Synthesis and Herbicidal Activities of 2-[2-(4,6-Dimethoxypyrimidin-2- yloxy)phenyl]-2-(substituted aniline)acetonitrile Derivatives

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (12): 2140-2144. Previous Articles Next Articles

Notes

2-[2-(4,6-二甲氧基嘧啶-2-氧)苯基]-2-(取代苯胺)乙氰类化合物的合成及除草活性研究

李元祥^1,2，刘玉超¹，陈琼*^,1

(¹华中师范大学农药与化学生物学教育部重点实验室武汉 430079)
(²怀化学院化学化工系怀化 418008)

收稿日期:2010-03-02 修回日期:2011-08-12 发布日期:2011-08-12
通讯作者: 陈琼 E-mail:qchen@mail.ccnu.edu.cn

Synthesis and Herbicidal Activities of 2-[2-(4,6-Dimethoxypyrimidin-2- yloxy)phenyl]-2-(substituted aniline)acetonitrile Derivatives

Li Yuanxiang^1,2 Liu Yuchao¹ Chen Qiong*^,1

(¹Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079)
(²Chemistry and Chemical Engineering Department, Huaihua University, Huaihua 418008)

Received:2010-03-02 Revised:2011-08-12 Published:2011-08-12
Contact: Qiong CHEN E-mail:qchen@mail.ccnu.edu.cn

Using 2-hydroxybenzaldehyde as starting material, twelve 2-[2-(4,6-dimethoxypyrimidin- 2-yloxy)phenyl]-2-(substituted aniline)acetonitrile derivatives have been synthesized by one-pot three- component reaction of 2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde intermediate. All synthesized compounds were confirmed by ¹H NMR, MS techniques and elemental analysis. High herbicidal activities of all compounds were showed at preliminary bioassay.

Key words: 4,6-dimethoxypyrimidine, synthesis, herbicidal activity

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LI Yuan-Xiang, LIU Yu-Chao, CHEN Qiong. Synthesis and Herbicidal Activities of 2-[2-(4,6-Dimethoxypyrimidin-2- yloxy)phenyl]-2-(substituted aniline)acetonitrile Derivatives[J]. Chin. J. Org. Chem., 2011, 31(12): 2140-2144.

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References

1 Xue, S.J.; Zou, J. S. Chemical World. 2000, 8, 399(in Chinese).

(薛思佳, 邹金山. 化学世界, 2000, 8, 399.)

2 Cao, D,F.; Zhou, J.J. Chinese Journal of Biochemistry and Molecular Biolog. 1999, 15(2), 332(in Chinese).

(曹殿芳, 周家驹. 中国生物化学与分子生物学报, 1999, 15(2), 332.)

3 Yang, G.F.; Yang, H.Z. Research of Herbicides Targeted ALS, Central China Normal University Press, Wuhan, 2002, pp. 18 (in Chinese).

(杨光富, 杨华铮. 以ALS为作用靶的超高效除草剂研究, 华中师范大学出版社, 武汉, 2002, pp. 18.)

4 Wada, N.; Kusano, S.; Toyokawa, Y. EP 321846, 1989 [Chem. Abstr. 1989, 112, 93933].

5 Tamaru, M.; Kawamura, N.; Sato, M. et al. EP 435170, 1991 [Chem. Abstr. 1991, 115, 159183].

6 Saito, Y.; Wada, N.; Kusano, S.; Miyazawa, T. et al. EP 315889, 1989 [Chem. Abstr. 1989, 111, 232852].

7 Kim, K. T.; Lee, B. B.; Joe, G. H. et al. CA 2194080, 1997 [Chem. Abstr. 1997, 127, 318973].

8 Koo, S. J.; Ahn, S. C.; Lim, J. S. et al. Pestic. Sci, 1997, 51, 109.

9 Luthy, C.; Obrecht, J. P. WO 9105781, 1991 [Chem. Abstr. 1991, 115, 183367].

10 Liun C. L. PESTICIDES, 2002, 43(9), 44(in Chinese).

(刘长令. 农药, 2002, 43(9), 44.)

11 Feng, X.;Yao, J.H.; Lü, L.; Tang, Q.H.; Fan, B.T.; Acta Chim. Sinica.2006, 64, 1097 (in Chinese).

(冯骁，姚建华，吕龙，唐庆红，范波涛，化学学报, 2006, 64, 1097.)

12 Bessard, I.; Stucky, G. EP 802193, 1997 [Chem. Abstr. 1997, 127, 358872].

13 Wen, Y. Z.; Fang, Z. H.; Liu, W. P. J. Zhejiang Univ. 2004, 5(8), 956.

14Yves, B.; Roger, C. Tetrahedron. 2000, 56, 4739.

15 Nezu, Y.; Sugiyama, K.; Kusano, S. et al. EP 223406, 1987 [Chem. Abstr. 1987, 107, 134322].

16 Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron Letters, 1995, 36(16), 2859.

17 Bisel, P.; Fondekar, K. P.; Volk, F. J. et al. Tetrahedron. 2004, 60, 10541.

18 Li,Y.X. Acta Cryst. 2009, E65, o2295.

19 Lv, L.; Chen, J.; Wang, H. et al. CN 1746161, 2006 [Chem. Abstr. 2006, 145, 124582] (in Chinese).

(吕龙, 陈杰, 王华等. CN 1746161, 2006 [Chem. Abstr. 2006, 145, 124582].)

20 Lv, L.; Lv, Q.; Tang, Q. H. et al. CN 101367766, 2009[Chem. Abstr. 2009, 150, 329828] (in Chinese).

(吕龙, 吕强, 唐庆红等. CN 101367766, 2009 [Chem. Abstr. 2009, 150, 329828].)

21 Lv, L.; Tang, Q. H.; Lv, Q. et al. CN 101367769, 2009 [Chem. Abstr. 2009, 150, 329827] (in Chinese).

(吕龙, 唐庆红, 吕强等. CN 1013677691, 2009 [Chem. Abstr. 2009, 150, 329827].)

22 Lv, L.; Lv, Q.; Tang, Q. H. et al. CN 101367798, 2009[Chem. Abstr. 2009, 150, 306666] (in Chinese).

(吕龙, 吕强, 唐庆红等. CN 101367798, 2009 [Chem. Abstr. 2009, 150, 306666].)

23 Banphavichit, V.; Mansawat, W.; Bhanthumnavin, W. et al. Tetrahedron. 2004, 60(46), 10559.

24 Li, Y. X.; Luo, Y. P.; Xi, Z. et al. J. Agric. Food Chem. 2006, 54, 9135.

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2-[2-(4,6-二甲氧基嘧啶-2-氧)苯基]-2-(取代苯胺)乙氰类化合物的合成及除草活性研究

Synthesis and Herbicidal Activities of 2-[2-(4,6-Dimethoxypyrimidin-2- yloxy)phenyl]-2-(substituted aniline)acetonitrile Derivatives

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