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Synthesis and Biological Evaluation of New Ozonides with Improved Plant Growth Regulatory Activity
journal contributionposted on 2009-11-11, 00:00 authored by Luiz C. A. Barbosa, Célia R. A. Maltha, Raphael C. Cusati, Róbson R. Teixeira, Filipe F. Rodrigues, Antônio A. Silva, Michael G. B. Drew, Fyaz M. D. Ismail
The iron oxyallyl carbocation generated from 2,7-dibromocycloheptanone was induced to undergo [4 + 3] cycloaddition reactions with various furans, affording a series of 12-oxatricyclo-[18.104.22.168,5]-dodec-3-en-11-one adducts. Similar methodology was used to prepare two additional cycloadducts using menthofuran and two homologous aliphatic dibromoketones. Dipolar cycloaddition of ozone to the adducts afforded the corresponding secondary ozonides (i.e., 1,2,4-trioxolanes) in variable yields. Ozonides were investigated by quantum mechanics at the B3LYP/6-31+G* level to study structural features including close contacts which may be responsible for enhancing ozonide stability. The effect of these ozonides and their corresponding precursor cycloadducts upon radicle growth of both Sorghum bicolor and Cucumis sativus was evaluated at 5.0 × 10−4 mol L−1. The most active cycloadducts and ozonides were also evaluated against the weed species Ipomoea grandifolia and Brachiaria decumbens, and the results are discussed. Compared to ozonides previously synthesized in our laboratory, the new ozonides described herein present improved plant growth regulatory activity.
Biological EvaluationCucumis sativusBrachiaria decumbensradicle growthozonide stabilityDipolar cycloadditionprecursor cycloadductsquantum mechanicsplant growthaliphatic dibromoketonesSorghum bicolorNew Ozonidesweed species Ipomoea grandifoliaB 3LYP levelSimilar methodologyPlant Growth Regulatory ActivityThe iron oxyallyl carbocation