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Design, synthesis and herbicidal activity of novel cyclohexanedione derivations containing pyrazole and pyridine groups as potential HPPD inhibitors

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Abstract

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27; HPPD) is one of the important target enzymes in the development of herbicides. To discover novel HPPD inhibitors with unique molecular, 39 cyclohexanedione derivations containing pyrazole and pyridine groups were designed and synthesized. The preliminary herbicidal activity test results showed that some compounds had obvious inhibitory effects on monocotyledon and dicotyledonous weeds. The herbicidal spectrums of the highly active compounds were further determined, and the compound G31 exhibited the best inhibitory rate over 90% against Plantago depressa Willd and Capsella bursa-pastoris at the dosages of 75.0 and 37.5 g ai/ha, which is comparable to the control herbicide mesotrione. Moreover, compound G31 showed excellent crop safety, with less than or equal to 10% injury rates to corn, sorghum, soybean and cotton at a dosage of 225 g ai/ha. Molecular docking and molecular dynamics simulation analysis revealed that the compound G31 could stably bind to Arabidopsis thaliana HPPD (AtHPPD). This study indicated that the compound G31 could be used as a lead molecular structure for the development of novel HPPD inhibitors, which provided an idea for the design of new herbicides with unique molecular scaffold.

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Acknowledgements

The authors gratefully acknowledge the grants from Fundamental Research Funds for the Central Universities of China (No. KYTZ201604) and Student Innovation Research and Entrepreneurship Training of Nanjing Agricultural University (No. 202223XX439).

Funding

Funding was provided by Fundamental Research Funds for the Central Universities of China (Grant No. KYTZ201604) and Student Innovation Research and Entrepreneurship Training of Nanjing Agricultural University (Grant No. 202223XX439).

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Authors and Affiliations

  1. College of Sciences, Nanjing Agricultural University, Nanjing, 210095, China

    Shuai-Tao Hou, Ling Han, Wen-Rui Li, Guang-Yu Dai, Yu Liu, Ai-Min Lu, Chun-Long Yang & Min Chen

  2. Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing, 210095, China

    Shuai-Tao Hou, Yu Liu, Ai-Min Lu, Chun-Long Yang & Min Chen

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Contributions

H.S.T and H.L wrote the main manuscript text. L.W.R and D.G.Y prepared figures 1-3. L.Y and L.A.M prepared figures 8-9. Y.C.L and C.M participated in the revision of the manuscript. All authors reviewed the manuscript.

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Appendix A

Appendix A

The physical and spectroscopic data, crystal structure information and molecular docking related information of title compounds are provided in the Supporting Information. The copies of corresponding 1H NMR, 13C NMR, and HRMS spectrograms are also presented in the Supporting Information.

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Hou, ST., Han, L., Li, WR. et al. Design, synthesis and herbicidal activity of novel cyclohexanedione derivations containing pyrazole and pyridine groups as potential HPPD inhibitors. Mol Divers (2024). https://doi.org/10.1007/s11030-024-10836-6

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