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一些新型含氮杂环衍生物作为家蝇杀虫剂和光敏剂的生态可持续合成及其潜在效率

Eco-sustainable Synthesis and Potential Efficiency of Some Novel N-containing Heterocyclic Derivatives as Insecticidal and Photosensitizing Agents Against Musca domestica L.

作者信息

Hassan A M A, Abubshait Samar A, Abdel-Haleem Doaa R, El-Naggar Abeer M, Hassaballah Aya I

机构信息

Department of Chemistry, Faculty of Science, Ain Shams University, 11566, Abbassia, Cairo, Egypt.

Department of Chemistry, Collage of Science, Imam Abdulrahman Bin Faisal University, P.O. Box 1982, 32441, Dammam, Saudi Arabia.

出版信息

Chem Biodivers. 2024 Dec;21(12):e202401650. doi: 10.1002/cbdv.202401650. Epub 2024 Oct 28.

DOI:10.1002/cbdv.202401650
PMID:39231387
Abstract

The rising application of conventional synthetic insecticides develops resistant populations of houseflies; therefore, using new chemical agents with different modes of action is essential to overcome this problem. The mechanical grinding technique was used as a green method, to synthesize the tested compounds because it is a more facile work-up and high-yield economy, simplicity and solvent-free than conventional thermal technique. Various methods were employed to synthesize new heterocycles containing anthracene (a photosensitizing agent) from chalcone 3, a building block material such as the preparation of the pyrazole derivatives 4-7, isoxazole derivative 8, pyrimidines 9-11, and oxirane derivative 12. The novel synthesized compounds were analyzed by FT-IR, H-NMR, C-NMR spectra, and elemental analysis. Herein, the toxicity of the anthracene derivatives was assessed against Musca domestica larvae and adults in different conditions to demonstrate the effect of various inserted moieties on the efficiency of tested compounds. Furthermore, the influence of sunlight on the toxicity of anthracene was studied in dark and sunlight tests against adult houseflies. Moreover, these compounds diminished the total protein and lipids contents while significantly influencing the antioxidant enzymes activities of M. domestica adults. Structure-activity relationships demonstrated the role of each moiety on the toxicity of compounds.

摘要

传统合成杀虫剂的应用日益广泛,导致家蝇产生了抗性种群;因此,使用具有不同作用方式的新型化学药剂对于解决这一问题至关重要。机械研磨技术作为一种绿色方法,用于合成受试化合物,因为与传统热技术相比,它后处理更简便、产率更高、经济、简单且无溶剂。采用了各种方法从查尔酮3合成含蒽(一种光敏剂)的新型杂环化合物,蒽是一种构建材料,如制备吡唑衍生物4 - 7、异恶唑衍生物8、嘧啶9 - 11和环氧乙烷衍生物12。通过傅里叶变换红外光谱(FT - IR)、氢核磁共振(H - NMR)、碳核磁共振(C - NMR)光谱和元素分析对新合成的化合物进行了分析。在此,评估了蒽衍生物在不同条件下对家蝇幼虫和成虫的毒性,以证明各种插入基团对受试化合物效率的影响。此外,在黑暗和光照条件下对成年家蝇进行测试,研究了阳光对蒽毒性的影响。此外,这些化合物降低了家蝇成虫的总蛋白和脂质含量,同时显著影响了其抗氧化酶活性。构效关系表明了每个基团对化合物毒性的作用。

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