One pot solvothermal synthesis of novel fluorescent phloem-mobile phenylpyrazole amide pesticides fused olefin moieties to enhance insecticidal bioactivities and photodegradation properties

Wu, Zhongda; Du, Yanting; Zhou, Quan; Chen, Lianqing

doi:10.1016/j.pestbp.2019.10.003

Cited by 7 publications

(3 citation statements)

References 35 publications

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“…Compared to the traditional oil bath heating method, the solvent-thermal method significantly shortened the reaction time and increased the yield. Due to the closed high-temperature and high-pressure reaction environment, the interactions between reactant molecules were enhanced, greatly accelerating the reaction rate . Moreover, in the solvent-thermal method, the solubility of reactants in the solvent increased, reducing the loss of quality and improving the yield.…”

Section: Resultsmentioning

confidence: 99%

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Liu,

Wu,

et al. 2024

J. Agric. Food Chem.

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In the pursuit of novel insecticides with high activity and a unique mode of action on the GABA receptor, a series of phenylpyrazole esterified derivatives (PEs) were synthesized using an improved Pinner reaction with high selectivity. Lewis acid catalysis was employed in a one-step solvent-thermal method to convert the cyano group of fipronil into an ester unit. FeCl3 was found to exhibit the highest selectivity for PEs synthesis, yielding PEs at 96.4%, with the byproduct being phenylpyrazole amide (PE 0 ) at 2.1%. Initial biological assays indicated superior insecticidal activity of the target compounds against Plutella xylostella and Mythimna separata compared to fipronil. Particularly, the smaller and shorter ester units, PE 3 , PE 5 , and PE 8 , demonstrated 2–2.5 times higher insecticidal activity against P. xylostella than fipronil. The higher activity of ester units compared to amide and acylhydrazone units can be attributed to the enhanced lipid solubility of PEs. Additionally, it may be due to the impact of PEs on the neurotransmitter nACh or the coordination of calcium and chloride ions with the ester’s −CO and −O– bonds, blocking the chloride ion channel. Hydrophobic parameters were confirmed by reversed-phase high-performance liquid chromatography (HPLC), indicating the enhanced lipophilicity conferred by the ester units of PEs. Molecular docking and CoMFA analysis preliminarily validated the strong interactions and structure–activity relationships between PEs and the GABA receptor and nACh receptor in P. xylostella. Furthermore, under simulated natural sunlight, PEs exhibited photodegradation capabilities, transforming back into fipronil parent fragments and enhancing their insecticidal activity. Moreover, PEs displayed excellent fluorescent properties, enabling self-detection of residues. These research findings provide new insights and directions for the development of efficient pesticides, with potential wide applications in the fields of medicine and biosensors.

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Section: Resultsmentioning

confidence: 99%

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Liu,

Wu,

et al. 2024

J. Agric. Food Chem.

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“…The cleavage of coordination bonds in APSn M further converted it into APSn . It has been reported in the literature that derivatives modified on the 5-amino group of fipronil will further convert into fipronil in plants, remaining active for a reasonable period of time …”

Section: Resultsmentioning

confidence: 99%

“…It has been reported in the literature that derivatives modified on the 5-amino group of fipronil will further convert into fipronil in plants, 49 remaining active for a reasonable period of time. 50 To further explore the optical performance of the ligandgated ion channel, during simulation of natural light (λ ≥ 290 nm), APS3 Na was subjected to a photostability experiment lasting 10 h. Absorbance and fluorescence intensity were recorded per hour.…”

Section: Photodegradation Properties Of Fluorescent Ligand-gated Ion ...mentioning

confidence: 99%

Design and One-Pot Ultrasound Synthesis of Inorganic Base-Promoted Fluorescent Ligand-Gated Ion Channel Fused Arylpyrazole Sulfonamide Skeletons to Enhance Phloem Mobility and Insecticidal Activity as GABA and nACh Receptors Inhibitors

Xu,

Wu,

Wan

et al. 2023

J. Agric. Food Chem.

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Ligand-gated ion channels are essential in living organisms, and sulfonamides have antibacterial effects and can be readily coordinated with metal ions with good biological activity. A series of fluorescent ligand-gated ion channel fused arylpyrazole sulfonamide skeletons (APSn M ) were synthesized based on a one-pot ultrasound strategy promoted by an inorganic base. APSn M had a high fluorescence quantum yield and a large Stokes shift in ethanol solvent. The ligand bonded ions took on a different color from the ligand and can be used as a probe to detect their own residue on plant surfaces. Their hydrophobic parameters and the fluorescence distribution in Chinese cabbage leaves indicated that APSn M significantly increased the phloem mobility of the plant. The insecticidal activity of APS3 Na was higher (LC 50 = 7.2423 μg/mL) than that of fipronil (15.2312 μg/mL) against Plutella xylostella, and the mechanism of high insecticidal activity of APS3 Na was simulated by molecular docking, which confirmed its strong interactions with the GABA and nACh receptors of Plutella xylostella. Analysis of the crystal structure of these ligand-gated ion channels further confirmed the consistency of their structure and biological activity.

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Synthesis, antiproliferative activities, and DNA binding of coumarin‐3‐formamido derivatives

Shi

Chen

et al. 2020

Archiv der Pharmazie

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Ten coumarin‐3‐formamido derivatives, N‐benzyl‐coumarin‐3‐carboxamide (2), N‐fluorobenzyl‐coumarin‐3‐carboxamide (3–5), N‐methoxybenzyl‐coumarin‐3‐carboxamide (6–8), N‐((1‐methyl‐1H‐imidazol‐5‐yl)methyl)‐coumarin‐3‐carboxamide (9), N‐(thiophen‐2‐ylmethyl)‐coumarin‐3‐carboxamide (10), and N‐(furan‐2‐ylmethyl)‐coumarin‐3‐carboxamide (11), were synthesized and characterized. Compound 5 crystallizes in a monoclinic system P21/c space group with four chemical formulas in a unit cell; molecules of compound 5 are self‐assembled into a two‐dimensional supramolecular structure by intermolecular hydrogen bonds and C⋯C π stacking. The potential anticancer effects of these compounds on HeLa (cervical carcinoma), MCF‐7 (breast), A549 (lung), HepG2 (liver), and human umbilical vein (HUVEC) cells were examined. Compared with compounds 1–8 and 10–11, compound 9 exhibits potent in vitro cytotoxicity against HeLa cells and lower cytotoxicity against normal cells. Therefore, further in‐depth investigations of compound 9 were performed. Absorption titration experiments and fluorescence spectroscopy studies suggested that compound 9 binds to DNA through the intercalation mode.

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One pot solvothermal synthesis of novel fluorescent phloem-mobile phenylpyrazole amide pesticides fused olefin moieties to enhance insecticidal bioactivities and photodegradation properties

Cited by 7 publications

References 35 publications

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Design and One-Pot Ultrasound Synthesis of Inorganic Base-Promoted Fluorescent Ligand-Gated Ion Channel Fused Arylpyrazole Sulfonamide Skeletons to Enhance Phloem Mobility and Insecticidal Activity as GABA and nACh Receptors Inhibitors

Synthesis, antiproliferative activities, and DNA binding of coumarin‐3‐formamido derivatives

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