N-取代-6-(3-氯-4-氯甲基-2-氧吡咯烷-1-基)-7-氟-3,4-二氢-2H-1,4-苯并噁嗪-3-酮衍生物的合成与生物活性研究

采用生物活性基团拼接的分子设计方法, 将活性基团2-氧吡咯烷引入到2H-1,4]苯并噁嗪-3(4H)-酮分子结构的苯环上, 设计并合成了16个未见文献报道的N-取代-6-(3-氯-4-氯甲基-2-氧吡咯烷-1-基)-7-氟-3,4-二氢-2H-1,4-苯并噁嗪-3-酮衍生物6a～6p, 其结构经IR, ¹H NMR, LC/MS和元素分析确证. 初步的生物活性测试结果表明, 部分化合物具有较高的除草和杀虫活性, 如6c～6f等化合物在用量为150 g/hm²时对苘麻(Abutilon theophrasti)、刺苋(Amaranthus spinosus)和藜(Chenopodium album L)等阔叶杂草具有90%以上的抑制率, 6l和6o在500 mg/L浓度下对蚕豆蚜(Aphis fabae)具有90%以上的致死率, 个别化合物还兼具除草及杀虫活性.

Synthesis and Biological Activity of N-Alkyl-6-(3-chloro-4-chloromethyl-2-oxopyrrolidin-1-yl)-7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one Derivatives

In order to find novel pesticides with high activities, low toxicities and low residues, sixteen novel N-alkyl-6-(3-chloro-4-chloromethyl-2-oxopyrrolidin-1-yl)-7-fluoro-3,4-dihydro-2H-1,4-benzoxazin- 3-one derivatives 6a～6p were designed and synthesized. Their structures were confirmed by IR, ¹H NMR, LC/MS spectra and elemental analysis. The results of preliminary bioassay indicated that some title compounds exhibited obvious biological activities, for example, com-pounds 6c～6f showed more than 90% herbicidal activities against Abutilon theo-phrasti, Amaranthus spinosus and Chenopodium album L. at 150 g/hm², and compounds 6l and 6o exhibited more than 90% insecticidal activities against Aphis fabae at 500 mg/L. It was also revealed that compounds 6d and 6e exhibited not only good herbicidal activities but also excellent insecticidal activities.