Design, synthesis, and antifungal activities of novel sulfoximine derivatives for plant protection.

BACKGROUND

Fungicides play a significant role in the integrated management of plant pathogens. However, the irrational application of fungicides with similar structures has led to development of cross-resistance, therefore there is a need to seek novel fungicides with new structures.

RESULTS

Twenty-eight novel sulfoximine derivatives incorporating nitroguanidine moieties were designed, synthesized, and evaluated as antifungal agents. The bioassay results indicated that most of the synthesized compounds displayed excellent fungicidal activities against Sclerotinia sclerotiorum, Rhizoctonia solani, Fusarium graminearum, and Pyricularia grisea. Among these, compounds 6c4 , 6c5 , and 6c6 exhibited remarkable fungicidal activities against P. grisea, with EC50 values of 1.28, 1.17, and 1.68 μg mL-1 , respectively. In addition, compound 6c2 displayed the most potent activity against S. sclerotiorum (EC50  = 3.64 μg mL-1 ). Further in vivo fungicidal activity screening against S. sclerotiorum demonstrated that the protective and curative effects of compound 6c2 were 98.1% and 91.3% at 25 μg mL-1 , respectively, comparable to that of boscalid (94.4%, 89.6%). The preliminary mechanism study found that the hyphae of S. sclerotiorum treated with compound 6c2 was abnormal with mycelial collapse and membrane permeability increase. The present findings can help to develop new fungicides for crop protection.

CONCLUSION

Novel sulfoximine derivatives containing nitroguanidine possess potential antifungal activity, and the unique structure may offer an alternative option for fungicide development in the future. © 2022 Society of Chemical Industry.