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Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone 被引量:2

Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone
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摘要 Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahy- droisoindoline-1,3-dione scaffold to provide 25 compounds (1a-lu 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 Eehinochloa crus-galli at a rate of 375 g AI·ha^-1. Among them, compounds lh 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 lh 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 lh could potentially be used as a post-emergence herbicide for maize fields. Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahy- droisoindoline-1,3-dione scaffold to provide 25 compounds (1a-lu 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 Eehinochloa crus-galli at a rate of 375 g AI·ha^-1. Among them, compounds lh 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 lh 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 lh could potentially be used as a post-emergence herbicide for maize fields.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2015年第7期749-755,共7页 中国化学(英文版)
基金 This work was supported by the National Key Technologies R&D Program (No. 2011BAE06B03), and National Natural Science Foundation of China (No. 21172256).
关键词 SYNTHESIS tetrahydroisoindoline-l 3-dione benzoxazolinone protoporphyrinogen oxidase herbicidal activity synthesis, tetrahydroisoindoline-l,3-dione, benzoxazolinone, protoporphyrinogen oxidase, herbicidal activity
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