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Sesquiterpene lactones (SLs) are compounds that are highly produced in <i>Cynara cardunculus</i> leaves, known for their phytotoxic activity. This study aims to assess SL-enriched fractions’ (cynaropicrin, aguerin B, and grosheimin) phytotoxic potentials and putative modes of action, compared to an initial extract, using two approaches: first, against a panel of nine weed species in pre-emergence, and then on <i>Portulaca oleracea</i> L.’s post-emergency stage. The SL-enriched fractions demonstrated greater phytotoxic activity when compared with the <i>C. cardunculus</i> leaf initial extract. The SL-enriched fractions had higher activity at root growth inhibition over the panel tested, doubling the activity in five of them at 800 ppm. Regarding the post-emergence bioassay, the SL-enriched fractions had a higher influence on the plants’ growth inhibition (67% at 800 ppm). The SL-effects on the plants’ metabolisms were evidenced. The total chlorophyll content was reduced by 65% at 800 ppm. Oxidative stress induction was observed because of the enhancement in MDA levels at 800 ppm compared to control (52%) and the decrease in SOD-specific activity from 4.20 U/mg protein (400 ppm) to 1.74 U/mg protein (800 ppm). The phytotoxic effects of the SL-enriched fractions suggest that they could be used for a future bioherbicide development.