新型含苯基取代嘧啶基磺酰脲衍生物的设计、 合成及生物活性

将苯基引入到嘧啶环的4位, 设计、 合成了2个系列共24个结构新颖的磺酰脲类衍生物, 并对其生物活性进行了研究. 抑菌实验结果表明, 目标化合物对苹果轮纹病菌和小麦纹枯病菌表现出优异的抑制率, 其中化合物9f对5种病菌的抑制率均超过65%. 进一步研究发现, 化合物9f对苹果轮纹病菌的EC₅₀值为8.63 mg/L, 略高于对照药百菌清(7.33 mg/L); 化合物8k和9k对小麦纹枯病菌的EC₅₀值分别为5.48和6.09 mg/L, 与百菌清(4.26 mg/L)接近. 同时, 盆栽法除草测试结果表明, 在75 g/ha剂量下, 化合物8d和9d对油菜具有较好的芽前除草活性, 分别为86%和73%; 化合物9h对反枝苋的土壤处理抑制活性为100%, 优于对照药氯磺隆(96%).

Design,Synthesis and Biological Activity of Novel Sulfonylurea Derivatives Containing Phenyl-substituted Pyrimidine Moiety†

Acetolactate synthase(ALS) has been regarded as an attractive target for fungicide and herbicide discovery. Furthermore, sulfonylurea(SU) as one of the most active ALS inhibitors were used as herbicides in crops protect. In order to discuss the multi-biological activity of SU, two series of novel SU derivatives containing phenyl-substituted pyrimidine moiety were designed, synthesized and their antifungal activity and herbicidal activity were evaluated. The bioassay results indicated that some title compounds showed excellent antifungal activity against Physalospora piricola and Rhizoctonia cerealis in vitro at the dosage of 50 mg/L. Particularly, compound 9f exhibited more than 65% inhibitory activity against five phytopathogens. On the basis of advanced screening test, the EC₅₀ value of compound 8f against P. piricola was 8.63 mg/L, which was a little higher than Chlorothalonil(EC₅₀=7.33 mg/L), the EC₅₀ value of compounds 8k(5.48 mg/L) and 9k(6.09 mg/L) against R. cerealis were similar to Chlorothalonil(EC₅₀=4.26 mg/L). In addtion, the title compounds showed favorable pre-emergence treatment herbicidal activity against Brassica napus and Amaranthus retroflexus at the dosage of 75 g/ha. For example, compounds 8d and 9d showed 86% and 73% inhibition activity respectively against Brassica napus; compound 9h exhibited 100% herbicidal activity against Amaranthus retroflexus, which was better than that of Chlorsulfuron(96%). The results provided useful information for designing new SU with highly fungicidal activity and herbicidal activity.