杀菌剂啶酰菌胺合成新工艺
A New Process for the Synthesis of Fungicide Pyridylamide
摘要: 啶酰菌胺是一种新型广谱性的烟酰胺类杀菌剂。目前,国内外文献中,合成啶酰菌胺的相关路线的报道较多,本文简单的总结了其合成路线,并对中间体4-氯-2’-氨基联苯的合成方法也作了一定的阐述。在现有的合成方法的基础上,提出以邻溴硝基苯为起始原料,经过还原,与对氯苯硼酸通过Suziki偶联反应,合成4-氯-2’-氨基联苯,再与2-氯烟酰氯缩合,得到目标产物。总收率达到92%,纯度达到95%以上。此合成路线原料易得,步骤简单,收率高,降低了生产成本,适合工业化生产。
Abstract: Boscalid is a new broad-spectrum nicotinamide fungicide. At present, there are many reports about the synthesis of boscalid in the literature at home and abroad. In this paper, the synthesis process of boscalid is simply summarized, and the synthesis method of intermediate 4-chloro-2’-aminobiphenyl is also described. On the basis of the existing synthesis method, it is proposed to synthesize 4-chloro-2’-aminobiphenyls from o-bromonitrobenzene through reduction and Suziki coupling reaction with p-chlorobenzoboric acid, and then condense with 2-chloronicotinyl chloride to obtain the target product. The total yield is 92% and the purity is over 95%. The raw material of this synthetic route is easy to obtain, the steps are simple, the yield is high, the production cost is reduced, and it is suitable for industrial production.
文章引用:顾旻旻, 尹凯, 柴华强, 于江, 吴浩. 杀菌剂啶酰菌胺合成新工艺[J]. 化学工程与技术, 2020, 10(4): 237-241. https://doi.org/10.12677/HJCET.2020.104030

参考文献

[1] Buberl, J., Broscious, S., Ypema, H., et al. (2005) Method of Plant Growth Promotion Using Amide Compounds: WO 2005018324. 2005-03-03.
[2] 颜范勇. 新型烟酰胺类杀菌剂–啶酰菌胺[J]. 农药, 2008, 47(2): 132-135.
[3] 杨吉春, 张金波, 刘长令. 酰胺类杀菌剂新品种开发进展[J]. 农药, 2008, 47(1): 6-9.
[4] Zierke, T. and Maywald, V. (2012) Preparation of 2-Aminobiphenylenes. WO 2010094736. 2012-01-18.
[5] Jasch, H. Scheumann, J. and Heinrich, M.R. (2012) Regioselective Radical Arylation of Anilines with Arylhydrazines. The Journal of Organic Chemistry, 77, 10699-10706. [Google Scholar] [CrossRef] [PubMed]
[6] Glasnov, T.N. and Kappe, C.O. (2010) Toward a Con-tinuous-Flow Synthesis of Boscalid. Advanced Synthesis & Catalysis, 352, 3089-3097.
[Google Scholar] [CrossRef
[7] Strunz, G.M. and Finlay, H. (1994) Concise, Efficient New Synthesis of Pipercide, an Insecticidal Unsaturated Amide from Piper nigrum, and Related Compounds. Tetrahedron, 38, 11113-11122. [Google Scholar] [CrossRef
[8] 迟会伟. 啶酰菌胺的合成与生物活性研究[J]. 农化新世纪, 2008, 9(1): 39-40.
[9] Karl, E., Joachim, G., et al. (2000) Process for Preparing Nitrobiphenylene. US 6087542. 2000-1-11.
[10] 易苗, 尹新. 一种铈改性负载性镍基催化剂及其制备方法和应用[P]. CN 106902835B. 2019-07-09.