Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs
Yueting Zhou,
Chunjuan Wang,
Fang Xin,
Xiaoqiang Han,
Jie Zhang,
Ke Sun
Affiliations
Yueting Zhou
Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, 221st Beisi Road, Shihezi 832002, China
Chunjuan Wang
Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, 221st Beisi Road, Shihezi 832002, China
Fang Xin
Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, 221st Beisi Road, Shihezi 832002, China
Xiaoqiang Han
Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, 221st Beisi Road, Shihezi 832002, China
Jie Zhang
Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Production and Construction Group, School of Chemistry and Chemical Engineering, 221st Beisi Road, Shihezi 832003, China
Ke Sun
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co., Ltd., No. 8-1 Shenliao Dong Road, Tiexi District, Shenyang 110021, China
For the first time, a novel series of tschimganin analogs were designed, synthesized, and evaluated for their insecticidal and fungicidal activities. Their structures were characterized by 1H-NMR, 13C-NMR and HRMS. Some of these compounds displayed excellent insecticidal and fungicidal activities, suggesting that they have potential to be used as bifunctional agrochemicals. Compound 3d and 3g with electron donating groups showed better inhibitory activity and growth inhibition activity towards Helicoverpa armigera (Hübner). The properties and positions of the substituents on the benzene ring have an important influence on the acaricidal activity of tschimganin analogs. Topomer comparative molecular field analysis (CoMFA) was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds against Tetranychus turkestani Ugarov et Nikolski. It was indicated that higher electronegativity was beneficial for acaricidal activity. Moreover, compound 3r having a 2-hydroxy-3,5- dinitrophenyl moiety displayed a fungicidal spectrum as broad as azoxystrobin against these phytopathogens.
