含二茂铁基新型植物生长调节剂的合成与生物活性研究

发布时间：2018-05-11 21:15

  本文选题：二茂铁 + 植物生长调节剂　； 参考：《西北大学》2011年硕士论文

【摘要】：植物生长调节剂作为农药的一个重要组成部分,在调节植物生长、增加粮食产量方面发挥着巨大的作用。随着人口、耕地与环境日益增加的矛盾,传统的农药暴露出越来越多的缺点,形势要求必须不断地研发对环境友好的超高效、安全、新颖的绿色农药以迎接挑战。 酰基硫脲类化合物以其杀菌、杀虫、除草和调节植物生长调节等活性引起了农药界的关注,被誉为“21世纪的农药”,一度成为农药研究的热点。本文通过文献检索,对植物生长调节剂的发展、应用、酰基硫脲类化合物的生物活性与合成方法以及二茂铁类化合物的生物活性做了比较全面的综述。根据生物等排原理及亚结构连接法,我们以酰基硫脲类化合物为先导化合物,进行分子设计、优化结构,引入具有生物活性的二茂铁基团,利用异硫氰酸酯和芳胺在无水非质子性溶剂中反应得到目标产物。设计合成出两个系列共18种新的酰基硫脲类化合物。它们的结构经IR、1HNMR以及元素分析确认。另外,我们对目标化合物的合成条件、理化性质、波谱特点进行了系统的分析和探讨,同时对化合物Ⅱ3进行了X-射线单晶衍射,进一步表明酰基硫脲类化合物中形成了六元环的分子内氢键。 设计合成的化合物结构如下： 系列ⅠN-二茂铁甲酰基-N'-芳基双(单)硫脲类衍生物 系列ⅡN-芳甲酰基(芳氧乙酰基)-N'-二茂铁基硫脲类衍生物Ⅱ1-Ⅱ6 -C6H5 2-FC6H4- 4-FC6H4- 2-ClC6H4- 4-CH3C6H4- 2-OCH3C6H4-Ar=Ⅱ7-Ⅱ9 C6H5OCH2- 4-CH3C6H40CH2- 4-OCH3C6H40CH2- 考虑到二茂铁衍生物的低毒性,我们设想将酰基硫脲类衍生物中的芳香环全部用二茂铁代替,进而增加化合物中铁含量,以期具有良好的活性。设计分子结构如下： 本论文中将其编号为Ⅱ10。 此外,采用萝卜子叶扩张法和小麦芽鞘切断试法对所合成的硫脲类化合物进行初步的植物生长调节活性测试,结果表明,所有化合物均表现出一定的生物活性。其中化合物Ⅰ5、Ⅰ6、Ⅰ7、Ⅰ8、Ⅱ2、Ⅱ8均表现出较高的生长素活性,部分化合物的活性略高于吲哚乙酸。化合物Ⅱ7、Ⅱ10的细胞分裂素活性接近激动素。我们所合成的不含苯环的酰基硫脲类化合物Ⅱ10在高浓度时表现出较强的细胞分裂素活性,同时也具备一定生长素活性。
[Abstract]:As an important component of pesticides, plant growth regulators play an important role in regulating plant growth and increasing grain yield. With the increasing contradiction between population, cultivated land and environment, the traditional pesticides are exposed to more and more shortcomings. The situation requires the development of environmentally friendly super efficient, safe and novel green pesticides to meet the challenge. Acyl thiourea compounds have attracted the attention of the pesticide field because of their activities of sterilization, insecticidal, herbicidal and plant growth regulation, and have been praised as "pesticides in the 21st century", and have been the focus of pesticide research for a long time. In this paper, the development and application of plant growth regulators, the biological activities and synthesis methods of acyl thiourea compounds and the biological activities of ferrocene compounds are reviewed. On the basis of the principle of biological iso-arrangement and the method of substructure joining, we used acyl thioureas as lead compounds to design molecules, optimize the structure, and introduce ferrocene groups with biological activity. The target product was obtained by the reaction of isothiocyanates and aromatic amines in anhydrous anprotonic solvents. Two series of 18 new acyl thiourea compounds were designed and synthesized. Their structures were confirmed by IR 1H NMR and elemental analysis. In addition, the synthetic conditions, physicochemical properties and spectral characteristics of the target compound were systematically analyzed and discussed. Meanwhile, the X-ray single crystal diffraction of compound 鈪，

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