有机化学 ›› 2017, Vol. 37 ›› Issue (9): 2343-2351.DOI: 10.6023/cjoc201703022 上一篇    下一篇

研究论文

新型含三氟丁烯的1,3,4-噁二唑(噻二唑)硫醚类衍生物的合成及杀线虫活性研究

陈学文, 甘秀海, 陈吉祥, 陈永中, 王艳娇, 胡德禹, 宋宝安   

  1. 贵州大学精细化工研究开发中心 绿色农药与农业生物工程国家重点实验室培育基地教育部重点实验室 贵阳 550025
  • 收稿日期:2017-03-13 修回日期:2017-04-15 出版日期:2017-09-25 发布日期:2017-05-10
  • 通讯作者: 宋宝安 E-mail:songbaoan22@yahoo.com
  • 基金资助:

    国家自然科学基金(No.21672044)、国家地方性高校合作计划(No.20147001)资助项目.

Synthesis and Nematicidal Activity of Novel 1,3,4-Oxadiazole (Thiadiazole) Thioether Derivatives Containing Trifluorobuten Moiety

Chen Xuewen, Gan Xiuhai, Chen Jixiang, Chen Yongzhong, Wang Yanjiao, Hu Deyu, Song Baoan   

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2017-03-13 Revised:2017-04-15 Online:2017-09-25 Published:2017-05-10
  • Contact: 10.6023/cjoc201703022 E-mail:songbaoan22@yahoo.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21672044) and the Provincial University Cooperation Plan of China (No. 20147001).

为了寻求结构新颖的高活性杀线虫化合物,通过活性亚结构组合方法,设计并合成了一系列含三氟丁烯的1,3,4-噁二唑(噻二唑)硫醚类衍生物,通过IR,1H NMR,13C NMR,ESI-MS和元素分析对其结构进行了表征.杀线虫活性测试结果显示,化合物5a6b在施药48 h后对秀丽线虫具有明显的毒杀活性,LC50分别为21.92和44.94 μg/mL,明显优于对照药剂噻唑膦(72.52 μg/mL)和氟噻虫砜(72.96 μg/mL).另外,在浓度为100 μg/mL下,大多数化合物对柑橘线虫表现出较好的毒杀活性,其中化合物5b在给药48和72 h后,对柑橘线虫的毒杀活性分别为79.9%和96.7%,优于对照药剂噻唑膦和氟噻虫砜.

关键词: 1,3,4-噁二唑(噻二唑)硫醚, 三氟丁烯, 杀线虫活性, 秀丽隐杆线虫, 柑橘线虫

In order to explore novel leading compound with good nematicidal activity, a series of 1,3,4-oxadiazole (thiadiazole) thioether derivatives containing a trifluorobuten group were designed and synthesized, and their structures were identified by IR, 1H NMR, 13C NMR spectra, ESI-MS and elemental Anal. ysis. The results of nematicidal activity assays revealed that compounds 5a and 6b possessed excellent nematicidal activity agaist Caenorhabditis elegans in vitro after 48 h, with LC50 values of 21.92 and 44.94 μg/mL, respectively, which were superior than that of fosthiazate (72.52 μg/mL) and fluensulfone (72.96 μg/mL). Furthermore, most of compounds exhibited moderate activity against Tylenchus semipenetranss at 100 μg/mL, compound 5b showed better nematicidal activity than fosthiazate and fluensulfone after 48 h and 72 h with the values of 79.9% and 96.7%.

Key words: 1,3,4-oxadiazole (thiadiazole) thioether, trifluorobutene, nematicidal activity, Caenorhabditis elegans, Tylenchus semipenetranss