title: Synthesis and biological evaluation of new ozonides with improved plant growth regulatory activity.
abstract: 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.
authors.affiliation: Department of Chemistry, ederal University of Vic-osa, Avenida P.H. Rolfs, CEP 36570-000, Vic-osa, MG, Brazil. lcab@ufv.br
authors.forename: Luiz C A
authors.initials: LC
authors.lastname: Barbosa
authors.forename: Célia R A
authors.initials: CR
authors.lastname: Maltha
authors.forename: Raphael C
authors.initials: RC
authors.lastname: Cusati
authors.forename: Róbson R
authors.initials: RR
authors.lastname: Teixeira
authors.forename: Filipe F
authors.initials: FF
authors.lastname: Rodrigues
authors.forename: Antônio A
authors.initials: AA
authors.lastname: Silva
authors.forename: Michael G B
authors.initials: MG
authors.lastname: Drew
authors.forename: Fyaz M D
authors.initials: FM
authors.lastname: Ismail
mesh_terms: D018553:Cucumis sativus / Q000187:drug effects / Q000254:growth & development*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045868:Sorghum / Q000187:drug effects / Q000254:growth & development*
chemical_list: C503429:1,2,4-trioxane; D006571:Heterocyclic Compounds