Sesquiterpene lactones with potential use as natural herbicide models. 2. Guaianolides

A structure-activity study to evaluate the effect of 17 guaianolide sesquit erpene lactones (in a range of 100-0.001 muM) on the growth and germination of several mono- and dicotyledon target species is accomplished. Results a re compared with those obtained in the same bioassay with an internal stand ard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. Specific conditions f or the selective mono- or polyhydroxylation of guaianolides using the SeO2/ tert-butyl hydroperoxide system are presented and discussed. The high regio - and stereoselectivities of the reaction are explained through the specifi c structural requirements of the bulky first adduct formed during the ene r eaction. These compounds appear to have deeper effects on the growth of eit her monocots or dicots than the previously tested germacranolides. Otherwis e, the lactone group seems to be necessary for the activity, though it does not necessarily need to be unsaturated. However, the presence of a second and easily accessible unsaturated carbonyl system greatly enhances the inhi bitory activity. Lipophilicity and the stereochemistry of the possible anch oring sites are also crucial factors for the activity. Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead com pounds.