古建, 李晓涵, 王桢学, 陈烨烨, 陈汐玥, 李华斌. 含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性[J]. 农药学学报, 2021, 23(4): 680-687. DOI: 10.16801/j.issn.1008-7303.2021.0071
    引用本文: 古建, 李晓涵, 王桢学, 陈烨烨, 陈汐玥, 李华斌. 含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性[J]. 农药学学报, 2021, 23(4): 680-687. DOI: 10.16801/j.issn.1008-7303.2021.0071
    GU Jian, LI Xiaohan, WANG Zhenxue, CHEN Yeye, CHEN Xiyue, LI Huabin. Synthesis and herbicidal activities of 4H-pyrazolo[3,4-d][1,2,3]triazine-4-one with bulky substituents[J]. Chinese Journal of Pesticide Science, 2021, 23(4): 680-687. DOI: 10.16801/j.issn.1008-7303.2021.0071
    Citation: GU Jian, LI Xiaohan, WANG Zhenxue, CHEN Yeye, CHEN Xiyue, LI Huabin. Synthesis and herbicidal activities of 4H-pyrazolo[3,4-d][1,2,3]triazine-4-one with bulky substituents[J]. Chinese Journal of Pesticide Science, 2021, 23(4): 680-687. DOI: 10.16801/j.issn.1008-7303.2021.0071

    含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性

    Synthesis and herbicidal activities of 4H-pyrazolo3,4-d1,2,3triazine-4-one with bulky substituents

    • 摘要: 以1-(取代)苯基-5-氨基-1H-吡唑-4-甲酸乙酯或1-叔丁基-5-氨基-1H-吡唑-4-甲酰氯和2-甲基-4-炔丙基-6-氨基-7-氟-2H-苯并b1,4-噁嗪-3(4H)-酮为初始原料,分别通过不同的合成路线,得到22个未见文献报道的含大体积取代基的吡唑并三嗪酮类化合物,所有化合物的结构均通过核磁共振氢谱(1H NMR)和高分辨质谱(HRMS)确证。初步生物活性测定结果表明:在375 g/hm2处理剂量下,大部分目标化合物表现出一定的除草活性,其中化合物 4h4i4j 对反枝苋Amaranthus retroflexus生长的抑制率接近100%。

       

      Abstract: Through different synthetic routes, 22 novel 4H-pyrazolo3,4-d1,2,3 triazine-4-ones with bulky substituents were synthesized using 1-(substituted) phenyl-5-amino-1H-pyrazole-4-formate or 1-tert-butyl-5-amino-1H-pyrazole-4-carbonyl chloride and 2-methyl-4-propargyl-6-amino-7-fluoro-2H-benzob1,4-oxazine-3(4H)-one as starting materials. Their structures were confirmed by 1H NMR and HRMS. Preliminary results showed that most of the target compounds displayed herbicidal activities at the dosage of 375 g/hm2. The inhibition rates of 4h , 4i and 4j against Amaranthus retroflexus were nearly 100%.

       

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