A series of 4-phenyl-acyl-substituted 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione derivatives were designed and synthesized, and their structures were characterized using ¹H NMR (or ¹³C NMR), mass spectrometry, and elemental analysis. The bioactivities of the new compounds were evaluated. These compounds exhibited good inhibition activities against bean aphids (Aphis fabae) and carmine spider mite (Tetranychus cinnabarinus), and 4-phenyl acyl esters showed stronger bioactivity than 4-arylesterases and alkyl esters. The results showed that compound 8-I-e, which contains a para-methoxy group on the phenyl acyl, and compound 8-I-m, which contains a para-trifluoromethyl group on the phenyl acyl, displayed potent insecticidal activity against A. fabae and T. cinnabarinus respectively. The insecticidal activity showed a clear structure–activity relationship, confirming the importance of the flexible bridge. The DFT/B3LYP/6-31(d) level method was used to calculate molecular geometries and electronic descriptors. These factors included total energy, charge distribution, and the linear orbital level of the title compounds. Quantitative structure–activity relationship studies were performed on these compounds using quantum-chemical and physicochemical parameters as independent variables and insecticidal activity as a dependent variable. Insecticidal activity was most closely correlated (r > 0.8) with quantum chemical and physicochemical parameters.

中文翻译：

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设计，合成和分析4-苯基-酰基取代的3-（2,5-二甲基苯基）-4-羟基-1-氮杂[4.5] dec-3-ene-2,8的定量构效关系-二酮衍生物

设计合成了一系列4-苯基-酰基取代的3-（2,5-二甲基苯基）-4-羟基-1-氮杂[4.5]癸-3-烯-2,8-二酮衍生物，并对其结构进行了合成使用¹ H NMR（或¹³ C NMR），质谱和元素分析对化合物进行表征。评价了新化合物的生物活性。这些化合物对豆蚜（Aphis fabae）和胭脂红蜘蛛（Tetranychus cinnabarinus）显示出良好的抑制活性，并且4-苯基酰基酯的生物活性强于4-芳基酯酶和烷基酯。结果表明，化合物8-Ie和苯基8-Im化合物在苯基酰基上均含有对甲氧基。，在苯基酰基上含有对三氟甲基，分别显示出对农杆菌和朱砂丁香的强效杀虫活性。杀虫活性显示出清晰的结构-活性关系，证实了柔性桥的重要性。DFT / B3LYP / 6-31（d）级方法用于计算分子几何结构和电子描述符。这些因素包括总能量，电荷分布和标题化合物的线性轨道能级。使用量子化学和物理化学参数作为自变量，而杀虫活性作为因变量，对这些化合物进行了定量的构效关系研究。杀虫活性是最密切相关的（r > 0.8），并具有量子化学和物理化学参数。