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Paper | Regular issue | Vol 92, No. 5, 2016, pp.829-843
Published online, 14th March, 2016
DOI: 10.3987/COM-16-13415
Synthesis, Crystal Structure and Herbicidal Activity of a Series of [1,2,4]Triazolo[1,5-a]pyrimidine-2-sulfonamide Compounds

Yi-Chao Ma, Ying-Hui Yu, Guang-Feng Hou,* Ji-Han Huang, and Jin-Sheng Gao*

*Engineering Research Center of Pesticide, Heilongjiang University, Xuefu Road 74# 150080, China

Abstract

With the aim of obtaining efficient, safe and environmentally friendly green herbicide, a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds (8a8f) were synthesized by reacting 2-amino-5,7-(bis-substituted)- 1,2,4-triazolo[l,5-a]pyrimidine (4a and 4b) with 2-substituted-6-trifluoromethyl- benzenesulfonyl chloride (7a7c). And their structures were characterized by 1H-NMR, 13C-NMR, HRMS, FTIR, single-crystal X-ray diffraction, elemental analysis. Moreover, their herbicidal activities against six species of weeds were evaluated. Three target compounds such as 8a, 8c and 8e, exhibited significant postemergence herbicidal activity against some common dicotyledons and monocotyledons under different concentrations. The structure and activity relationship is discussed based on the herbicidal performances of the compounds with different substituents. The investigation results indicated that the above structures could serve as lead compounds for the development of new herbicides.