Design, synthesis, and insecticidal bioactivities evaluation of pyrrole- and dihydropyrrole-fused neonicotinoid analogs containing chlorothiazole ring

Hong-Feng Shen Xi Chen Pin Liao Xu-Shen Shao Zhong Li Xiao-Yong Xu

Citation:  Hong-Feng Shen, Xi Chen, Pin Liao, Xu-Shen Shao, Zhong Li, Xiao-Yong Xu. Design, synthesis, and insecticidal bioactivities evaluation of pyrrole- and dihydropyrrole-fused neonicotinoid analogs containing chlorothiazole ring[J]. Chinese Chemical Letters, 2015, 26(5): 509-512. doi: 10.1016/j.cclet.2015.03.017 shu

Design, synthesis, and insecticidal bioactivities evaluation of pyrrole- and dihydropyrrole-fused neonicotinoid analogs containing chlorothiazole ring

    通讯作者: Xiao-Yong Xu,
  • 基金项目:

    This work was supported by National Key Technology R&D Program of China (No. 2011BAE06B01). (No. 2011BAE06B01)

摘要: Chlorothiazole ring, as a substituted heterocycle, frequently occurred in structures of various insecticides, and brought positive effect on bioactivity. In purpose to find novel neonicotinoids, a series of pyrrole- and dihydropyrrole-fused neonicotinoid analogs containing chlorothiazole ring were synthesized for the first time. Results of the following biological assays showed that compounds 5a-c achieved good insecticidal activity against Aphis craccivora, and compound 5h exhibited good activity against Nilaparvata lugens.

English

  • 
    1. [1] S. Kagabu, Discovery of imidacloprid and further developments from strategic molecular designs, J. Agric. Food Chem. 59 (2011) 2887-2896.[1] S. Kagabu, Discovery of imidacloprid and further developments from strategic molecular designs, J. Agric. Food Chem. 59 (2011) 2887-2896.

    2. [2] I. Ohno,M. Tomizawa, K.A. Durkin, et al., Bis-neonicotinoid insecticides: observed and predicted binding interactions with the nicotinic receptor, Bioorg. Med. Chem. Lett. 19 (2009) 3449-3452.[2] I. Ohno,M. Tomizawa, K.A. Durkin, et al., Bis-neonicotinoid insecticides: observed and predicted binding interactions with the nicotinic receptor, Bioorg. Med. Chem. Lett. 19 (2009) 3449-3452.

    3. [3] P. Jeschke, R. Nauen, Neonicotinoids-from zero to hero in insecticide chemistry, Pest Manag. Sci. 64 (2008) 1084-1098.[3] P. Jeschke, R. Nauen, Neonicotinoids-from zero to hero in insecticide chemistry, Pest Manag. Sci. 64 (2008) 1084-1098.

    4. [4] M. Tomizawa, J.E. Casida, Neonicotinoid insecticide toxicology: mechanisms of selective action, Annu. Rev. Pharmacool. Toxicol. 45 (2005) 247-268.[4] M. Tomizawa, J.E. Casida, Neonicotinoid insecticide toxicology: mechanisms of selective action, Annu. Rev. Pharmacool. Toxicol. 45 (2005) 247-268.

    5. [5] M. Matsumura, H. Takeuchi, M. Satoh, et al., Species-specific insecticide resistance to imidacloprid and fipronil in the rice planthoppers Nilaparvata lugens and Sogatella furcifera in East and South-east Asia, Pest Manag. Sci. 64 (2008) 1115-1121.[5] M. Matsumura, H. Takeuchi, M. Satoh, et al., Species-specific insecticide resistance to imidacloprid and fipronil in the rice planthoppers Nilaparvata lugens and Sogatella furcifera in East and South-east Asia, Pest Manag. Sci. 64 (2008) 1115-1121.

