Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole

doi:10.1007/s40242-016-5284-6

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (1): 49-54.doi: 10.1007/s40242-016-5284-6

Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole

WU Zhilin, DING Na, LIN Ding, HU Aixi, YE Jiao, LI Guoxi

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

收稿日期:2015-07-17 修回日期:2015-08-24 出版日期:2016-02-01 发布日期:2015-10-19
通讯作者: HU Aixi E-mail:axhu@hnu.edu.cn
基金资助:
Supported by the National Key Technology R&D Program of China(No.2011BAE06B01).

Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole

WU Zhilin, DING Na, LIN Ding, HU Aixi, YE Jiao, LI Guoxi

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

Received:2015-07-17 Revised:2015-08-24 Online:2016-02-01 Published:2015-10-19
Contact: HU Aixi E-mail:axhu@hnu.edu.cn
Supported by:
Supported by the National Key Technology R&D Program of China(No.2011BAE06B01).

摘要/Abstract

摘要：

A series of novel thiazole Schiff base derivatives containing benzo[d][1,3]dioxole moiety was designed, synthesized and screened for their fungicidal activities. The preliminary results demonstrated that compounds 6p, 6q and 6r possessed potent activities against Phytophthora infestans, Pyricularia oryzae and Septoria tritici in vitro. Compounds 6d and 6r exhibited remarkable activities against Botrytis cinerea(whole plant) and Phytophthora infestans(leaf disk) respectively in vivo, which were identified as the most promising candidates for further study and could be used as possible lead compounds for developing new fungicides.

关键词: Thiazole, Schiff base, Benzo[d][1,3]dioxole, Fungicidal activity

Abstract:

Key words: Thiazole, Schiff base, Benzo[d][1,3]dioxole, Fungicidal activity

WU Zhilin, DING Na, LIN Ding, HU Aixi, YE Jiao, LI Guoxi. Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole[J]. 高等学校化学研究, 2016, 32(1): 49-54.

WU Zhilin, DING Na, LIN Ding, HU Aixi, YE Jiao, LI Guoxi. Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole[J]. Chemical Research in Chinese Universities, 2016, 32(1): 49-54.

参考文献

[1] Owen W. J., Sullenberger M. T., Loso M. R., Meyer K. G., Slanec T. J., Pest. Manag. Sci., 2015, 71, 83
[2] Al-Ani I., Zimmermann S., Reichling J., Wink M., Phytomedicine, 2015, 22, 245
[3] Wu C. C., Wu C. L., Huang S. L., Chang H. T., Wood Sci. Technol., 2011, 46, 737
[4] Li X., Ma S., Eur. J. Med. Chem., 2015, 95, 1
[5] Ayati A., Emami S., Asadipour A., Shafiee A., Foroumadi A., Eur. J. Med. Chem., 2015, 97, 699
[6] Siddiqui N., Arshad M. F., Ahsan W., Alam M. S., Int. J. Pharm. Sci. Drug. Res., 2009, 1, 136
[7] Peng J. M., Li W., Shen K., Huo S. F., Ye J., Hu A. X., Chem. J. Chinese Universities, 2013, 34(7), 1646
[8] Luo X. F., Hu A. X., Wang Y., Ye J., Wang X., G., Ou X. M., Chem. J. Chinese Universities, 2011, 32(12), 2800
[9] Altintop M. D., Ozdemir A., Turan-Zitouni G., Ilgin S., Atli O., De-mirel R., Kaplancikli Z. A., Eur. J. Med. Chem., 2015, 92, 342
[10] Amnerkar N. D., Bhongade B. A., Bhusari K. P., Arab. J. Chem., 2015, 8, 545
[11] Farghaly T. A., Abdallah M. A., Masaret G. S., Muhammad Z. A., Eur. J. Med. Chem., 2015, 97, 320
[12] Bharti S. K., Nath G., Tilak R., Singh S. K., Eur. J. Med. Chem., 2010, 45, 651
[13] Aboul-Fadl T., Bin-Jubair F. A., Aboul-Wafa O., Eur. J. Med. Chem., 2010, 45, 4578
[14] da Silva C. M., da Silva D. L., Modolo L. V., Alves R. B., de Resende M. A., Martins C. V. B., de Fátima Â., J. Adv. Res., 2011, 2, 1
[15] Break M. K., Tahir M. I., Crouse K. A., Khoo T. J., Bioinorg. Chem. Appl., 2013, 2013, 1
[16] Prakash C. R., Raja S., J. Saudi. Chem. Soc., 2013, 17, 337
[17] Bohm H. J., Flohr A., Stahl M., Drug Discov. Today Technol., 2004, 1, 217
[18] Vainio M. J., Kogej T., Raubacher F., Sadowsk J., J. Chem. Inf. Model., 2013, 53, 1825
[19] Brown N., Mol. Inform., 2014, 33, 458
[20] Jones G., Stanforth S. P., Organic Reactions, John Wiley & Sons, New Jersey, 1997, 1
[21] Lin C. K., Lu T. J., Tetrahedron, 2010, 66, 9688
[22] Wang Y., Hu A. X., Cao G., Li G. X., Zhang J. Y, Xia L., Ou X. M., Xu J., Chin. J. Org. Chem., 2008, 28, 443
[23] Powell S., Wasserman W. J., J. Am. Chem. Soc., 1957, 79, 1934
[24] Hu A. X., Qin Z., Chen P., Ye J., Chin. J. Org. Chem., 2010, 30, 923
[25] Winter C., Rheinheimer J., Wolf A., Terteryan V., Poonoth M., Wiebe C., Kremzow-Graw D., Röhl F., Rohrer S. G., Wieja A., Strobilurin Type Compounds for Combating Phytopathogenic Fungi, WO 2014202703 A1, 2014
[26] Gewehr M., Stierl R., Niedenbruck M., Hunger U., Fungicidal Mixtures, US 20080045414 A1, 2008
[27] Ye J., Qiu S. Y., Hu A. X., Peng J. M., Qin Z., Chem. Res. Chinese Uni-versities, 2014, 30(1), 49
[28] Goswami S., Kaur R., Nagrale D. T., J. Appl. Nat. Sci., 2012, 4, 264
[29] Binks P. R., Robson G. D., Goosey M. W., Trinci A. P. J., J. Gen. Mi-crobiol., 1993, 139, 1371
[30] Tvaruek L., Horáková P., Ji L., Acta Agrobot., 2005, 58, 79

Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole

Synthesis and Fungicidal Activity of Some Novel Thiazole Schiff Bases Derived from Benzo[d][1,3]dioxole

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