Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties.
A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 μg/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Bao-Lei
BL
Wang
Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China.
Yan-Xia
YX
Shi
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Shu-Jun
SJ
Zhang
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Yi
Y
Ma
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Hong-Xue
HX
Wang
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Li-Yuan
LY
Zhang
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Wei
W
Wei
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Xing-Hai
XH
Liu
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China.
Yong-Hong
YH
Li
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China. Electronic address: nkzml@vip.163.com.
Zheng-Ming
ZM
Li
Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China. Electronic address: libj@mail.caas.net.cn.
Bao-Ju
BJ
Li
D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D017739:Arylsulfonic Acids / Q000737:chemistry; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship
D000577:Amides; D000935:Antifungal Agents; D017739:Arylsulfonic Acids; D006540:Herbicides; D010879:Piperazines; D000077489:Piperazine
3D-QSAR; Arylsulfonyl group; Biological activities; Piperazine derivatives; Theoretical calculation