2-酰基-氰基乙酸衍生物的合成及生物活性

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (9): 1798.

2-酰基-氰基乙酸衍生物的合成及生物活性

李洋^1,2, 张志国^2,3, 迟会伟², 罗艳梅², 刘长令², 李正名¹

1. 南开大学元素有机化学国家重点实验室, 元素有机化学研究所, 天津 300071;
2. 沈阳化工研究院, 沈阳 110021;
3. 沈阳化工学院化学系, 沈阳 110142

收稿日期:2009-12-01 出版日期:2010-09-10 发布日期:2010-09-10
通讯作者: 李正名, 男, 教授, 博士生导师, 中国工程院院士, 主要从事有机化学和农药化学研究. E-mail: nkzml@vip.163.com
基金资助:
国家“十一五”科技支撑项目(批准号: 2006BAE01A01-2)资助.

Synthesis and Bioactivity of 2-Aceto-cyanoacetic Acid Derivatives

LI Yang^1,2, ZHANG Zhi-Guo^2,3, CHI Hui-Wei², LUO Yan-Mei², LIU Chang-Ling², LI Zheng-Ming^1*

1. State Key Laboratory of Elemento-Organic Chemistry, National Pesticides Engineering Resarch Center, Nankai University, Tianjin 300071, China;
2. Shenyang Research Institute of Chemical Industry, Shenyang 110021, China;
3. College of Applied Chemistry, Shenyang Institute of Chemical Technology, Shenyang 110142, China

Received:2009-12-01 Online:2010-09-10 Published:2010-09-10
Contact: LI Zheng-Ming. E-mail: nkzml@vip.163.com
Supported by:
国家“十一五”科技支撑项目(批准号: 2006BAE01A01-2)资助.

摘要/Abstract

摘要： 设计并合成了21个新型2-酰基-氰基乙酸类化合物, 应用氢核磁共振谱、元素分析和红外光谱验证了它们的结构, 并测试了其生物活性. 部分化合物对朱砂叶螨(Tetranychus cinnabarinus)具有活性, 化合物4e和4k在600 mg/L浓度下呈现100%的杀螨活性; 部分化合物具有一定杀菌和除草活性, 化合物4k和4s在400 mg/L浓度下对小麦白粉病(Blumeria graminis)的抑制率达到100%, 化合物4m在1000 mg/L浓度下可以很好地防治苘麻(Abutilon theophrasti). 初步探讨了化合物结构与生物活性关系.

关键词: 2-酰基氰基乙酸衍生物, 杀螨活性, 杀菌活性, 除草活性

Abstract: For finding excellent acaricide, a series of novel 2-acyl-cyanoacetic acid derivatives was designed and synthesized based on cyflumetofen. Their structures were confirmed by ¹H NMR, IR and elemental analysis. Preliminary biological evaluation showed that several compounds had acaricidal activity, with compounds 4e and 4k having 100% control against Tetranychus cinnabarinus at 600 mg/L. Some compounds exhibited fungicidal activity and herbicidal activity, compounds 4k and 4s could completely control against Blumeria graminis at 400 mg/L, compound 4m had good control of Abutilon theophrasti at 1000 mg/L. The relationship between the structures and the biological activity was also discussed.

Key words: 2-Acyl-cyanoacetic acid derivative, Acaricidal activity, Fungicidal activity, Herbicidal activity

TrendMD:

李洋, 张志国, 迟会伟, 罗艳梅, 刘长令, 李正名. 2-酰基-氰基乙酸衍生物的合成及生物活性. 高等学校化学学报, 2010, 31(9): 1798.

LI Yang, ZHANG Zhi-Guo, CHI Hui-Wei, LUO Yan-Mei, LIU Chang-Ling, .... Synthesis and Bioactivity of 2-Aceto-cyanoacetic Acid Derivatives. Chem. J. Chinese Universities, 2010, 31(9): 1798.

参考文献

[1]Richard S. A., Field T. J.. Proc. Chem. Soc.[J], 1908, 23: 249 [2]Franz P.. Arch. Pharm.[J], 1929, 267: 325—352 [3]Paul R., Caspar E., Hegedus B.. Helvetica. Chimica. Acta[J], 1937, 20: 250—263 [4]Satyendra K., Labhu R., Nath R. J.. Univ. Lahore. India. J. Indian Chem. Soc.[J], 1946, 23: 365—370 [5]Alain V., Jacques D.. Fac. Sci. Lyon, Fr. Compt. Rend.[J], 1961, 252: 3598—3600 [6]Masahiko I., Seiji N., Tadashi K.. Cyanoketone Derivative and Herbicide Containing It as an Acitive Component, EP 506373[P], 1992 [7]Masahiko I., Tadashi K.. Erbicides Containing Quinolinic Acid and Cyanoketone Derivatives, JP 06145007[P], 1994 [8]Masahiko I., Seiji O.. Preparation of [(Cyanoalkoxy)phenoxy]heterocycle Derivatives and Analogs as Herbicides, JP 05339224[P], 1992 [9]Nobuyoshi T., Satoshi G., Naoki I., Yasuhiro S.. Preparation of Benzoylcyanoacetic Acid Esters as Miticides, WO 2002014263[P], 2000 [10]Yasushi S., Renpei H., Masao Y., Satoru M.. Preparation of Oximes and Their Use as Insecticides and Acaricides, JP 2002241358[P], 2001 [11]Hiroshi M., Yoshiyuki K., Shinji T.. Acylacetonitriles and Agrochemical Pesticides Containing Them, JP 2003286265[P], 2002 [12]Zhang X. M., Yang D. L., Liu Y. C.. J. Org. Chem.[J], 1989, 11(3): 281—300 [13]LI Yang(李洋), ZHANG Hong(张弘), LIU Yuan-Xiong(刘远雄), ZHOU Yin-Ping(周银平), LUO Yan-Mei(罗艳梅), LIU Chang-Ling(刘长令). Chinese J. Pesticides(农药)[J], 2009, 48(7): 474—475, 478 [14]Liu C. L., Li L., Li Z. M.. Bioorg. Med. Chem.[J], 2004, 14(12): 2825—2830 [15]LI Miao(李淼), ZHANG Jin-Bo(张金波), YANG Ji-Chun(杨吉春), LI Zhi-Nian(李志念), LIU Chang-Ling(刘长令), LI Zheng-Ming(李正名). Chem. J. Chinese Universities(高等学校化学学报)[J], 2009, 30(7): 1348—1352