2024

Pest Management Science

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BackgroundThe discovery of agricultural fungicide candidates from natural products is one of the key strategies to develop environment friendly agricultural fungicides with high efficiency, high selectivity, and unique mechanisms of action. Based on previous work, a series of novel α‐methylene‐γ‐butyrolactone (MBL) derivatives containing benzothiophene moiety were designed and synthesized.ResultsThe majority of the proposed compounds displayed moderate to considerable antifungal efficacy against the tested pathogenic fungi and oomycetes, some exhibiting broad spectrum antifungal activity. Notably, compounds 2 (3‐F‐Ph) and 7 (4‐Cl‐Ph) showed excellent antifungal activity against R. solani with EC50 values of 0.94 and 0.99 mg/L, respectively, comparable to the commercial fungicide tebuconazole (EC50 = 0.96 mg/L), and also displayed significant inhibitory effects against V. mali with EC50 values of 2.26 and 1.67 mg/L, respectively, better than famoxadone and Carabrone. The in vivo protective and curative effects against R. solani of compound 2 were 57.2% and 53.7% at 100 mg/L, respectively, which were equivalent to tebuconazole (51.6% and 52.4%). Further investigations found that compound 2 altered the ultrastructure of R. solani cell, significantly increased the relative conductivity of the cells, and reduced the activity of complex III in a dose‐dependent manner. Molecular docking results showed that compound 2 matched well with the Qo pocket.ConclusionThe results revealed that MBL derivatives containing benzothiophene moiety are promising antifungal candidates and provide a new backbone structure for further optimization of novel fungicides.This article is protected by copyright. All rights reserved.

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“…Plant pathogens seriously affect food security and yield, and the use of fungicides is the most direct and effective way to control crop diseases. , According to FRAC, more than 230 small-molecule fungicides are currently commercialized, providing a guarantee for a global food supply and social security and stability. However, with the long-term use of traditional chemical fungicides, pathogen resistance is becoming more and more serious, and the ecological environment is also under threat. − Therefore, the development of new, green, safe, and efficient fungicides is indispensable and also in line with the concept of green sustainable development.…”

Section: Introductionmentioning

confidence: 99%

Environmental Evaluation on Toxicity, Toxic Mechanism, and Hydrolysis Behavior of Potential Acethydrazide Fungicide Candidates

Chen,

Chang,

Wang

et al. 2024

J. Agric. Food Chem.

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The evaluation of toxicity and environmental behavior of bioactive lead molecules is helpful in providing theoretical support for the development of agrochemicals, in line with the sustainable development of the ecological environment. In previous work, some acethydrazide structures have been demonstrated to exhibit excellent and broad-spectrum fungicidal activity; however, its environmental compatibility needs to be further elucidated if it is to be identified as a potential fungicide. In this project, the toxicity of fungicidal acethydrazide lead compounds F51, F58, F72, and F75 to zebrafish was determined at 10 μg mL −1 and 1 μg mL −1 . Subsequently, the toxic mechanism of compound F58 was preliminarily explored by histologic section and TEM observations, which revealed that the gallbladder volume of common carp treated with compound F58 increased, accompanied by a deepened bile color, damaged plasma membrane, and atrophied mitochondria in gallbladder cells. Approximately, F58-treated hepatocytes exhibited cytoplasmic heterogeneity, with partial cellular vacuolation and mitochondrial membrane rupture. Metabolomics analysis further indicated that differential metabolites were enriched in the bile formation-associated steroid biosynthesis, primary bile acid biosynthesis, and taurine and hypotaurine metabolism pathways, as well as in the membrane function-related glycerophospholipid metabolism, linolenic acid metabolism, α-linolenic acid metabolism, and arachidonic acid metabolism pathways, suggesting that the acethydrazide F58 may have acute liver toxicity to common carp. Finally, the hydrolysis dynamics of F58 was investigated, with the obtained half-life of 5.82 days. The above results provide important guiding significance for the development of new green fungicides.

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Discovery of novel salicylaldehyde derivatives incorporating an α‐methylene‐γ‐butyrolactone moiety as fungicidal agents

Cited by 7 publications

References 52 publications

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

Design, synthesis and antifungal activity of novel α‐methylene‐γ‐butyrolactone derivatives containing benzothiophene moiety

Environmental Evaluation on Toxicity, Toxic Mechanism, and Hydrolysis Behavior of Potential Acethydrazide Fungicide Candidates

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