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Synthesis of benzothiazole-appended bis-triazole-based structural isomers with promising antifungal activity against Rhizoctonia solani.

ABSTRACT: In order to explore new antifungal agrochemicals, we reported the synthesis of two series 5a-f, 6 and 7a-f, 8 of benzothiazole-appended bis-triazole derivative-based structural isomers using a molecular hybridization approach. The synthesized compounds were tested for fungal growth inhibition against the plant pathogen Rhizoctonia solani. All the synthesized compounds showed excellent antifungal activity in their minimum concentrations (10-0.62 μM). Among all the synthetics, compounds 5b (ED₅₀: 2.33 μM), 5f (ED₅₀: 0.96 μM), and 7f (ED₅₀: 1.48 μM) exerted a superior inhibitory effect in comparison to the commercially available fungicide, hexaconazole (ED₅₀: 2.44 μM). The binding interactions of the active compounds 5f, 7f, 6, and 8 within the active site of the sterol 14α-demethylase enzyme were studied with the help of molecular docking studies. The studies revealed that these hybrid pharmacophores could be used as an important intermediate to demonstrate new structural isomer-based fungicides.

SUBMITTER: Upadhyay RK

PROVIDER: S-EPMC9425831 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Synthesis of benzothiazole-appended bis-triazole-based structural isomers with promising antifungal activity against <i>Rhizoctonia solani</i>.

Upadhyay Ravindra Kumar RK Saini Keshav Kumar KK Deswal Nidhi N Singh Tejveer T Tripathi Kailash Pati KP Kaushik Parshant P Shakil Najam Akhtar NA Bharti Alok Chandra AC Kumar Rakesh R

RSC advances 20220830 37

In order to explore new antifungal agrochemicals, we reported the synthesis of two series 5a-f, 6 and 7a-f, 8 of benzothiazole-appended bis-triazole derivative-based structural isomers using a molecular hybridization approach. The synthesized compounds were tested for fungal growth inhibition against the plant pathogen <i>Rhizoctonia solani</i>. All the synthesized compounds showed excellent antifungal activity in their minimum concentrations (10-0.62 μM). Among all the synthetics, compounds 5b ...[more]

PMID: 36128524

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Project description:Pathogenic infestations are significant threats to vegetable yield, and have become an urgent problem to be solved. Rhizoctonia solani is one of the worst fungi affecting tomato crops, reducing yield in some regions. It is a known fact that plants have their own defense against such infestations; however, it is unclear whether any exogenous material can help plants against infestation. Therefore, we performed greenhouse experiments to evaluate the impacts of R. solani on 15- and 30-day old tomato plants after fungal infestation, and estimated the antifungal activity of nanoparticles (NPs) against the pathogen. We observed severe pathogenic impacts on the above-ground tissues of tomato plants which would affect plant physiology and crop production. Pathogenic infection reduced total chlorophyll and anthocyanin contents, which subsequently disturbed plant physiology. Further, total phenolic contents (TPC), total flavonoid contents (TFC), and malondialdehyde (MDA) contents were significantly increased in pathogen treatments. Constitutively, enhanced activities were estimated for catalase (CAT), superoxide dismutase (SOD), and ascorbate peroxidase (APX) in response to reactive oxygen species (ROS)in pathogen-treated plants. Moreover, pathogenesis-related genes, namely, chitinase, plant glutathione S-transferase (GST), phenylalanine ammonia-lyase (PAL1), pathogenesis-related protein (PR12), and pathogenesis-related protein (PR1) were evaluated, with significant differences between treated and control plants. In vitro and greenhouse antifungal activity of silver nanoparticles (Ag NPs), chitosan nanoparticles, and Ag NPs/CHI NPs composites and plant health was studied using transmission electron microscopy (TEM) and Fourier transform infrared (FTIR) spectrophotometry. We found astonishing results, namely, that Ag and CHI have antifungal activities against R. solani. Overall, plant health was much improved following treatment with Ag NPs/CHI NPs composites. In order to manage R. solani pathogenicity and improve tomato health, Ag/CHI NPs composites could be used infield as well as on commercial levels based on recommendations. However, there is an urgent need to first evaluate whether these NP composites have any secondary impacts on human health or the environment.

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Synthesis of benzothiazole-appended bis-triazole-based structural isomers with promising antifungal activity against Rhizoctonia solani.

Publications

Synthesis of benzothiazole-appended bis-triazole-based structural isomers with promising antifungal activity against <i>Rhizoctonia solani</i>.

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