Design,Synthesis and Herbicidal Activities of Tetrahydroisoindoline‐1,3‐dione Derivatives Containing Alkoxycarbonyl Substituted 2‐Benzoxazolinone |
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| Authors: | Hao Zhang Kechang Liu Ruiquan Liu Qibo Li Yongqiang Li Qingmin Wang Shangzhong Liu |
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| Institution: | 1. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China;2. State Key Laboratory of Elemento‐Organic Chemistry, Research Institute of Elemento‐Organic Chemistry, Nankai University, Tianjin 300071, China |
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| Abstract: | Several different alkoxycarbonyl‐substituted 2‐benzoxazolinone moieties have been incorporated into a tetrahydroisoindoline‐1,3‐dione scaffold to provide 25 compounds ( 1a – 1u and 2a – 2d ). The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X‐ray single‐crystal diffraction. Some of these compounds ( 1g , 1h , 1j , 1k ) exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus‐galli at a rate of 375 g AI·ha?1. Among them, compounds 1h and 1j displayed the best post‐emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha?1, respectively, which are superior to that of the commercial acifluorfen (44.3 g AI·ha?1). Field trials demonstrated that compound 1h exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound 1h could potentially be used as a post‐emergence herbicide for maize fields. |
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| Keywords: | synthesis tetrahydroisoindoline‐1 3‐dione benzoxazolinone protoporphyrinogen oxidase herbicidal activity |
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