【作者】 张剑；

【导师】 马希汉； 周文明；

【作者基本信息】 西北农林科技大学 ， 应用化学， 2011， 硕士

【摘要】 近年来,杂环化合物在抑菌、除草以及杀虫等植物保护领域以其高效、低毒和对环境友好的特点,在新农药的开发研制领域受到极大的关注。喹啉类化合物是氮杂环中非常重要的一类化合物,在医疗保健和植物保护领域具有广泛的应用性和良好的发展前景,是抗肿瘤、抗艾滋病毒等药物的重要前体化合物,同时在新型绿色农药的创制中也占据着重要地位。基于此,本论文设计以邻氨基苯甲酸,对氯邻氨基苯甲酸和5-甲基邻氨基苯甲酸为原料,通过酯化、酰化、环合再酯化的合成路线合成了24个喹啉-2,4-二酮类衍生物,化合物结构均经1~H-NMR、IR和ESI-MS等波谱手段予以确认,所有化合物均未见文献报道。对新化合物进行三龄粘虫的拒食活性和毒杀活性研究,希望能为高效低毒的新型杀虫剂的创制奠定一定的理论基础。初步杀虫活性测试结果表明,在100 mg/L浓度下,24种化合物对三龄粘虫均有不同程度的拒食活性和毒杀活性。实验数据表明,喹啉环上3位取代基为2,4-二氯苯时活性要优于3位取代基为3,4-二氯苯基的化合物,例如,化合物M3b对粘虫的校正死亡率达到19.28%,而化合物M4b的校正死亡率只有10.00%;喹啉环中苯环上的取代基的类型与位置的不同对化合物杀虫活性差异并无明显影响,例如M1a、M2d和M3e三种化合物对粘虫的校正死亡率分别为17.20%、16.92%和14.96%,差别不大;对4位羟基酯化衍生后,发现使用可α-甲基丙烯酰氯进行酯化的化合物的活性要优于同中间体衍生的其他化合物,例如,化合物M1a对粘虫的校正死亡率在48 h时达到17.20%,接近吡虫啉22.86%的校对死亡率,也明显高于同一中间体衍生的其他化合物M1b(8.00%)、M1c(4.00%)、M1d(8.00%)和M1e(8.62%)。更多还原

【Abstract】 In recent years, heterocyclic compounds are used to research and develop new pesticides because of theirs features of high efficiency, low toxicity and environmentally friendly in the areas of antibacterial, herbicidal and insecticidal plant protection.Quinoline compounds are a very important class of heterocyclic compounds, which have wide application and good prospects for development in the field of health care and plant protection. They are important precursor compounds of the drug for the anti-tumor, anti-HIV drugs and so on, while are also occupy an important position on created of new green pesticidesBased on this, the paper designed to use anthranilic acid, p-chloro anthranilic acid and 4- methyl anthranilic acid as raw materials ,we synthesized 24 quinoline-2,4-dione derivatives by esterification , acylation, cyclization and then esterification,and all the synthesized compounds were characterized by IR, NMR and ESI-MS,and the derivatives were first studied.All the compounds were studied for antifeedant activity and insecticidal activity of third M. separata, in order to find new efficiency and low toxicity pesticidesThe insecticidal activity results showed as fowllows: the 24 compounds has differerntly ntifeedant activity and insecticidal activity for third M. separata at concentration of 100 mg/L. Experimental data show, the activity for the compounds of the third position of the quinoline ring are substituted by 2,4 - dichlorobenzene of is better than the compounds which substituted by the 3,4 - dichloro-phenyl, such as the mortality rate of M3b is 19.28%, higher than M4b(10.00%). The compounds that have different types and locations’substituents on the benzene ring of the quinoline ring have no significant difference in effects of insecticidal activity, for example the mortality rates of M1a, M2d and M3e are 17.20%, 16.92% and 14.96%, the difference is small; the derivatives that 4-hydroxy were esterified by a- Methacryloyl chloride , have higher insecticidal activity than other derivatives which were derived from the same intermediates but esterified by other differet acyl chloride , for example M1a which mortality rate reached 17.20% in 48 h, close to Imidacloprid (22.86%) ,and higher than the other compounds derived from the same intermediate M1b (8.00 %), M1c (4.00%), M1d (8.00%) and M1e (8.62%).更多还原