N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-取代基硫脲衍生物的合成及杀虫活性的研究

doi:10.3969/j.issn.0253-2417.2015.02.002

摘要/Abstract

摘要： 为了寻求无公害的杀虫剂,设计合成了系列新型的含有去氢枞酸骨架的1,3,4-噻二唑衍生物。利用 ¹H NMR、IR、MS和元素分析等手段对所合成新化合物进行了分析和表征。探讨了化合物对棉铃虫(Helicoverpa armigera)、玉米螟(Ostrinia nubilalis)和小菜蛾(Plutella xylostella)的杀虫活性。研究表明在200 mg/L质量浓度下,化合物N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-苯基硫脲(3a)和N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-间甲基苯基硫脲(3c)对棉铃虫具有良好的杀虫活性,防效率分别达到93.3%和83.3%,而化合物N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-邻甲基苯基硫脲(3b)、N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-间甲基苯基硫脲(3c)、N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-对甲基苯基硫脲(3d)和N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-对氯苯基硫脲(3i)对玉米螟具有一定的杀虫活性,防效率分别为66.7%、66.7%、73.3%和60%;此外,对化合物构效关系也进行了讨论,发现苯环上4位取代基对棉铃虫和玉米螟的防效率贡献分别为H>CH₃ > Cl > CF₃ > OCH₃ > Br=F和CH₃ > Cl > Br > F > H=CF₃ > OCH₃。

关键词: 去氢枞酸, 1,3,4-噻二唑, 硫脲, 合成, 杀虫活性

Abstract: In order to search for biorational pesticides, a series of novel 1,3,4-thiadiazole thiourea derivatives (3a-3k) containing dehydroabietic acid (DHA) structure were designed and synthesized. Their structures were characterized by IR, MS, NMR, and elemental analysis. The insecticidal activities were investigated against cotton bollworm (Helicoverpa armigera), corn borer (Ostrinia nubilalis), and diamondback moth (Plutella xylostella). The preliminary bioassay showed that, at the concentration of 200 mg/L, compounds 3a and 3c exhibited excellent insecticidal activities against H. armigera, with mortality rates of 93.3% and 83.3%, respectively, and compounds 3b, 3c, 3d, and 3i displayed moderate insecticidal activities against O. nubilalis with mortality rates of 66.7%, 66.7%, 73.3%, and 60%, respectively. In addition, the structure-insecticidal activity relationship of these compounds was discussed,too.

Key words: dehydroabietic acid, 1,3,4-thiadiazole, thiourea, synthesis, insecticidal activity

中图分类号:

TQ35

莫启进, 刘陆智, 段文贵, 岑波, 林桂汕, 陈乃源, 黄艳, 刘布鸣. N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-取代基硫脲衍生物的合成及杀虫活性的研究[J]. 林产化学与工业, 2015, 35(2): 8-16.

MO Qi-jin MO Qi-jin, LIU Lu-zhi, DUAN Wen-gui, CEN Bo, LIN Gui-shan, CHEN Nai-yuan, HUANG Yan, LIU Bu-ming. Synthesis and Insecticidal Activities of N-(5- Dehydroabietyl-1,3,4-thiadiazol-2-yl)- N'-substituted Thioureas[J]. Chemistry and Industry of Forest Products, 2015, 35(2): 8-16.

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