Chiral Supramolecular Systems Based on β‐Cyclodextrin for Agricultural Applications: Differential Foliar Affinity, Biofilm Degradation, and Control Efficacy

While chiral pesticides have attracted considerable attention in agriculture, the potential of chirality‐dependent supramolecular materials remains largely untapped. Here, two chiral enantiomers, AQA‐10S and AQA‐10R are engineered, and encapsulated them within β ‐cyclodextrin ( β ‐CD) and cucurbit[7]uril (CB[7]) to fabricate the supramolecular assemblies AQA‐10S/R@ β ‐CD and AQA‐10S/R@CB[7]. Encapsulation with β ‐CD enhanced the in vitro attributes of the guest molecules, whereas CB[7] conferred minimal benefit. Specially, deposition of AQA‐10R@ β ‐CD on rice leaves increases by 112.58% relative to AQA‐10R, with an even greater enhancement of 123.87% observed on tomato foliage. Moreover, AQA‐10S/R@ β ‐CD exhibits enantioselective biofilm disruption and differential adhesion to plant surfaces. This latter property is exemplified by 85.55%/71.64% increase in deposition of AQA‐10R@ β ‐CD relative to its S ‐configured counterpart. Despite comparable in vitro antimicrobial potency, distinct chiral‐dependent efficacy emerged in planta, with AQA‐10R@ β ‐CD displaying superior protective effects. At 200 µg mL −1 , AQA‐10R@ β ‐CD conferred protective efficiencies of 63.92% against bacterial leaf streak and 66.35% against tomato bacterial canker, outperforming both the commercial agent (45.27%/43.04%) and the free guest molecules (51.71%/52.43%). By integrating plant bioavailability into the consideration, beyond conventional focus on chirality‐driven activity, this work offers a supramolecular strategy for the development of environmentally benign, broad‐spectrum antimicrobial agents, providing a conceptual framework for next‐generation green agrochemicals.