有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1772-1779. 上一篇    下一篇

研究简报

新型含硫(氧)肟醚衍生物的合成、杀虫活性及其结构活性关系研究

柳爱平*,a,b 王晓光a 欧晓明a 刘曙东a
莫洪波a,c 刘兴平a 王婷瑾a,b 何海军a,c
胡 礼a 黄明智a 刘钊杰b 姚建仁b,d
  

  1. (a湖南化工研究院国家农药创制工程技术研究中心 长沙 410007)
    (b华中师范大学有机合成研究所 武汉 430079)
    (c湖南师范大学化学化工学院 长沙 410081)
    (d中国农科院植物保护研究所 北京 100094)
  • 收稿日期:2007-03-11 修回日期:2008-04-01 出版日期:2008-10-20 发布日期:2008-10-20
  • 通讯作者: 柳爱平

Synthesis and Insecticidal Activities of Novel Sulfur(oxygen) Con-taining Oxime Ethers as well as Structure Activity Relationship

LIU, Ai-Ping*,a,b WANG, Xiao-Guanga OU, Xiao-Minga LIU, Shu-Donga
MO, Hong-Boa,c LIU, Xin-Pinga WANG, Ting-Jina,b HE, Hai-Juna,c
HU, Lia HUANG, Ming-Zhia LIU, Zhao-Jieb YAO, Jian-Renb,d

  

  1. (a National Engineering Research Center for Agrochemicals, Hunan Research Institute of
    Chemical Industry, Changsha 410007)
    (b Institute of Organic Synthesis, Central China Normal University, Wuhan 430079)
    (c College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081)
    (d Institute of Plant Protection, China Academy of Agricultural Sciences, Beijing 100094)
  • Received:2007-03-11 Revised:2008-04-01 Online:2008-10-20 Published:2008-10-20
  • Contact: LIU, Ai-Ping

通过1-芳基含硫(氧)酮肟与相应的拟除虫菊醇卤化物在氢氧化钠和相转移催化剂条件下反应或1-芳基含硫(氧)酮肟与相应的拟除虫菊醇卤化物的三乙基季胺盐在氢氧化钠条件下反应, 合成了1-芳基含硫(氧)酮O-苄基肟醚C1~C96共96个化合物. 它们的结构经质谱, 1H NMR, IR和元素分析确证. 生物活性测定结果表明, 该类化合物对鳞翅目和同翅目害虫表现出显著活性, C74和C93对粘虫、叶蝉的活性[LC50/(mg•L-1)]分别为1.4, 0.63和0.31, 1.2. 优于对照药氰戊菊酯.

关键词: 含硫(氧)肟醚, 杀虫活性, 鳞翅目害虫, 同翅目害虫

96 novel sulfur(oxygen) containing 1-aryl O-benzyl oximes were synthesized by the reaction of sulfur(oxygen) containing 1-aryl oximes with the corresponding halides of pyrethriod alcohols in the pres-ence of sodium hydroxide and phase transfer catalyst or with triethylquaternary ammonium salts of halides of pyrethriod alcohol in the presence of sodium hydroxide. The title compounds were identified by MS, 1H NMR, IR spectra and elemental analyses. Bioassay showed that these compounds showed remarkable insec-ticidal activities against homopteran and lepidopteran pests. C74 and C93 showed a medial effective dose [LC50/(mg• L-1)] of 1.4, 0.63 and 0.31, 1.2 against oriental army worm and leafhopper respectively, the LC50 values of compounds C74 and C93 were better than that of the commercialized insecticide fenvalerate.

Key words: insecticidal activity, sulfur(oxygen) containing oxime ether, homoptera, lepidoptera