Development of RS-pyrisoxazole for reduction of pesticide inputs: A new insight from systemic evaluation of pyrisoxazole at the stereoisomeric level

Pyrisoxazole is a chiral fungicide that is routinely applied to agricultural plant protection, but the potential environmental risk may be under- or over-estimated because the risk induced by stereoisomers have never been evaluated individually. Thus, we carried out a systemic evaluation of pyrisoxazole at the stereoisomeric level, including absolute configuration, stereoselective bioactivity, acute toxicity, and stereoselective dissipation behavior. There were 99.0-3545.3 fold difference in bioactivity toward six target pathogens (e.g., Alternaria solani) and 1.3-4.0 times difference in toxicity against aquatic organisms (Selenastrum capricornutum and Daphnia magna) between the best and worst stereoisomer. There appeared to be no significant stereoselective dissipation in all three kinds of soil under aerobic and anaerobic conditions. Stereoselective dissipation in buffer solution and river water only observed between diastereomers rather than between enantiomers. In addition, photolysis played a central role in the dissipation of pyrisoxazole in river water. RS-pyrisoxazole was 2.2- to 6.9-times more bioactive and 1.2- to 2.1-times more toxic than Rac-pyrisoxazole, and what is more, RS-pyrisoxazole degraded faster than other stereoisomers in river water. The result implicated that developing pure RS-pyrisoxazole as commercial product could reduce the input of inactive isomer on the basis of guaranteeing the efficacy against the target pathogens.

Absolute configuration; Acute toxicity; Bioactivity; Stereoselective dissipation.