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Synthesis, crystal structure, herbicidal activity and mode of action of new cyclopropane-1,1-dicarboxylic acid analogues.
Min, Li-Jing; Shen, Zhong-Hua; Bajsa-Hirschel, Joanna; Cantrell, Charles L; Han, Liang; Hua, Xue-Wen; Liu, Xing-Hai; Duke, Stephen O.
Afiliación
  • Min LJ; College of Life Science, Key Laboratory of Vector Biology and Pathogen Control of Zhejiang Province, Huzhou University, Huzhou, 313000, Zhejiang, China.
  • Shen ZH; College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, Zhejiang, China.
  • Bajsa-Hirschel J; Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 1848, MS 38677, USA.
  • Cantrell CL; Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 1848, MS 38677, USA.
  • Han L; College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, Zhejiang, China.
  • Hua XW; College of Agriculture, Liaocheng University, Liaocheng, Shandong 252000, China.
  • Liu XH; College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, Zhejiang, China. Electronic address: xhliu@zjut.edu.cn.
  • Duke SO; National Center for Natural Product Research, School of Pharmacy, University of Mississippi, P.O. Box 1848, MS, 38677, USA. Electronic address: sduke@olemiss.edu.
Pestic Biochem Physiol ; 188: 105228, 2022 Nov.
Article en En | MEDLINE | ID: mdl-36464348
A new series of cyclopropane-1,1-dicarboxylic (CPD) acid analogues were designed and synthesized. CPD is an inhibitor of ketol-acid reductoisomerase (KARI), an enzyme of the branched chain amino acid pathway in plants. The structures of CPD analogues were characterized by 1H NMR and HRMS. The structure of N,N'-bis(4-(tert-butyl)phenyl)cyclopropane-1,1-dicarboxamide was further elucidated by X-ray diffraction. The herbicidal activities of these compounds were tested against lettuce (Lactuca sativa) and bentgrass (Agrostis stolonifera). Most of these compounds exhibited low herbicidal activity against both plant species. Among them, N,N'-bis(2-ethylphenyl)cyclopropane-1,1-dicarboxamide displayed moderate activity against bentgrass. Inhibition of KARI activity by the CPD analogues was also assessed experimentally and by molecular docking simulation with results supporting inhibition of KARI as their mode of action. These results provide the basis for design of more effective KARI inhibitors.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Herbicidas Idioma: En Revista: Pestic Biochem Physiol Año: 2022 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Herbicidas Idioma: En Revista: Pestic Biochem Physiol Año: 2022 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos