Abstract
Several new 1,3,4-oxadiazole derivatives containing a pyrazole ring were designed and synthesized from ethyl acetoacetate and triethyl orthoformate as starting materials via multi-step reactions. The compound structures were confirmed by melting point, 1H NMR and HRMS. They were evaluated for fungicidal and herbicidal activities. Four of the compounds exhibited moderate fungicidal activity against Colletotrichum species. Most of the compounds had moderate-to-good activity as a herbicide.
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S.H. Chen, J. Yu, Q.W. Li, J.P. Zhao, D.E. Wedge, S.O. Duke, D.F. Liao, Y.H. Wang, F.R. Fronczek, I.A. Khan, W. Wang, Nat. Prod. Commun. 11, 931 (2016)
A. Nasrullaev, K. Bozorov, K. Bobakulov, J.Y. Zhao, L.F. Nie, K.K. Turgunov, B. Elmuradov, H.A. Aisa, Res. Chem. Intermed. 45, 2287 (2019)
M.M. Abdou, Z. Seferoglu, M. Fathy, T. Akitsu, M. Koketsu, R. Kellow, E. Amigues, Res. Chem. Intermed. 45, 919 (2019)
X.H. Liu, Q. Wang, Z.H. Sun, D.E. Wedge, J.J. Becnel, A.S. Estep, C.X. Tan, J.Q. Weng, Pest Manag. Sci. 73, 953 (2017)
S.S. Jangam, S.B. Wankhede, S.S. Chitlange, Res. Chem. Intermed. 45, 471 (2019)
A.V. Chate, R.M. Dongre, M.K. Khaire, G.M. Bondle, J.N. Sangshetti, M. Damale, Res. Chem. Intermed. 44, 6119 (2018)
J. Safari, Z. Zarnegar, M. Sadeghi, F. Azizi, Curr. Org. Chem. 20, 2926 (2016)
D. Jaiswal, A. Mishra, P. Rai, M. Srivastava, B.P. Tripathi, S. Yadav, J. Singh, J. Singh, Res. Chem. Intermed. 44, 231 (2018)
X.H. Liu, Y.M. Fang, F. Xie, R.R. Zhang, Z.H. Shen, C.X. Tan, J.Q. Weng, T.M. Xu, H.Y. Huang, Pest Manag. Sci. 73, 1900 (2017)
X.H. Liu, L. Qiao, Z.W. Zhai, P.P. Cai, C.L. Cantrell, C.X. Tan, J.Q. Weng, L. Han, H.K. Wu, Pest Manag. Sci. 75, 2892 (2019)
R.M. Shingare, Y.S. Patil, J.N. Sangshetti, R.B. Patil, D.P. Rajani, S.D. Rajani, B.R. Madje, Res. Chem. Intermed. 44, 4437 (2018)
U. Nagarjuna, T. Rekha, T. Sreenivasulu, V. Padmavathi, A. Padmaja, Res. Chem. Intermed. 44, 4375 (2018)
V. Pogaku, R.K. Eslavath, G. Dayakar, S.S. Singh, S. Basavoju, Res. Chem. Intermed. 43, 6079 (2017)
X.M. Ding, Z.W. Zhai, L.P. Lv, Z.H. Sun, X.H. Liu, Front. Chem. Sci. Eng. 11, 379 (2017)
J.X. Mu, Z.W. Zhai, C.X. Tan, J.Q. Weng, H.K. Wu, S.O. Duke, Y.G. Zhang, X.H. Liu, J. Heterocycl. Chem. 56, 958 (2019)
N.O. Mahmoodi, S. Ghodsi, Res. Chem. Intermed. 43, 661 (2017)
G.M. Reddy, G. Sravya, G. Yuvaraja, A. Camilo, G.V. Zyryanov, J.R. Garcia, Res. Chem. Intermed. 44, 7491 (2018)
S.R. Chen, H. Wu, A.J. Li, J. Pei, L.M. Zhao, Res. Chem. Intermed. 44, 7029 (2018)
W. Zhao, Z.H. Shen, T.M. Xu, W.L. Peng, X.H. Liu, J. Heterocycl. Chem. 54, 1751 (2017)
X.H. Liu, W. Zhao, Z.H. Shen, J.H. Xing, J. Yuan, G. Yang, T.M. Xu, W.L. Peng, Bioorg. Med. Chem. Lett. 26, 3626 (2016)
