罗时燕, 陈锦彪, 林健, 田平义, 刘祈星, 周海峰. 新型含丁烯酸内酯基三氟乙基硫醚 (亚砜) 类化合物的设计、合成与杀螨活性[J]. 农药学学报, 2024, 26(2): 408-414. DOI: 10.16801/j.issn.1008-7303.2024.0011
    引用本文: 罗时燕, 陈锦彪, 林健, 田平义, 刘祈星, 周海峰. 新型含丁烯酸内酯基三氟乙基硫醚 (亚砜) 类化合物的设计、合成与杀螨活性[J]. 农药学学报, 2024, 26(2): 408-414. DOI: 10.16801/j.issn.1008-7303.2024.0011
    LUO Shiyan, CHEN Jinbiao, LIN Jian, TIAN Pingyi, LIU Qixing, ZHOU Haifeng. Design, synthesis and acaricidal activity of novel butenolide containing trifluoroethyl sulfide (sulfoxide) compounds[J]. Chinese Journal of Pesticide Science, 2024, 26(2): 408-414. DOI: 10.16801/j.issn.1008-7303.2024.0011
    Citation: LUO Shiyan, CHEN Jinbiao, LIN Jian, TIAN Pingyi, LIU Qixing, ZHOU Haifeng. Design, synthesis and acaricidal activity of novel butenolide containing trifluoroethyl sulfide (sulfoxide) compounds[J]. Chinese Journal of Pesticide Science, 2024, 26(2): 408-414. DOI: 10.16801/j.issn.1008-7303.2024.0011

    新型含丁烯酸内酯基三氟乙基硫醚 (亚砜) 类化合物的设计、合成与杀螨活性

    Design, synthesis and acaricidal activity of novel butenolide containing trifluoroethyl sulfide (sulfoxide) compounds

    • 摘要: 为寻找高活性杀螨化合物,以sulfiflumin为先导化合物,保留4-甲基-2-氟-5-(2, 2, 2-三氟乙硫基)苯胺活性基团,通过其与氯乙酰乙酸乙酯成环合成三氟乙基硫醚丁烯酸内酯的核心骨架C1,再对核心骨架进行氧化、氯代或溴代,以及将内酯环改造为硫内酯环及二硫代酮酯环得到C2~C8 7个化合物,采用 1H NMR、13C NMR和HRMS手段对其结构进行了表征。生物活性测试数据表明,目标化合物在100 mg/L质量浓度下具有一定的杀螨活性,尤其是对朱砂叶螨Tetranychus cinnabarinus卵孵化的抑制活性较高 (校正孵化抑制率67%~93%);此外,化合物C3对二斑叶螨Tetranychus urticae成虫的的校正死亡率达100%。该研究可为丁烯酸内酯基三氟乙基硫醚 (亚砜) 衍生物和氟吡呋喃酮衍生物的设计和改造提供研究思路,对探究该类化合物的生物活性具有参考意义。

       

      Abstract: In order to discover new acaricides with high activity, the lead compound sulfiflumin was modified, a series of novel butenolide containing trifluoroethyl sulfide (sulfoxide) compounds were designed and synthesized. First, butenolide containing trifluoroethyl sulfide (sulfoxide) C1 as a key compound was synthesized from the highly active fragment 4-methyl-2-fluoro-5-(2,2,2-trifluoroethyl thiothionyl) aniline and ethyl chloroacetoacetate. Then C2-C8 were synthesized by oxidation, chlorination or bromination of compound C1, or replacement with thiolact- one ring and dithioketone ester ring. The target compounds were characterized by 1H NMR, 13C NMR and HRMS. Acaricidal activity showed that compounds C1-C8 had certain acaricidal activity, especially for the egg of Tetranychus cinnabarinus with 67%-93% activity. Moreover, the mortality rate of compound C3 against adults Tetranychus urticae was 100%. This work provides a guideline for the modification of butenolide containing trifluoroethyl sulfide (sulfoxide) compounds and flupyradifurone and is of reference significance for exploring biological activities.

       

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