Design, synthesis, insecticidal activities, and molecular docking of novel pyridylpyrazolo carboxylate derivatives

Yang, Shuai; Peng, Hongxiang; Zhu, J.; Zhao, Chen; Xu, Hanhong

doi:10.1002/jhet.4476

Cited by 6 publications

(2 citation statements)

References 25 publications

(29 reference statements)

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“…This is evident in the compatibility of the gene expression data with molecular docking analysis (the lowest binding energy with ligands), which showed that the binding affinity between CHP and EBZ is high with SfGSTe10 and SfGSTe13 , and low with SfGSTs1 and SfGSTe2 . This result may be because the amino acids in the receptor are linked by double or triple bonds, and the docking binding affinity is high with lower binding energy [ 71 , 72 ]. Additionally, the type and position of amino acids in the active site of GSTs (the G-site and H-site) play important roles in insecticide binding affinity and catalytic functions [ 73 ].…”

Section: Discussionmentioning

confidence: 99%

Identification and Characterization of Glutathione S-transferase Genes in Spodoptera frugiperda (Lepidoptera: Noctuidae) under Insecticides Stress

Aioub

Hashem

El-Sappah

et al. 2023

Toxics

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Insect glutathione S-transferases (GSTs) serve critical roles in insecticides and other forms of xenobiotic chemical detoxification. The fall armyworm, Spodoptera frugiperda (J. E. Smith), is a major agricultural pest in several countries, especially Egypt. This is the first study to identify and characterize GST genes in S. frugiperda under insecticidal stress. The present work evaluated the toxicity of emamectin benzoate (EBZ) and chlorantraniliprole (CHP) against the third-instar larvae of S. frugiperda using the leaf disk method. The LC50 values of EBZ and CHP were 0.029 and 1.250 mg/L after 24 h of exposure. Moreover, we identified 31 GST genes, including 28 cytosolic and 3 microsomal SfGSTs from a transcriptome analysis and the genome data of S. frugiperda. Depending on the phylogenetic analysis, sfGSTs were divided into six classes (delta, epsilon, omega, sigma, theta, and microsomal). Furthermore, we investigated the mRNA levels of 28 GST genes using qRT-PCR under EBZ and CHP stress in the third-instar larvae of S. frugiperda. Interestingly, SfGSTe10 and SfGSTe13 stood out with the highest expression after the EBZ and CHP treatments. Finally, a molecular docking model was constructed between EBZ and CHP using the most upregulated genes (SfGSTe10 and SfGSTe13) and the least upregulated genes (SfGSTs1 and SfGSTe2) of S. frugiperda larvae. The molecular docking study showed EBZ and CHP have a high binding affinity with SfGSTe10, with docking energy values of −24.41 and −26.72 kcal/mol, respectively, and sfGSTe13, with docking energy values of −26.85 and −26.78 kcal/mol, respectively. Our findings are important for understanding the role of GSTs in S. frugiperda regarding detoxification processes for EBZ and CHP.

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Section: Discussionmentioning

confidence: 99%

Identification and Characterization of Glutathione S-transferase Genes in Spodoptera frugiperda (Lepidoptera: Noctuidae) under Insecticides Stress

Aioub

Hashem

El-Sappah

et al. 2023

Toxics

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show abstract

“…Insecticidal activity against Helicoverpa armigera . The soaking method was adopted ( Yang et al, 2022 ). After soaking a proper amount of corn leaves for 10 s, they were placed in a plastic Petri dish with filter paper and dried naturally in the shade.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and insecticidal activity of a novel series of flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits

Zhao

Tang²,

Huang³

et al. 2022

Front. Chem.

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To discover new potential insecticides to protect agricultural crops from damage, a series of novel flupyrimin derivatives containing an arylpyrazole core were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Bioassays indicated that the 31 compounds synthesized possessed excellent insecticidal activity against Plutella xylostella. Among these target compounds, the lethality of A3, B1-B6, D4, and D6 reached 100% at 400 μg/ml. Moreover, when the concentration dropped to 25 μg/ml, the insecticidal activities against the Plutella xylostella for compounds B2, B3, and B4 still reached more than 70%. The structure–activity relationship of the Plutella xylostella was discussed. The density functional theory analysis of flupyrimin and B4 was carried out to support the abovementioned structure–activity relationship. The possible binding modes between receptor and active groups in title compounds were also verified by docking simulation. These results provided new ideas for the development of these novel candidate insecticides in the future.

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The Docking and Physiological Characteristics as Detectors of Nanoparticle’s Role in Plant Responses to Biotic Stress

El-Abeid,

El-Tabakh,

Shehata

et al. 2024

Nanoparticles in Plant Biotic Stress Management

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Design, synthesis, insecticidal activities, and molecular docking of novel pyridylpyrazolo carboxylate derivatives

Cited by 6 publications

References 25 publications

Identification and Characterization of Glutathione S-transferase Genes in Spodoptera frugiperda (Lepidoptera: Noctuidae) under Insecticides Stress

Identification and Characterization of Glutathione S-transferase Genes in Spodoptera frugiperda (Lepidoptera: Noctuidae) under Insecticides Stress

Design, synthesis, and insecticidal activity of a novel series of flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits

The Docking and Physiological Characteristics as Detectors of Nanoparticle’s Role in Plant Responses to Biotic Stress

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