Wang Lei, Ma Yi, Liu Xing-Hai, Li Yong-Hong, Song Hai-Bin, Li Zheng-Ming
The Research Institute of Elemento-Organic Chemistry, State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center(Tianjin), Nankai University, Tianjin, China.
Chem Biol Drug Des. 2009 Jun;73(6):674-81. doi: 10.1111/j.1747-0285.2009.00819.x.
A series of novel triazolinones were synthesized and their structures were characterized by (1)H NMR, elemental analysis and single-crystal X-ray diffraction analysis. The herbicidal activities were evaluated against Echinochloa crusgalli (L.) Beauv., Digitaria adscendens, Brassica napus and Amaranthus retroflexus. The herbicidal activity data indicated that the title compounds had higher activities with substituted benzyl group moieties than with other groups such as sulfonyl, alkyl, etc. To further investigate the structure-activity relationship, comparative molecular field analysis was performed on the basis of herbicidal activity data. Both the steric and electronic field distributions of comparative molecular field analysis are in good agreement in this work. The results showed that a bulky and electronegative group around the ortho- or para-positions of the benzene ring would possibly lead to higher activity. Based on the comparative molecular field analysis, compound I-23 was designed and synthesized, which display as good herbicidal activities as the commercial herbicide, carfentrazone-ethyl. The activity against Digitaria adscendens is 66.1% under pre-emergence at 300 g of a.i./ha.
合成了一系列新型三唑啉酮，并通过¹H NMR、元素分析和单晶X射线衍射分析对其结构进行了表征。针对稗草、升马唐、甘蓝型油菜和反枝苋评估了除草活性。除草活性数据表明，标题化合物中带有取代苄基部分的活性高于带有磺酰基、烷基等其他基团的化合物。为了进一步研究构效关系，基于除草活性数据进行了比较分子场分析。在这项工作中，比较分子场分析的空间和电场分布都吻合良好。结果表明，苯环邻位或对位周围的大体积吸电子基团可能会导致更高的活性。基于比较分子场分析，设计并合成了化合物I-23，其除草活性与市售除草剂乙羧氟草醚相当。在芽前300 g a.i./ha剂量下，对升马唐的活性为66.1%。
