Design, synthesis, biological activity and density function theory study of pyrazole derivatives containing 1,3,4-thiadiazole moiety

doi:10.1007/s11705-017-1634-2

Front. Chem. Sci. Eng.

2017, Vol. 11

Issue (3) : 379-386 https://doi.org/10.1007/s11705-017-1634-2

RESEARCH ARTICLE

Design, synthesis, biological activity and density function theory study of pyrazole derivatives containing 1,3,4-thiadiazole moiety

Xiaoming Ding¹, Zhiwen Zhai², Luping Lv¹, Zhaohui Sun², Xinghai Liu²(

)

¹. Linjiang College, Hangzhou Vocational & Technical College, Hangzhou 310018, China
². College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China

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Abstract

A variety of pyrazole derivatives containing 1,3,4-thiadiazole moiety were synthesized under microwave irradiation, and their structures were confirmed by ¹H NMR and HRMS. They were evaluated for herbicidal and antifungal activities, and the results indicated that two compounds with a phenyl group (6a) and 4-tert-butylphenyl group (6n) possess good herbicidal activity for dicotyledon Brassica campestris and Raphanus sativus with the inhibition of 90% for root and 80%–90% for stalk at 100 ppm respectively. The structure-activity relationship of compounds 6a and 6n was also studied by density function theory method.

Keywords pyrazole 1,3,4-thiadiazole antifungal activity herbicidal activity density function theory

Corresponding Author(s): Xinghai Liu

Just Accepted Date: 07 April 2017 Online First Date: 18 May 2017 Issue Date: 23 August 2017

Cite this article:

Xiaoming Ding,Zhiwen Zhai,Luping Lv, et al. Design, synthesis, biological activity and density function theory study of pyrazole derivatives containing 1,3,4-thiadiazole moiety[J]. Front. Chem. Sci. Eng., 2017, 11(3): 379-386.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-017-1634-2
https://academic.hep.com.cn/fcse/EN/Y2017/V11/I3/379

Fig.1 Scheme 1Design strategy for pyrazole compounds with 1,3,4-thiadiazole moiety

Fig.2 Scheme 2The synthetic route of pyrazole derivatives

Tab.1 The antifungal activity of the pyrazole derivatives in vitro at 20 ppm

Tab.2 The herbicidal activity of the pyrazole derivatives at 100 ppm (%)

Fig.7 The property of compounds 6a and 6n

Tab.3 Total energy and frontier orbital energy

Fig.8 FMO of compounds 6a, 6h and penflufen (the color section represents electronic occupied)

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