title: Design, synthesis, and analysis of the quantitative structure-activity relationships of 4-phenyl-acyl-substituted 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione derivatives.
abstract: 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 (1)H NMR (or (13)C 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.
authors.affiliation: Ministry of Agriculture Key Laboratory of Molecular Biology of Crop Pathogens and Insects, Institute of Pesticide and Environment Toxicology, Zhejiang University, Hangzhou 310029, China. jinhaozhao@zju.edu.cn
authors.forename: Jinhao
authors.initials: J
authors.lastname: Zhao
authors.forename: Jiangong
authors.initials: J
authors.lastname: Zhang
authors.forename: Bingrong
authors.initials: B
authors.lastname: Xu
authors.forename: Zongcheng
authors.initials: Z
authors.lastname: Wang
authors.forename: Jingli
authors.initials: J
authors.lastname: Cheng
authors.forename: Guonian
authors.initials: G
authors.lastname: Zhu
mesh_terms: D056810:Acaricides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D001042:Aphids / Q000187:drug effects; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D040102:Tetranychidae / Q000187:drug effects
chemical_list: D056810:Acaricides; D007306:Insecticides