Non-food bioactive products: Diversified invention of 1,2,4-oxadiazole-containing amide derivatives for novel fungicidal candidate discovery

Hu, Yuge; Gao, Yanqing; Wang, Yujia; Zhang, Wenguang; Liu, Hanru; Zhang, Xingjia; Ma, Zhiqing; Liu, Xili; Lei, Peng

doi:10.1016/j.indcrop.2022.115087

Cited by 12 publications

(14 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to frontier molecular orbital theory, the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) are the most important factors affecting electron transition and can provide useful information about the biological mechanism. 30 As shown in Figure 5, the HOMOs of compounds 10o and 10h showed similar distribution trends. The LUMO distribution of compound 10o was more concentrated than that of compound 10h; therefore, a relatively concentrated LUMO is favored over a dispersed distribution for better insecticidal activity.…”

Section: Insecticidal Activity Of Target Compounds Against M Separata...mentioning

confidence: 57%

Section: Resultsmentioning

confidence: 93%

“…The electrostatic potential reflects the density of electrons and is a relevant structural feature in the action mechanism . Overall, the charge densities are high on oxygen, sulfur, and the isoxazoline ring (Figure ), which mainly donate electrons in the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 10o and 10h with good and poor insecticidal performances, respectively, were chosen as typical molecules for the theoretical calculations. The test method was used as previously reported …”

Section: Methodsmentioning

confidence: 99%

“…The test method was used as previously reported. 30 Homology Modeling and Molecular Docking. Using an online protein structure prediction server, the 3D structure of P. xylostella GABAR was constructed by homology modeling.…”

Section: Insecticidal Activity Of Target Compounds Against M Separata...mentioning

confidence: 99%

See 4 more Smart Citations

Structural Diversity Design, Synthesis, and Insecticidal Activity Analysis of Ester-Containing Isoxazoline Derivatives Acting on the GABA Receptor

Zhang

Yuan

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

To explore insecticides targeting the γ-aminobutyric acid (GABA) receptor, two series of novel isoxazoline derivatives containing sulfonic and carboxylic esters were designed and synthesized. Their insecticidal activities against Plutella xylostella, Mythimna separata, and Aedes aegypti larvae and their structure–activity relationship were investigated. The sulfonate-containing isoxazoline derivatives (10k–q) exhibited promising insecticidal activities against the three insect larvae. Compound 10o displayed excellent activities with LC50 values of 8.32, 5.23, and 0.35 μg/mL at 48 h against P. xylostella, M. separata, and A. aegypti larvae, respectively, which were better than or similar to those of avermectin. Furthermore, compound 10o exhibited a faster insecticidal effect than avermectin against M. separata. The mode of action of 10o was preliminarily verified by molecular docking, theoretical calculations, and measurement of glutamate decarboxylase and glutamic pyruvic transaminase activities. Compound 10o is a novel insecticidal candidate acting on GABA receptors, which could guide the discovery of isoxazoline insecticides.

show abstract

Section: Insecticidal Activity Of Target Compounds Against M Separata...mentioning

confidence: 57%

Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Insecticidal Activity Of Target Compounds Against M Separata...mentioning

confidence: 99%

See 3 more Smart Citations

Structural Diversity Design, Synthesis, and Insecticidal Activity Analysis of Ester-Containing Isoxazoline Derivatives Acting on the GABA Receptor

Zhang

Yuan

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

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

Li,

Hui,

et al. 2024

Pest Management Science

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Design, synthesis and biological activity evaluation of eco‐friendly rosin‐based fungicides for sustainable crop protection

Xu,

Kong,

Lou

et al. 2024

Pest Management Science

View full text Add to dashboard Cite

BACKGROUNDUtilizing fungicides to protect crops from diseases is an effective method, and novel eco‐friendly plant‐derived fungicides with high efficiency and low toxicity are urgent requirements for sustainable crop protection.RESULTTwo series of rosin‐based fungicides (totally 35) were designed and synthesized. In vitro fungicidal activity revealed that Compound 6a (Co. 6a) effectively inhibited the growth of Valsa mali [median effective concentration (EC50) = 0.627 μg mL−1], and in vivo fungicidal activity suggested a significant protective efficacy of Co. 6a in protecting both apple branches (35.12% to 75.20%) and apples (75.86% to 90.82%). Quantum chemical calculations (via density functional theory) results indicated that the primary active site of Co. 6a lies in its amide structure. Mycelial morphology and physiology were investigated to elucidate the mode‐of‐action of Co. 6a, and suggested that Co. 6a produced significant cell membrane damage, accelerated electrolyte leakage, decreased succinate dehydrogenase (SDH) protein activity, and impaired physiological and biochemical functions, culminating in mycelial mortality. Molecular docking analysis revealed a robust binding energy (ΔE = −7.29 kcal mol−1) between Co. 6a and SDH. Subsequently, biosafety evaluations confirmed the environmentally‐friendly nature of Co. 6a via the zebrafish model, yet toxicological results indicated that Co. 6a at median lethal concentration [LC50(96)] damaged the gills, liver and intestines of zebrafish.CONCLUSIONThe above research offers a theoretical foundation for exploiting eco‐friendly rosin‐based fungicidal candidates in sustainable crop protection. © 2024 Society of Chemical Industry.

show abstract

Non-food bioactive products: Diversified invention of 1,2,4-oxadiazole-containing amide derivatives for novel fungicidal candidate discovery

Cited by 12 publications

References 44 publications

Structural Diversity Design, Synthesis, and Insecticidal Activity Analysis of Ester-Containing Isoxazoline Derivatives Acting on the GABA Receptor

Structural Diversity Design, Synthesis, and Insecticidal Activity Analysis of Ester-Containing Isoxazoline Derivatives Acting on the GABA Receptor

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

Design, synthesis and biological activity evaluation of eco‐friendly rosin‐based fungicides for sustainable crop protection

Contact Info

Product

Resources

About