Lead optimization and insecticidal activity of analogues of daphneolone isolated from Stellera chamaejasme L.
Starting from the chemical structure of the botanical aphicides 1,5-diphenyl-1-pentanone and 1,5-diphenyl-2-penten-1-one, extracted from Stellera chamaejasme L., the authors designed and synthesized a series of novel compounds following the concept of bioisosterism. Their structures were established on the basis of (1)H NMR and GC-MS spectra, and the insecticidal activities of the compounds were evaluated against Aphis gossypii Glover. The results demonstrated that the substitution of a heterocycle for the phenyl ring was favourable. Thus, further modification of compound 2n, containing a furan ring, which showed excellent activity (LC(50) = 0.85 g L(-1)), is of some promise.
Chen
Lin
L
Key Laboratory of Bio-Resource and Eco-environment, Ministry of Education, College of Life Sciences, Sichuan University, Chengdu 610064, China.
Wang
Xinliang
X
Lu
Tao
T
Hou
Taiping
T
D000818:Animals; D001042:Aphids; D008401:Gas Chromatography-Mass Spectrometry; D007306:Insecticides / Q000138:chemical synthesis*; D007854:Lead / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010422:Pentanones / Q000737:chemistry* / Q000302:isolation & purification; D013329:Structure-Activity Relationship; D029645:Thymelaeaceae / Q000737:chemistry*
C433344:1,5-diphenyl-1-pentanone; C433345:1,5-diphenyl-2-penten-1-one; D007306:Insecticides; D010422:Pentanones; D007854:Lead