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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (9): 1130-1136. Previous Articles     Next Articles

Original Articles

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

庞怀林a,b，阳海a，尹笃林*,a，雷满香b
黄明智b，毛春晖b，李文安a   

  1. (a湖南师范大学化学化工学院 长沙 410081)
    (b湖南化工研究院 长沙 410007)
  • 收稿日期:2006-11-23 修回日期:2004-04-06 发布日期:2007-08-30
  • 通讯作者: 尹笃林

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

PANG Huai-Lina,b,YANG Haia, YIN Du-Lin*,a,LEI Man-Xiangb
HUANG Ming-Zhib,MAO Chun-Huib,LI Wen-Ana   

  1. (a College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081)
    (b Hunan Research Institute of Chemical Industry, Changsha 410007)
  • Received:2006-11-23 Revised:2004-04-06 Published:2007-08-30
  • Contact: YIN Du-Lin

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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.

Key words: synthesis, herbicidal activity, 2-oxopyrrolidine, insecticidal activity, 3,4-dihydro-2H-1,4-benzoxazin-3-one