    6. [6] Z.Y. Wang, M.D. Yao, Y.D. Wu, Cross-resistance, inheritance and biochemical mechanisms of imidacloprid resistance in B-biotype Bemisia tabaci, Pest Manag. Sci. 65 (2009) 1189-1194.[6] Z.Y. Wang, M.D. Yao, Y.D. Wu, Cross-resistance, inheritance and biochemical mechanisms of imidacloprid resistance in B-biotype Bemisia tabaci, Pest Manag. Sci. 65 (2009) 1189-1194.

    7. [7] K. Gorman, G. Devine, J. Bennison, et al., Report of resistance to the neonicotinoid insecticide imidacloprid in Trialeurodes vaporariorum (Hemiptera: Aleyrodidae), Pest Manag. Sci. 63 (2007) 555-558.[7] K. Gorman, G. Devine, J. Bennison, et al., Report of resistance to the neonicotinoid insecticide imidacloprid in Trialeurodes vaporariorum (Hemiptera: Aleyrodidae), Pest Manag. Sci. 63 (2007) 555-558.

    8. [8] P. Jeschke, R. Nauen, M. Schindler, et al., Overview of the status and global strategy for neonicotinoids, J. Agric. Food Chem. 59 (2011) 2897-2908.[8] P. Jeschke, R. Nauen, M. Schindler, et al., Overview of the status and global strategy for neonicotinoids, J. Agric. Food Chem. 59 (2011) 2897-2908.

    9. [9] M. Bomgardner, Bee deaths and seed treatments, Chem. Eng. News 90 (2012) 12.[9] M. Bomgardner, Bee deaths and seed treatments, Chem. Eng. News 90 (2012) 12.

    10. [10] A. Kamel, Refined methodology for the determination of neonicotinoid pesticides and their metabolites in honey bees and bee products by liquid chromatography- tandem mass spectrometry (LC-MS/MS), J. Agric. Food Chem. 58 (2010) 5926-5931.[10] A. Kamel, Refined methodology for the determination of neonicotinoid pesticides and their metabolites in honey bees and bee products by liquid chromatography- tandem mass spectrometry (LC-MS/MS), J. Agric. Food Chem. 58 (2010) 5926-5931.

    11. [11] Z.J. Ye, L.N. Shi, X.S. Shao, et al., Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation, J. Agric. Food Chem. 61 (2013) 312-319.[11] Z.J. Ye, L.N. Shi, X.S. Shao, et al., Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation, J. Agric. Food Chem. 61 (2013) 312-319.

    12. [12] Z.Z. Tian, X.S. Shao, Z. Li, et al., Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification, J. Agric. Food Chem. 55 (2007) 2288-2292.[12] Z.Z. Tian, X.S. Shao, Z. Li, et al., Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification, J. Agric. Food Chem. 55 (2007) 2288-2292.

    13. [13] X.S. Shao, W.W. Zhang, Y.Q. Peng, et al., cis-Nitromethylene neonicotinoids as new nicotinic family: synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine, Bioorg. Med. Chem. Lett. 18 (2008) 6513-6516.[13] X.S. Shao, W.W. Zhang, Y.Q. Peng, et al., cis-Nitromethylene neonicotinoids as new nicotinic family: synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine, Bioorg. Med. Chem. Lett. 18 (2008) 6513-6516.

    14. [14] Y.F. Fan, W.W. Zhang, X.S. Shao, et al., Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives, Chin. Chem. Lett. 26 (2015) 1-5.[14] Y.F. Fan, W.W. Zhang, X.S. Shao, et al., Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives, Chin. Chem. Lett. 26 (2015) 1-5.

    15. [15] X.S. Shao, H. Fu, X.Y. Xu, et al., Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58 (2010) 2696-2702.[15] X.S. Shao, H. Fu, X.Y. Xu, et al., Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58 (2010) 2696-2702.

    16. [16] R.B. Xu, R. Xia, M. Luo, et al., Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues, J. Agric. Food Chem. 62 (2014) 381-390.[16] R.B. Xu, R. Xia, M. Luo, et al., Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues, J. Agric. Food Chem. 62 (2014) 381-390.