W. Zhao, J.H. Xing, T.M. Xu, W.L. Peng, X.H. Liu, Front. Chem. Sci. Eng. 11, 363 (2017)
X.H. Liu, W. Zhao, Z.H. Shen, J.H. Xing, T.M. Xu, W.L. Peng, Eur. J. Med. Chem. 125, 881 (2017)
W. Zhao, Z.H. Shen, T.M. Xu, W.L. Peng, X.H. Liu, Lett. Drug Des. Discov. 14, 323 (2017)
W. Zhao, Z.H. Shen, J.H. Xing, T.M. Xu, W.L. Peng, X.H. Liu, Chin. J. Struct. Chem. 36, 423 (2017)
W. Zhao, Z.H. Shen, J.H. Xing, T.M. Xu, W.L. Peng, X.H. Liu, Chem. Pap. 71, 921 (2017)
L. Cheng, W. Zhao, Z.H. Shen, T.M. Xu, H.K. Wu, W.L. Peng, X.H. Liu, Lett. Drug Des. Discov. 16, 29 (2019)
L. Cheng, Z.H. Shen, T.M. Xu, C.X. Tan, J.Q. Weng, L. Han, W.L. Peng, X.H. Liu, J. Heterocycl. Chem. 55, 946 (2018)
X.H. Liu, C.X. Tan, J.Q. Weng, Phosphorus Sulfur Silicon Relat. Elem. 186, 558 (2011)
Z.W. Zhai, Q. Wang, Z.H. Shen, C.X. Tan, J.Q. Weng, X.H. Liu, Chin. J. Org. Chem. 37, 232 (2017)
N.B. Sun, Z.W. Zhai, Z.H. Shen, J.Q. Weng, C.X. Tan, X.H. Liu, L. Han, Chin. J. Struct. Chem. 36, 1667 (2017)
N.B. Sun, Z.H. Shen, Z.W. Zhai, L. Han, J.Q. Weng, C.X. Tan, X.H. Liu, Chin. J. Org. Chem. 37, 2705 (2017)
Z.H. Shen, Z.W. Zhai, Z.H. Sun, J.Q. Weng, C.X. Tan, X.H. Liu, Chin. J. Struct. Chem. 36, 1137 (2017)
H. Wang, Z.W. Zhai, Y.X. Shi, C.X. Tan, J.Q. Weng, L. Han, B.J. Li, X.H. Liu, J. Mol. Struct. 1171, 631 (2017)
T. Jin, Z.W. Zhai, L. Han, J.Q. Weng, C.X. Tan, X.H. Liu, Chin. J. Struct. Chem. 37, 1259 (2018)
Z.H. Shen, Y.X. Shi, M.Y. Yang, Z.H. Sun, J.Q. Weng, C.X. Tan, X.H. Liu, B.J. Li, W.G. Zhao, Chin. J. Struct. Chem. 35, 457 (2016)
N.B. Sun, Z.W. Zhai, J.Y. Tong, P.P. Cai, F.Y. He, L. Han, X.H. Liu, Chin. J. Struct. Chem. 37, 1259 (2019)
H. Wang, Z.W. Zhai, Y.X. Shi, C.X. Tan, J.Q. Weng, L. Han, B.J. Li, X.H. Liu, Lett. Drug Des. Discov. 16, 785 (2019)
J.J. Shi, G.H. Ren, N.J. Wu, J.Q. Weng, T.M. Xu, X.H. Liu, C.X. Tan, Chin. Chem. Lett. 28, 1727 (2017)
Y. Zhang, X.H. Liu, Y.Z. Zhan, L.Y. Zhang, Z.M. Li, Y.H. Li, X. Zhang, B.L. Wang, Bioorg. Med. Chem. Lett. 26, 4661 (2016)
X.H. Gan, D.Y. Hu, P. Li, J. Wu, X.W. Chen, W. Xue, B.A. Song, Pest Manag. Sci. 72, 534 (2016)
G.X. Sun, Y.X. Shi, Z.H. Sun, M.Y. Yang, H.K. Wu, J.Q. Weng, C.X. Tan, X.H. Liu, B.J. Li, Y.G. Zhang, Lett. Drug Des. Discov. 11, 1119 (2014)
C.V. Maftei, E. Fodor, P.G. Jones, M. Freytag, M.H. Franz, G. Kelter, H.H. Fiebig, M. Tamm, I. Neda, Eur. J. Med. Chem. 101, 431 (2016)
X.H. Liu, Z.W. Zhai, X.Y. Xu, M.Y. Yang, Z.H. Sun, J.Q. Weng, C.X. Tan, J. Chen, Bioorg. Med. Chem. Lett. 25, 5524 (2015)
M.Y. Yang, Z.W. Zhai, Z.H. Sun, S.J. Yu, X.H. Liu, J.Q. Weng, C.X. Tan, W.G. Zhao, J. Chem. Res. 39, 521 (2015)
X.H. Liu, Z.H. Sun, M.Y. Yang, C.X. Tan, J.Q. Weng, Y.G. Zhang, Y. Ma, Chem. Biol. Drug Des. 84, 342 (2014)
