Synthesis, In Vitro Protoporphyrinogen Oxidase Inhibition, and Herbicidal Activity of N-(Benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones and N-(Benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones

Authors

  • Qiong-You Wu,

    1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
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  • Li-Li Jiang,

    1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
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  • Yang Zuo,

    1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
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  • Zhi-Fang Wang,

    1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
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  • Zhen Xi,

    1. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China
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  • Guang-Fu Yang

    Corresponding author
    1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China
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Abstract

Protoporphyrinogen oxidase (EC 1.3.3.4) is one of the most significant targets for a large family of herbicides. As part of our continuous efforts to search for novel protoporphyrinogen oxidase-inhibiting herbicides, N-(benzothiazol-5-yl)tetrahydroisoindole-1,3-dione was selected as a lead compound for structural optimization, leading to the syntheses of a series of novel N-(benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones (1ao) and N-(benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones (2ai). These newly prepared compounds were characterized by elemental analyses, 1H NMR, and ESI-MS, and the structures of 1h and 2h were further confirmed by X-ray diffraction analyses. The bioassays indicated that some compounds displayed comparable or higher protoporphyrinogen oxidase inhibition activities in comparison with the commercial control. Very promising, compound 2a, ethyl 2-((6-fluoro-5-(4,5,6,7-tetrahydro-1-oxo-1H-isoindol-2(3H)-yl)benzo[d]thiazol-2-yl)-sulfanyl)acetate, was recognized as the most potent candidate with Ki value of 0.0091 μm. Further greenhouse screening results demonstrated that some compounds exhibited good herbicidal activity against Chenopodium album at the dosage of 150 g/ha.

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