Chinese Journal of Organic Chemistry >
Synthesis and Nematicidal Activity of Novel 1,3,4-Oxadiazole (Thiadiazole) Thioether Derivatives Containing Trifluorobuten Moiety
Received date: 2017-03-13
Revised date: 2017-04-15
Online published: 2017-05-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21672044) and the Provincial University Cooperation Plan of China (No. 20147001).
In order to explore novel leading compound with good nematicidal activity, a series of 1,3,4-oxadiazole (thiadiazole) thioether derivatives containing a trifluorobuten group were designed and synthesized, and their structures were identified by IR, 1H NMR, 13C NMR spectra, ESI-MS and elemental Anal. ysis. The results of nematicidal activity assays revealed that compounds 5a and 6b possessed excellent nematicidal activity agaist Caenorhabditis elegans in vitro after 48 h, with LC50 values of 21.92 and 44.94 μg/mL, respectively, which were superior than that of fosthiazate (72.52 μg/mL) and fluensulfone (72.96 μg/mL). Furthermore, most of compounds exhibited moderate activity against Tylenchus semipenetranss at 100 μg/mL, compound 5b showed better nematicidal activity than fosthiazate and fluensulfone after 48 h and 72 h with the values of 79.9% and 96.7%.
Chen Xuewen , Gan Xiuhai , Chen Jixiang , Chen Yongzhong , Wang Yanjiao , Hu Deyu , Song Baoan . Synthesis and Nematicidal Activity of Novel 1,3,4-Oxadiazole (Thiadiazole) Thioether Derivatives Containing Trifluorobuten Moiety[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2343 -2351 . DOI: 10.6023/cjoc201703022
[1] Caboni, P.; Saba, M.; Tocco, G.; Casu, L.; Murgia, A.; Maxia, A.; Menkissoglu-Spiroudi, U.; Ntalli, N. J. Agric. Food Chem. 2013, 61, 9784.
[2] Jang, J. Y.; Dang, Q. L.; Choi, Y. H.; Choi, G. J.; Soo, J. K.; Cha, B.; Luu, N. H.; Kim, J. C. J. Agric. Food Chem. 2015, 63, 68.
[3] Dang, Q. L.; Kim, W. K.; Nguyen, C. M.; Choi, Y. H.; Choi, G. J.; Jang, K. S.; Park, M. S.; Lim, C. H.; Luu, N. H.; Kim, J. C. J. Agric. Food Chem. 2011, 59, 11160.
[4] Chitwood, D. J. Pest Manage. Sci. 2003, 59, 748.
[5] Caboni, P.; Saba, M.; Tocco, G.; Casu, L.; Murgia, A.; Maxia, A.; Menkissoglu-Spiroudi, U.; Ntalli, N. J. Agric. Food Chem. 2013, 61, 9784.
[6] Aissani, N.; Urgeghe, P. P.; Oplos, C.; Saba, M.; Tocco, G.; Petretto, G. L.; Eloh, K.; Menkissoglu-Spiroudi, U.; Ntalli, N.; Caboni, P. J. Agric. Food Chem. 2015, 63, 6120.
[7] Lu, Q.; Shen, Q. Y.; Sun, L.; Wang, J. Y.; Song, G. H. Chin. J. Org. Chem. 2016, 36, 760(in Chinese). (陆青, 沈巧英, 孙璐, 王佳毅, 宋恭华, 有机化学, 2016, 36, 760.)
[8] Black, L. A.; Basha, A.; Kolasa, T.; Kort, M. E.; Liu, H.; McCarty, C. M.; Stewart, A. O. WO 2000024719, 2000[Chem. Abstr. 2000, 132, 321867].
[9] Jiang, Q.; Xu, W. G.; Li, H.; Chen, Z. M.; Dai, J. L.; Yang, W. S. Organo-Fluorine Ind. 2012, (3), 42(in Chinese). (蒋强, 徐卫国, 李华, 陈忠民, 戴佳亮, 杨汪松, 有机氟工业, 2012, (3), 42.)
[10] Oka, Y.; Shuker, S.; Tkachi, N. Pest Manage. Sci. 2012, 68, 268.
[11] Oka, Y.; Shuker, S.; Tkachi, N. Pest Manage. Sci, 2009, 65, 1082.
[12] Du, H. T.; Du, H. J. Chin. J. Org. Chem. 2010, 30, 137(in Chinese). (杜海堂, 杜海军, 有机化学, 2010, 30, 137.)
[13] Liu, J. C.; Wang, W. D.; He, H. W. Chin. J. Org. Chem. 2014, 34, 1447(in Chinese). (刘建超, 王卫东, 贺红武, 有机化学, 2014, 34, 1447.)
[14] Wang, B. L.; Zhu, H. W.; Li, Z. M.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483.
[15] Mo, Q. J.; Liu, L. Z.; Duan, W. G.; Cen, B.; Lin, G. S.; Chen, N. Y.; Huang, Y.; Liu, B. M. Chem. Ind. For. Prod. 2015, 35, 8.
[16] Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472(in Chinese). (石玉军, 李阳, 方源, 陈佳, 叶林玉, 葛书山, 戴红, 有机化学, 2016, 36, 2472.)
[17] Li, P.; Shi, L.; Gao, M. N.; Yang, X.; Xue, W.; Jin, L. H.; Hu, D. Y.; Song, B. A. Bioorg. Med. Chem. Lett. 2015, 25, 481.
[18] Li, P.; Shi, L.; Yang, X.; Chen, X. W.; Wu, F.; Shi, Q. C.; Xu, W. M.; He, M.; Hu, D. Y.; Song, B. A. Bioorg. Med. Chem. Lett. 2014, 24, 1677.
[19] Gan, X. H.; Hu, D. Y.; Li, P.; Wu, J.; Chen, X. W.; Xue, W.; Song, B. A. Pest Manage. Sci. 2016, 72, 534.
[20] Xu, W. M.; Yang, S.; Bhadury, P.; He, J.; He, M.; Gao, L. L.; Hu, D. Y.; Song, B. A. Pestic. Biochem. Physiol. 2011, 101, 6.
[21] Tang, X.-M. M.S. Thesis, Changchun University of Science and Technology, Shenyang, 2012(in Chinese). (唐晓明, 硕士论文, 长春理工大学, 沈阳, 2012.)
[22] Aissani, N.; Urgeghe, P. P.; Oplos, C.; Saba, M.; Tocco, G.; Petretto, G. L.; Eloh, K.; Menkissoglu-Spiroudi, U.; Ntalli, N.; Caboni, P. J. Agric. Food Chem. 2015, 63, 6120.
[23] Khan, M.; Tahir, M.; Munir, A.; Ataulah; Khan, N. H. J. Agric. Vol. 2010, 26, 271.
[24] Irshad, U.; Mukhtar, T.; Ashfaq, M.; Kayani, M. Z.; Kayani, S. B.; Hanif, M.; Aslam, S. J. Anim. Plant Sci, 2012, 4, 1014.
[25] Chawla, M. L.; Prasad, S. K. Indian J. Nematol. 1975, 4, 115.
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