SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 12: 2612 - 2617

DOI: https://doi.org/10.6023/cjoc201306028

Notes

Synthesis and Herbicidal Activity of New 1,3,4-Thiadizols Sulfourea Derivative

  • Sun Zhaohui ,
  • Huang Wei ,
  • Gong Yunyun ,
  • Lan Jian ,
  • Liu Xinghai ,
  • Weng Jianquan ,
  • Li Yongshu ,
  • Tan Chengxia
Expand
  • College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014

Received date: 2013-06-19

  Revised date: 2013-07-19

  Online published: 2013-08-13

Supported by

Project supported by the National Key Technologies R & D Program (No. 2011BAE06B03-01) and the Key Innovation Team of Science and Technology in Zhejiang Province (No. 2010R50018).

Fold

Abstract

To find new pesticidal lead compounds with high bioactivity, 18 acylthioureas contain 1,3,4-thiadizols were obtained by condensation between acyl isothiocyanate and 1,3,4-thiadiazols. Their structures were confirmed by 1H NMR and MS. The herbicidal activities of these compounds were evaluated. All the compounds have herbicidal activity at 200 g ai/ha. The bioassay results showed that compound 5b had 90% inhibitory effect against Echinochloa crusgalli, Setaira viridis, Digitaria sanguinalis, Amaranthus retroflexus and Eclipta prostrate at 200 g ai/ha in pre-emergence condition and 90% and 95% against Echinochloa crusgalli and Eclipta prostrate at 200 g ai/ha in post-emergence condition, respectively; and compound 5e had 100% inhibitory effect against Echinochloa crusgalli, Setaira viridis, Digitaria sanguinalis and Amaranthus retroflexus at 200 g ai/ha in post-emergence and post-emergence condition.

Key words： acyl thiourea; 1,3,4-thiadiazol; synthesis; herbicidal activity

Cite this article

Sun Zhaohui , Huang Wei , Gong Yunyun , Lan Jian , Liu Xinghai , Weng Jianquan , Li Yongshu , Tan Chengxia . Synthesis and Herbicidal Activity of New 1,3,4-Thiadizols Sulfourea Derivative[J]. Chinese Journal of Organic Chemistry, 2013 , 33(12) : 2612 -2617 . DOI: 10.6023/cjoc201306028

References

[1] Zhang, Q.-L.; Yuan, Z.-L.; Zhang, Y.-Q.; Zhu, B.-X. Acta Chim. Sinica 2012, 70, 357 (in Chinese). (张奇龙, 袁泽利, 张云黔, 朱必学, 化学学报, 2012, 70, 357.)

[2] Yao, J.-W.; He, Z.-P.; Chen, J.; Chen, D.-Q.; Sun, W.; Xu, W.-F. Chin. J. Chem. 2012, 2423.

[3] Crank, G.; Neville, M.; Ryden, R. J. Med. Chem. 1973, 16, 1024.

[4] Ramadas, K.; Suresh, G.; Janarthanan, N.; Masilamani, S. Pestic Sci. 1998, 52, 145.

[5] Che, C.; Mao, S.-F.; Mu, C.-W. Chin. J. Pestic. 2002, 4, 75 (in Chinese). (车超, 毛淑芬, 幕长炜, 农药学学报, 2002, 4, 75.)

[6] Cai, A.; Xue, S.-J.; Bian, W.-D.; Yu, S.-R. Chin. J. Org. Chem. 2008, 28, 1199 (in Chinese). (柴安, 薛思佳, 卞王东, 吁松瑞, 有机化学, 2008, 28, 1199.)

[7] Wang, T.-T.; Miao, W.-K.; Wu, S.-S.; Bing, G.-F.; Zhang, X.; Qin, Z.-F.; Yu, H.-B.; Qin, X.; Fang, J.-X. Chin. J. Chem. 2011, 29, 959.

[8] Saeed, E.; Alireza, F. Chemistry (Rajkot, India) 2005, 2, 10.

[9] Zhang, X.; Qin, Z.-L. Chin. J. Org. Chem. 2006, 26, 870 (in Chinese). (张欣, 覃章兰, 有机化学, 2006, 26, 870.)

[10] Kolavi, G.; Hegde, V.; Khazia, I. A; Gadad, P. Bioorg. Med. Chem. 2006, 14, 3069.

[11] Wang, Y.-G.; Cao, L.; Yang, J. Chem. J. Chin. Univ. 1999, 20, 1903 (in Chinese). (汪焱钢, 曹蕾, 杨军等, 高等学校化学学报, 1999, 20, 1903.)

[12] Wang, Y.-G.; Wang, Z.-Y.; Zhao, X.-J. Chin. J. Org. Chem. 2004, 24, 1606 (in Chinese). (汪焱钢, 王子云, 赵新筠, 有机化学, 2004, 24, 1606.)

[13] Terzioglu, N.; Gursoy, A. Eur. J. Med. Chem. 2003, 38, 781.

[14] Hu, G.-Q.; Zhang, Z.-Q.; Xu, Q.-T.; Huang, W.-L.; Wang, H. Acta Chim. Sinica 2004, 62, 204 (in Chinese). (胡国强, 张忠泉, 许启泰, 黄文龙, 汪海, 化学学报, 2004, 62, 204.)

[15] Song, B.-A.; Chen, C.-J.; Yang, S.; Jin, L.-H.; Xue, W.; Zhang, S.-M.; Zou, Z.-H.; Hu, D.-Y.; Liu, G. Acta Chim. Sinica 2005, 63, 1720 (in Chinese). (宋宝安, 陈才俊, 杨松, 金林红, 薛伟, 张素梅, 邹志辉, 胡德禹, 刘刚, 化学学报, 2005, 63, 1720.)

[16] Kolavi, G.; Hegde, V.; Khazia, I.A.; Gadad, P. Bioorg. Med. Chem. 2006, 14, 3069.

[17] Jatav, V.; Mishra, P.; Kashaw, S. Eur. J. Med. Chem. 2008, 43, 1945.

[18] Shi, Y.-P.; Chen, B.-Q.; Ma, J.; Liu, Y.-M.; Li, C.-W. Acta Chim. Sinica 2011, 69, 2561 (in Chinese). (史艳萍, 陈宝泉, 麻静, 刘玉明, 李彩文, 化学学报, 2011, 69, 2561.)

[19] Feng, X.-M.; Chen, S.; Huang, J.-S.; Zhang, Z.-Y. Chem. J. Chin. Univ. 1993, 14, 65 (in Chinese). (冯小明, 陈荣, 黄劲松, 张自义, 高等学校化学学报, 1993, 14, 65.)

[20] Le, Z.-G.; Ding, J.-H.; Yang, S.-J. Chem. World 2002, 366 (in Chinese). (乐长高, 丁健桦, 杨思金, 化学世界, 2002, 366.)

[21] Liu, Y.-T.; Zhou, Y.; Yin, D.-W. Spec. Petrochem. 2011, 28, 61 (in Chinese). (刘玉婷, 周英, 尹大伟, 精细石油化工, 2011, 28, 61.)

Options
Outlines

/

〈 〉