Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities
Xingan Cheng,
Huiqing He,
Fangyun Dong,
Chunbao Charles Xu,
Hanhui Zhang,
Zhanmei Liu,
Xiaojing Lv,
Yuehua Wu,
Xuhong Jiang,
Xiangjing Qin
Affiliations
Xingan Cheng
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Huiqing He
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Fangyun Dong
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Chunbao Charles Xu
Department of Chemical and Biochemical Engineering, Western University, London, ON N6A 5B9, Canada
Hanhui Zhang
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Zhanmei Liu
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Xiaojing Lv
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Yuehua Wu
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Xuhong Jiang
Institute of Natural Product Chemistry, College of Chemistry and Chemical Engineering/Key Laboratory of Green Prevention and Control on Fruits and Vegetables in South China, Ministry of Agriculture and Rural Affairs/Institute of Plant Health, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China
Xiangjing Qin
CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences (CAS), Guangzhou 510301, China
Matrine is a traditional botanical pesticide with a broad-spectrum biological activity that is widely applied in agriculture. Halopyrazole groups are successfully introduced to the C13 of matrine to synthesize eight new derivatives with a yield of 78–87%. The insecticidal activity results show that the introduction of halopyrazole groups can significantly improve the insecticidal activity of matrine on Plutella xylostella, Mythimna separata and Spodoptera frugiperda with a corrected mortality rate of 100%, which is 25–65% higher than matrine. The fungicidal activity results indicate that derivatives have a high inhibitory effect on Ceratobasidium cornigerum, Cibberella sanbinetti, Gibberrlla zeae and Collectot tichum gloeosporioides. Thereinto, 4-Cl-Pyr-Mat has the best result, with an inhibition rate of 23–33% higher than that of matrine. Therefore, the introduction of halogenated pyrazole groups can improve the agricultural activity of matrine.
