Synthesis and Antifungal Activity of Substituted 2-Aryl Benzimidazoles Derivatives
Daye Huang
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorFang Qiu
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorZhigang Zhang
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorLiqiao Shi
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorChunxia Cao
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorCorresponding Author
Shaoyong Ke
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
E-mail: [email protected]Search for more papers by this authorDaye Huang
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorFang Qiu
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorZhigang Zhang
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorLiqiao Shi
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorChunxia Cao
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
Search for more papers by this authorCorresponding Author
Shaoyong Ke
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan, 430064 China
E-mail: [email protected]Search for more papers by this authorAbstract
Benzimidazole fungicides were among the early systemic fungicides developed and used for controlling a wide variety of plant diseases. During the course of our screening process for active compounds, two 2-aryl benzimidazoles derivatives bearing sulfoxide group (6b and 6c) have been demonstrated to exhibit good inhibition activity against high-resistant isolate of Botrytis cinerea compared with carbendazim, and the inhibition rates are up to 46.67% and 51.11% at the concentration of 10 μg/mL, which might be considered as the active framework for the discovery of novel fungicide to high-resistant isolate of B. cinerea.
Supporting Information
| Filename | Description |
|---|---|
| jhet3639-supp-0001-Figure_S1.docWord document, 163.5 KB |
Figure S1. 1H NMR spectra of compound 5c Figure S2. 1H NMR spectra of compound 6c |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References and Notes
- 1Delp, C. J. Benzimidazoles and related compounds; In Modern Selective Fungicides; H. Lyr Ed.; Gustav Fischer: New York, 1995, p. 291.
- 2Sevastos, A.; Labrou, N. E.; Flouri, F.; Malandrakis, A. Pestic. Biochem. Phys. 2017, 141, 23.
- 3Steffens, J. J.; Pell, E. J.; Tien, M. Curr. Opin. Biotechnol. 1996, 7, 348.
- 4Ma, Z.; Michailides, T. J. Crop Prot 2005, 24, 853.
- 5Davidse, L. C. Annu. Rev. Phytopathol. 1986, 24, 435.
- 6Koenraadt, H.; Somerville, S. C.; Jones, A. L. Phytopathology 1992, 82, 1348.
- 7Williamson, B.; Tudzynski, B.; Tudzynski, P.; Kan, A. L. V. Mol. Plant Pathol. 2007, 8, 561.
- 8Beever, R. E.; Laracy, E. P.; Pak, H. A. Plant Pathol. 2007, 38, 427.
- 9Banno, S.; Fukumori, F.; Ichiishi, A.; Okada, K.; Uekusa, H.; Kimura, M.; Fujimura, M. Phytopathology , 98, 397.
- 10Ziogas, B. N.; Nikou, D.; Markoglou, A. N.; Malandrakis, A. A.; Vontas, J. Eur. J. Plant Pathol. 2009, 125, 97.
- 11Sun, H. Y.; Wang, H. C.; Chen, Y.; Li, H. X.; Chen, C. J.; Zhou, M. G. Plant Dis. 2010, 94, 551.
- 12Katan, T.; Elad, Y.; Yunis, H. Plant Pathol 2010, 38, 86.
- 13Leroch, M.; Kretschmer, M.; Hahn, M. J. Phytopathol 2010, 159, 63.
- 14Zhang, C. Q.; Liu, Y. H.; Zhu, G. N. Eur. J. Plant Pathol. 2010, 126, 509.
- 15Malandrakis, A.; Markoglou, A.; Ziogas, B. Pestic Biochem Phys 2011, 99, 118.
- 16Fan, F.; Li, N.; Li, G. Q.; Luo, C. X. Plant Dis 2016, 100, 2414.
- 17Liu, S.; Che, Z. P.; Chen, G. Q. Crop Prot 2016, 84, 56.
- 18Lu, X. H.; Jiao, X. L.; Hao, J. J.; Chen, A. J.; Gao, W. W. Eur. J. Plant Pathol. 2016, 144, 467.
- 19Aly, A. A.; Brown, A. B.; Hassan, A. A.; Gomaa, M. A.-M.; Nemr, F. M. J. Sulfur Chem. 2015, 36, 502.
- 20Ke, S. J Heterocyclic Chem 2017, 54, 1957.
- 21Zhao, J.; Jiang, X. Chin Chem Lett. 2018, 29, 1079.
- 22Saeed, A.; Flörke, U.; Erben, M. F. J Sulfur Chem 2014, 35, 318.
- 23Wu, J.; Shen, C.; Zhang, H.; Lu, W.; Zhang, Y.; Wang, C. J Environ Manage 2015, 161, 11.
- 24Oka, Y. Pest Manag Sci 2014, 70, 1850.
- 25Mori, T.; Wang, J.; Tanaka, Y.; Nagai, K.; Kawagishi, H.; Hirai, H. J. Hazard. Mater. 2017, 321, 586.
- 26Jeschke, P.; Nauen, R.; Schindler, M.; Elbert, A. J. Agric. Food Chem. 2011, 59, 2897.
- 27Chen, X.; Wang, D.; Huang, J.; Huang, Y.; Fan, Z. China Agrochem 2012, 1, 31.
- 28Yang, H. H.; Zhu, C.; Cui, C.; Li, J. Q.; Zhao, W. G.; Liu, X. H. Res Chem Intermed 2017, 43, 2377.
