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Synthesis and Biological Evaluation of New Ozonides with Improved Plant Growth Regulatory Activity

Barbosa, L. C. A., Maltha, C. R. A., Cusati, R. C., Teixeira, R. R., Rodrigues, F. F., Silva, A. A., Drew, M. G. B. and Ismail, F. M. D. (2009) Synthesis and Biological Evaluation of New Ozonides with Improved Plant Growth Regulatory Activity. Journal of Agricultural and Food Chemistry, 57 (21). pp. 10107-10115. ISSN 0021-8561

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To link to this item DOI: 10.1021/jf902540z

Abstract/Summary

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-[4.4.1.1(2,5)]-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 x 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.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:10991
Uncontrolled Keywords:Herbicides, plant growth regulators, 1,2,4-trioxolanes, stable, ozonides, [4+3] cycloaddition, density functional theory, ANTIMALARIAL ACTION, PHYTOTOXIC ACTIVITY, NOSTOCLIDE ANALOGS, POLYBROMO, KETONES, CONCISE SYNTHESIS, OXYALLYL CATIONS, ARTEMISININ, DERIVATIVES, MODE, DRUG

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