    17. [17] X.S. Shao, P.W. Lee, Z.W. Liu, et al., cis-Configuration: a new tactic/rationale for neonicotinoid molecular design, J. Agric. Food Chem. 59 (2011) 2943-2949.[17] X.S. Shao, P.W. Lee, Z.W. Liu, et al., cis-Configuration: a new tactic/rationale for neonicotinoid molecular design, J. Agric. Food Chem. 59 (2011) 2943-2949.

    18. [18] L. Novák, G. Hornyánszky, J. Rohály, et al., Preparation of novel hexythiazox analogues, Pest. Sci. 49 (1997) 85-89.[18] L. Novák, G. Hornyánszky, J. Rohály, et al., Preparation of novel hexythiazox analogues, Pest. Sci. 49 (1997) 85-89.

    19. [19] H. Takahiro, T. Tadaaki, K. Tooru, et al., Organophosphorus compounds as insecticides, miticides, and nematocides, Japan Patent 60104096, 1985.[19] H. Takahiro, T. Tadaaki, K. Tooru, et al., Organophosphorus compounds as insecticides, miticides, and nematocides, Japan Patent 60104096, 1985.

    20. [20] Y.M. Cui, Q.Q. Huang, J. Xu, et al., Identification of potent type I MetAP inhibitors by simple bioisosteric replacement. Part 1: Synthesis and preliminary SAR studies of thiazole-4-carboxylic acid thiazol-2-ylamide derivatives, Bioorg. Med. Chem. Lett. 15 (2005) 3732-3736.[20] Y.M. Cui, Q.Q. Huang, J. Xu, et al., Identification of potent type I MetAP inhibitors by simple bioisosteric replacement. Part 1: Synthesis and preliminary SAR studies of thiazole-4-carboxylic acid thiazol-2-ylamide derivatives, Bioorg. Med. Chem. Lett. 15 (2005) 3732-3736.

    21. [21] Q.M. Wang, H. Li, Y.H. Li, et al., Synthesis and herbicidal activity of 2-cyano-3- (2-chlorothiazol-5-yl)methylaminoacrylates, J. Agric. Food Chem. 52 (2004) 1918-1922.[21] Q.M. Wang, H. Li, Y.H. Li, et al., Synthesis and herbicidal activity of 2-cyano-3- (2-chlorothiazol-5-yl)methylaminoacrylates, J. Agric. Food Chem. 52 (2004) 1918-1922.

    22. [22] J.G. Samaritoni, D.A. Demeter, J.M. Gifford, et al., Dihydropiperazine neonicotinoid compounds. Synthesis and insecticidal activity, J. Agric. Food Chem. 51 (2003) 3035-3042.[22] J.G. Samaritoni, D.A. Demeter, J.M. Gifford, et al., Dihydropiperazine neonicotinoid compounds. Synthesis and insecticidal activity, J. Agric. Food Chem. 51 (2003) 3035-3042.

    23. [23] S. Suchail, D. Guez, L.P. Belzunces, Discrepancy between acute and chronic toxicity induced by imidacloprid and its metabolites in Apis mellifera, Environ. Toxicol. Chem. 20 (2001) 2482-2486.[23] S. Suchail, D. Guez, L.P. Belzunces, Discrepancy between acute and chronic toxicity induced by imidacloprid and its metabolites in Apis mellifera, Environ. Toxicol. Chem. 20 (2001) 2482-2486.

    24. [24] S.Y. Lu, X.S. Shao, Z. Li, et al., Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration, J. Agric. Food Chem. 60 (2012) 322-330.[24] S.Y. Lu, X.S. Shao, Z. Li, et al., Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration, J. Agric. Food Chem. 60 (2012) 322-330.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  927
  • HTML全文浏览量:  22
文章相关
  • 发布日期:  2015-03-28
  • 收稿日期:  2014-12-23
  • 网络出版日期:  2015-01-28
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章