Solvothermal synthesis of novel phenylpyrazole Schiff base fluorescent insecticides fused extended conjugate units for enhancing bioactivities, photophysical and electrochemical properties

Chen, Lianqing; Wu, Zhongda; Du, Yanting; Huang, Yu-Feng; Jin, Shiwei

doi:10.1016/j.molstruc.2019.06.093

Cited by 5 publications

(2 citation statements)

References 22 publications

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“…In addition, the electron vibrational structure in the fluorescence spectra indicates that the emission of these molecules mainly comes from the π–π* conjugation system of the ester unit with the benzene ring, which further demonstrates the importance of π–π* electron transfer in the molecules. Thus, the analysis of fluorescence spectral data showed that PEs have excellent fluorescence properties in solution, and their unique fluorescence properties were utilized to achieve accurate detection of residues …”

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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“…And among them, vaniliprole ( VI ) (Figure 1) with Schiff base structure derived from 5-amino group was verified to be a kind of new insecticidal derivative, which is less harmful to the environment and user. Compounds containing an alkynyl group usually possess anti-tumor, anti-inflammatory, and anti-oxidation biological activities [18,19]. Series of alkynyl compounds such as propargite [20], oxadiargyl [21], and mepanipyrim [22] were applied as unique insecticides, fungicides, and herbicides, respectively.…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids Enhanced Alkynyl Schiff Bases Derivatives of Fipronil Synthesis and Their Cytotoxicity Studies

et al. 2019

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To obtain highly selective toxic derivatives of fipronil, a series of Schiff bases with an alkynyl group (3a–3k) were designed and synthesized from 4-ethynylbenzaldehyde (2) and 4-substituted 5-amino-N-arylpyrazole (1a–1k) via a nucleophilic addition elimination reaction in ionic liquids. Utilization of ionic liquids was demonstrated to endow the yield of each compound beyond 50%, which was enhanced over 1.5 times of the synthetic productive rates comparing the conventional method by which longer reactive time was consumed. The derivatives were characterized via nuclear magnetic resonance hydrogen spectroscopy (1H-NMR), carbon-13 nuclear magnetic resonance spectroscopy (13C-NMR), and electrospray ionization high resolution mass spectrometry (ESI-HRMS). The cytotoxicity of these derivatives on Trichoplusia ni (Hi-5) cell and Spodoptera litura cell (SL cell) was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) bioassays. The results indicated that several compounds had potential cytotoxicity on Hi-5 cell, especially a 4-ethyl substituted alkynyl Schiff base derivative (3f) that was demonstrated to possess high selective toxicity to the Hi-5 cell than the SL cell. In addition, 3f exhibited comparable toxic activity to commercial fipronil on a Hi-5 cell while a little toxic effect on the SL cell, which satisfied the expectation for selective toxicity screening.

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New prospects on solvothermal carbonisation assisted by organic solvents, ionic liquids and eutectic mixtures – A critical review

Mruthunjayappa

Kotrappanavar

Mondal

2022

Progress in Materials Science

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Solvothermal synthesis of novel phenylpyrazole Schiff base fluorescent insecticides fused extended conjugate units for enhancing bioactivities, photophysical and electrochemical properties

Cited by 5 publications

References 22 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

Ionic Liquids Enhanced Alkynyl Schiff Bases Derivatives of Fipronil Synthesis and Their Cytotoxicity Studies

New prospects on solvothermal carbonisation assisted by organic solvents, ionic liquids and eutectic mixtures – A critical review

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