Z.W. Zhai, M.Y. Yang, Z.H. Sun, X.H. Liu, J.Q. Weng, C.X. Tan, J. Chem. Res. 39, 340 (2015)
L.J. Zhang, M.Y. Yang, Z.H. Sun, C.X. Tan, J.Q. Weng, H.K. Wu, X.H. Liu, Lett Drug Des Discov. 11, 1107 (2014)
X.H. Liu, J.Q. Weng, B.L. Wang, Y.H. Li, C.X. Tan, Z.M. Li, Res. Chem. Intermed. 40, 2605 (2014)
S.L. Yan, M.Y. Yang, Z.H. Sun, L.J. Min, C.X. Tan, J.Q. Weng, H.K. Wu, X.H. Liu, Lett. Drug Des. Discov. 11, 940 (2014)
J.Q. Weng, L. Wang, X.H. Liu, J. Chem. Soc. Pak. 34, 1248 (2012)
X.H. Liu, X.Y. Xu, C.X. Tan, J.Q. Weng, J.H. Xin, J. Chen, Pest Manag. Sci. 71, 292 (2015)
Z.H. Shen, Z.H. Sun, J.J. Becnel, A. Estep, D.E. Wedge, C.X. Tan, J.Q. Weng, L. Han, X.H. Liu, Lett. Drug Des. Discov. 15, 951 (2018)
X.H. Liu, W.G. Zhao, B.L. Wang, Z.M. Li, Res. Chem. Intermed. 38, 1999 (2012)
X.H. Liu, L. Pan, J.Q. Weng, C.X. Tan, Y.H. Li, B.L. Wang, Z.M. Li, Mol. Divers. 16, 251 (2012)
X.H. Liu, L. Pan, C.X. Tan, J.Q. Weng, B.L. Wang, Z.M. Li, Pestic. Biochem. Physiol. 101, 143 (2011)
M.M.G. El-Din, M.I. El-Gamal, M.S. Abdel-Maksoud, K.H. Yoo, C.H. Oh, Eur. J. Med. Chem. 90, 45 (2015)
X. Wang, M. Radwan, A. Trawneh, J. Gao, D.E. Wedge, L.H. Rosa, H.G. Cutler, S.J. Cutler, J. Agric. Food Chem. 61, 4551 (2013)
N. Tabanca, Z. Gao, B. Demirci, N. Techen, D.E. Wedge, A. Ali, B.J. Sampson, C. Werle, U.R. Bernier, I.A. Khan, K.H.C. Baser, J. Agric. Food Chem. 62, 8848 (2014)
D.E. Wedge, J.M. Kuhajek, Bull. Biochem. Biotechnol. 11, 1 (1998)
V.S. Sobolev, S.A. Neff, J.B. Gloer, S.I. Khan, N. Tabanca, D.E. Wedge, Phytochemistry 71, 2099 (2010)
M. Tsikolia, U.R. Bernier, M.R. Coy, K.C. Chalaire, J.J. Becnel, N.M. Agramonte, N. Tabanca, D.E. Wedge, G.G. Clark, K.J. Linthicum, D.R. Swale, J.R. Bloomquist, Pestic. Biochem. Physiol. 107, 138 (2013)
M.M. Radwan, N. Tabanca, D.E. Wedge, A.H. Tarawneh, S.J. Cutler, Fitoterapia 99, 341 (2014)
F.E. Dayan, J.G. Romagni, S.O. Duke, J. Chem. Ecol. 26, 2079 (2000)
S. Pradhan, F.J. Flores, H. Melouk, N.R. Walker, J.E. Molineras, C.D. Garzon, Am. Chem. Soc. Symp. Ser. 1249, 121 (2017)
Acknowledgements
This work was funded by Zhejiang Provincial Natural Science Foundation of China (No. LY19C140002), Research Fund of Department of Education of Zhejiang Province (Y201941832) and the Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Grant No. 2018GDGP0104.
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Yu, W., Zhai, ZW., Wedge, D.E. et al. Synthesis and biological activity of novel 1,3,4-oxadiazole derivatives containing a pyrazole moiety. Res Chem Intermed 45, 5989–6001 (2019). https://doi.org/10.1007/s11164-019-04015-8
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DOI: https://doi.org/10.1007/s11164-019-04015-8