A total of 32 novel sulfoximines bearing cyanoguanidine and nitroguanidine moieties were designed and synthesized by a rational molecule design strategy. The bioactivities of the title compounds were evaluated and the results revealed that some of the target compounds possessed excellent antifungal activities against six agricultural fungi, including Sclerotinia sclerotiorum, Fusarium graminearum, Phytophthora capsici, Botrytis cinerea, Rhizoctonia solani, and Pyricularia grisea. Among them, compounds 8e₁ and 8e₄ exhibited significant efficacy against P. grisea with EC₅₀ values of 2.72 and 2.98 μg/mL, respectively, which were much higher than that of commercial fungicides boscalid (47.95 μg/mL). Interestingly, in vivo assays determined compound 8e₁ possessed outstanding activity against S. sclerotiorum with protective and curative effectiveness of 98 and 95.6% at 50 μg/mL, which were comparable to those of boscalid (93.2, 91.9%). The further preliminary mechanism investigation disclosed that compound 8e₁ could damage the structure of the cell membrane of S. sclerotiorum, increase its permeability, and suppress its growth. Overall, the findings enhanced that these novel sulfoximine derivatives could be potential lead compounds for the development of new fungicides.

中文翻译：

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含有氰基胍和硝基胍部分的新型亚磺酰亚胺衍生物：设计、合成和生物活性


通过合理的分子设计策略，设计并合成了总共32种带有氰基胍和硝基胍部分的新型亚砜亚胺。对标题化合物的生物活性进行了评价，结果表明，部分目标化合物对核盘菌、禾谷镰刀菌、辣椒疫霉、灰葡萄孢、立枯丝核菌和稻瘟病菌等六种农业真菌具有优异的抗真菌活性。其中，化合物8e ₁ 和8e ₄ 对稻瘟病菌表现出显着的防治效果，EC ₅₀ 值分别为2.72和2.98μg/mL，远高于市售杀菌剂啶酰菌胺（47.95 μg/mL）。有趣的是，体内试验表明化合物8e ₁ 对核盘菌具有出色的活性，在50 μg/mL浓度下的保护和治疗效果分别为98%和95.6%，与啶酰菌胺（93.2%、91.9%）相当。 ）。进一步的初步机制研究表明，化合物8e ₁ 能够破坏核盘菌细胞膜的结构，增加其通透性，抑制其生长。总体而言，研究结果表明这些新型亚砜亚胺衍生物可能成为开发新型杀菌剂的潜在先导化合物。