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The search for sustainable alternatives to synthetic herbicides for weed control, has led the scientific community to an increased interest for plant allelopathic mechanisms. The utilization of plant extracts as possible bioherbicides represents an important solution. In the present study, laboratory experiments were carried out to investigate, for the first time, the differences in the allelopathic activity of the three Cynara cardunculus L. botanical varieties (globe artichoke, cultivated and wild cardoon) leaf aqueous extracts on the seedling growth of Amaranthus retroflexus L. and Portulaca oleracea L. In addition, the autoallelopathic effect on wild cardoon growth and the qualitative profile of the aqueous extract through HPLC analysis were evaluated. Overall, the allelopathic effects were both genotype- and weed species-dependent. Wild cardoon showed the highest allelopathic potential (–23.4%), followed by cultivated cardoon and globe artichoke, and P. oleracea was the most sensitive target species (–32%). Besides, root system length was the most affected parameter (–32.6%). The autoallelopathic effect of wild cardoon extract was also demonstrated on root system length, hypocotyl and epicotyl length and total dry weight. C. cardunculus leaf aqueous extract was characterised by 5 sesquiterpene lactones, 2 caffeoylquinic acids, 6 flavones and 1 lignan. From the HPLC analysis we found that apigenin and luteolin 7-O-glucoronide were detected only in wild cardoon, apigenin 7-O-glucoside was typic of globe artichoke, and 11,13-dihydro-desacylcynaropicrin and 11,13-dihydroxi-8-desoxygrosheimin were characteristics of cultivated cardoon.