State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Syngenta Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK.
Molecules. 2022 Feb 23;27(5):1486. doi: 10.3390/molecules27051486.
Sulfonylurea herbicides are widely used as acetolactate synthase (ALS) inhibitors due to their super-efficient activity. However, some sulfonylurea herbicides show toxicity under crop rotation due to their long degradation time, for example, chlorsulfuron. Our research goal is to obtain chlorsulfuron-derived herbicides with controllable degradation time, good crop safety and high herbicidal activities. Based on our previously reported results in acidic soil, we studied the degradation behaviors of 5-dialkylamino-substituted chlorsulfuron derivatives (-) in alkaline soil (pH 8.39). The experimental data indicate that addition of the 5-dialkylamino groups on the benzene ring of chlorsulfuron greatly accelerated degradation in alkaline soil. These chlorsulfuron derivatives degrade 10.8 to 51.8 times faster than chlorsulfuron and exhibit excellent crop safety on wheat and corn (through pre-emergence treatment). With a comprehensive consideration of structures, bioassay activities, soil degradation and crop safety, it could be concluded that 5-dialkylamino-substituted chlorsulfuron derivatives are potential green sulfonylurea herbicides for pre-emergence treatment on both wheat and corn. The study also provides valuable information for the discovery of new sulfonylurea herbicides for crop rotation.
磺酰脲类除草剂由于其超高的活性，被广泛用作乙酰乳酸合成酶（ALS）抑制剂。然而，由于其降解时间较长，一些磺酰脲类除草剂在轮作作物中表现出毒性，例如氯磺隆。我们的研究目标是获得具有可控降解时间、良好作物安全性和高除草活性的氯磺隆衍生除草剂。基于我们之前在酸性土壤中报告的结果，我们研究了 5-二烷基氨基取代的氯磺隆衍生物（-）在碱性土壤（pH 8.39）中的降解行为。实验数据表明，在氯磺隆苯环上添加 5-二烷基氨基基团极大地加速了碱性土壤中的降解。这些氯磺隆衍生物在碱性土壤中的降解速度比氯磺隆快 10.8 到 51.8 倍，对小麦和玉米（通过芽前处理）表现出优异的作物安全性。综合考虑结构、生物测定活性、土壤降解和作物安全性，可以得出结论，5-二烷基氨基取代的氯磺隆衍生物是小麦和玉米芽前处理的潜在绿色磺酰脲类除草剂。该研究还为发现用于轮作的新磺酰脲类除草剂提供了有价值的信息。
