单喜杰, 李海洁, 李天泽, 徐晖, 吕敏. 3-芳基-4,5-二氢异噁唑-5-甲酸环戊烷多氢菲酯类衍生物的合成与杀虫活性[J]. 农药学学报, 2022, 24(6): 1358-1366. DOI: 10.16801/j.issn.1008-7303.2022.0066
    引用本文: 单喜杰, 李海洁, 李天泽, 徐晖, 吕敏. 3-芳基-4,5-二氢异噁唑-5-甲酸环戊烷多氢菲酯类衍生物的合成与杀虫活性[J]. 农药学学报, 2022, 24(6): 1358-1366. DOI: 10.16801/j.issn.1008-7303.2022.0066
    SHAN Xijie, LI Haijie, LI Tianze, XU Hui, LYU Min. Synthesis and pesticidal activities of cyclopentanoperhydrophenanthrene 3-aryl-4,5-dihydroisoxazole-5-formate derivatives[J]. Chinese Journal of Pesticide Science, 2022, 24(6): 1358-1366. DOI: 10.16801/j.issn.1008-7303.2022.0066
    Citation: SHAN Xijie, LI Haijie, LI Tianze, XU Hui, LYU Min. Synthesis and pesticidal activities of cyclopentanoperhydrophenanthrene 3-aryl-4,5-dihydroisoxazole-5-formate derivatives[J]. Chinese Journal of Pesticide Science, 2022, 24(6): 1358-1366. DOI: 10.16801/j.issn.1008-7303.2022.0066

    3-芳基-4,5-二氢异噁唑-5-甲酸环戊烷多氢菲酯类衍生物的合成与杀虫活性

    Synthesis and pesticidal activities of cyclopentanoperhydrophenanthrene 3-aryl-4,5-dihydroisoxazole-5-formate derivatives

    • 摘要: 为了寻找具有较高杀虫活性的胆固醇衍生物,将异噁唑啉片段引入母体胆固醇( 1 )的C-3位,制备了20个新的3-芳基-4,5-二氢异噁唑-5-甲酸环戊烷多氢菲酯类衍生物 Ia~It ,并经氢谱、红外光谱和高分辨质谱确证结构。化合物 Ie (R = 3-BrPh) 对小菜蛾Plutella xyllostella幼虫具有较好的杀虫活性,其48 h LC50值为 0.940 mg/mL,是母体胆固醇 (LC50 值2.566 mg/mL) 的2.7倍;化合物 Ig (R = 3-FPh) 和 Ij (R = 4-CF3Ph) 对苹果黄蚜Aphis citricola具有较好的杀虫活性,其48 h LD50值为0.042与0.041 μg/头,是胆固醇 (LD50 值0.228 μg/头) 的5.4和5.6倍。初步构效关系表明,在苯环间位引入溴原子可提高对小菜蛾的杀虫活性;在苯环对位或间位引入氟原子、或者在对位引入三氟甲基可提高对苹果黄蚜的杀虫活性。

       

      Abstract: In order to find cholesterol derivatives with high insecticidal activities, isoxazoline fragments were introduced into the C-3 position of cholesterol ( 1 ), and twenty novel cyclopentanoperhydrophenanthrene 3-aryl-4,5-dihydroisoxazole-5-formate derivatives ( Ia - It ) containing the isoxazoline fragment were prepared. Their structures were characterized by 1H NMR, IR and HRMS. Among them, compound Ie (R = 3-Br-Ph) exhibited good insecticidal activity against Plutella xyllostella with a LC50 value of 0.940 mg/mL at 48 h, which was 2.7 times of that of 1 (LC50: 2.566 mg/mL). Compounds Ig (R = 3-F-Ph) and Ij (R = 4-CF3-Ph) showed the potent aphicidal activity against Aphis citricola with LD50 values of 0.042 and 0.041 μg/nymph at 48 h, respectively, which were 5.4 and 5.6 times of that of 1 (LD50: 0.228 μg/nymph). The preliminary study of structure-activity relationships (SARs) indicated that introduction of the bromine atom at the C-3 position of phenyl can improve the insecticidal activity against P. xyllostella; introduction of the fluorine atom at the C-3 or C-4 position of phenyl, or introduction of the CF3 at the C-4 position of phenyl can improve the aphicidal activity against A. citricola.

       

    /

    返回文章
    返回