Testing Differently Substituted Quinoxaline‐2,3‐Dithiolate Ligands in <i>Z</i>‐Stereoretentive Olefin Metathesis Leading to Pheromone of Rice Yellow Stem Borer (<i>Scirpophaga incertulas</i>)

ABSTRACT Stereoselective olefin metathesis offers access to geometrically well‐defined C–C double bonds and is considered a promising new method for transforming plant oils to valuable chemicals. A set of Z ‐stereoretentive catalysts bearing quinoxaline‐2,3‐dithiolate ligands functionalized with halogens, electron‐withdrawing (EWG), electron‐donating (EDG), and π‐altered were obtained and characterized. New catalysts were tested in a model Z ‐stereoselective cross‐metathesis (CM) and in the synthesis of a pheromone of rice yellow stem borer ( Scirpophaga incertulas ). Although none of the new catalysts surpassed the parent catalyst Ru5a —featuring non‐substituted quinoxaline‐2,3‐dithiolate ligand—the ester‐substituted complex Ru5h offered a similarly high level of Z ‐selectivity (&gt;95:5) and productivity, whereas the carboxylic ester function can open perspectives for future immobilization or polar‐tagging. Practical Applications : Decreasing availability of fossil organic feedstock and current policies of the European Union drive scientists to look for alternative sustainable sources of fine chemicals. In this context, Z ‐stereoselective olefin metathesis offers preferential access to geometrically well‐defined C–C double bonds and is considered a new promising method for transforming plant oils to valuable chemicals. One of them is sex pheromones of various insects—biodegradable and non‐toxic chemical substances—used in small amounts to lure insects into pheromone traps. In the present work, a female sex pheromone of rice yellow stem borer ( Scirpophaga incertulas ) was obtained in high yield and selectivity, showing a possible application of the newly obtained Z ‐stereoretentive catalysts in the field of modern and environmentally conscious farming.