Host-guest complexation of phthalimide-derived strigolactone mimics with cyclodextrins. Application in agriculture against parasitic weeds

Parasitic weeds are noxious plants that damage crops of economic relevance, especially in Mediterranean and African countries. The strategy of suicidal germination was proposed to deal with this plague by using seed germination inducers that work as a pre-emergence herbicide and reduce the parasitic seed load before sowing. N-substituted phthalimides with a furanone ring were found to be efficient to induce germination of Phelipanche ramosa and Orobanche cumana, two of the most problematic parasitic weeds for crops. However, the solubility in water of these compounds is low. A strategy to enhance their aqueous solubility is the synthesis of host-guest complexes with cyclodextrins. Three bioactive phthalimide-lactones (PL01, PL04, and PL07) were selected and studied to form complexes of increased water solubility with α-, β-, HP-β-, and γ-cyclodextrin. The complexes obtained by the coprecipitation method, with increased aqueous solubility (up to 3.8 times), were studied for their bioactivity, showing a similar or slightly higher bioactivity compared to the free phthalimide-lactones, even without the addition of organic solvents. A theoretical study using semiempirical calculations of molecular models including the solvation system confirmed the physicochemical empirical results. These results demonstrated that cyclodextrins can be used to improve the physicochemical and biological properties of parasitic seed germination inducers.

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