Page 177 - 《精细化工》2022年第10期

第 10 期 毛明珍，等: 含硫吡唑-4-酰胺类衍生物的设计、合成与生物活性 ·2111·

目标化合物Ⅻa~k 的离体抑菌活性测试结果表 evaluation of novel N-pyridylpyrazolecarboxamides containing amino
明，在质量浓度为 50 mg/L 时，部分目标化合物对 acid methyl ester and their analogues[J]. Journal of Agricultural and
Food Chemistry, 2014, 62(7): 1536-1542.
油菜菌核、苹果轮纹、番茄早疫、小麦赤霉等病菌 [8] WU J, SONG B A, HU D Y, et al. Design, synthesis and insecticidal
表现出中等的抑菌活性。其中，化合物Ⅻf 和Ⅻg 对 activities of novel pyrazole amides containing hydrazone substructures
[J]. Pest Management Science, 2012, 68(5): 801-810.
番茄早疫病菌的抑菌率分别为 65.2%和 67.1%，高 [9] WU C C, YU X B, WANG B L, et al. Synthesis, insecticidal evaluation,
于对照药百菌清。可见，对于番茄早疫病菌抑菌活 and 3D-QASR of novel anthranilic diamide derivatives containing
N-arylpyrrole as potential ryanodine receptor activators[J]. Journal of
性，目标化合物吡唑环 5-取代基为 H 的活性高于氨
Agricultural and Food Chemistry, 2020, 68(35): 9319-9328.
基和 Br。目标化合物Ⅻa 对小麦赤霉病菌和Ⅻe 对油 [10] LI F Y, WANG Y H, LIU J B, et al. Synthesis, insecticidal evaluation
菜菌核病菌抑菌率均为 50.0%，但低于对照药百菌 and mode of action of novel anthranilic diamide derivatives containing
sulfur moiety as potential ryanodine receptor activators[J]. Bioorganic
清。目标化合物对马铃薯晚疫病菌表现出较差的抑 & Medicinal Chemistry, 2019, 27(5): 769-776.
菌活性，抑菌率均≤31.8%。将吡唑 3-硫甲基氧化 [11] WANG B L, ZHU H W, LI Z M, et al. One-pot synthesis, structure
and structure-activity relationship of novel bioactive diphenyl/diethyl
为 3-砜甲基，并没有提高目标化合物的抑菌活性。
[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl](arylamino)
methylphosphonates[J]. Pest Management Science, 2019, 75(12):
3 结论 7273-7281.
[12] ZHAO Y Y, LI G, LI H G, et al. Synthesis, insecticidal activities, and
（1）本文报道了一种合成 N-吡啶基吡唑结构 structure-activity relationship of phenylpyrazole derivatives containing
a fluoro-substituted benzene moiety[J]. Journal of Agricultural and
新方法，在此基础上设计、合成一系列含硫结构的 Food Chemistry, 2020, 68(40): 11282-11289.
N-吡啶基吡唑-4-酰胺类衍生物，目标化合物结构经 [13] ZHAO Q Q, SUN R F, LIU Y X, et al. Synthesis and insecticidal
1 HNMR、 CNMR、有机元素分析仪或高分辨质谱 activity studies of novel phenylpyrazole derivatives containing arylimine
13
or carbimidate moiety[J]. Bioorganic & Medicinal Chemistry, 2019,
仪确证。 27(21): 115092-115098.
（2）生物活性测试结果表明，目标化合物在质 [14] LOSO M R, NUGENT B M, HUANG J X, et al. Preparation of
insecticidal N-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines:
量浓度 200 mg/L 时，对东方黏虫具有中等杀虫活 WO2007095229A2[P]. 2007-08-23.
性，但低于氯虫酰胺。将吡唑环上羧基的位置由 5 [15] FENG M H, TANG B Q, LIANG S H, et al. Sulfur containing
scaffolds in drugs: Synthesis and application in medicinal
位改变为 4 位，目标化合物对东方黏虫杀虫活性大
chemistry[J]. Current Topics in Medicinal Chemistry, 2016, 16(11):
幅下降，因此，吡唑环上 5 位取代羧基结构对杀虫 1200-1216.
活性保持很重要。 [16] XU Z L (许忠良), TIAN S (田帅), LIU C F (刘春风), et al. Preparation
of 3,5-dihalobenzenecarbothioamides as pesticides: CN103130770A[P].
（3）测试了目标化合物在质量浓度 50 mg/L 时 2013-06-05.
对 5 种真菌的离体杀菌活性。其中，化合物Ⅻf 和Ⅻg [17] WU S (吴珊), LIU Y (刘莹), SHEN H (沈浩), et al. Agricultural
insecticidal composition containing thiotraniliprole and cyhalothrin
（吡唑环 5-取代基为 H）对番茄早疫病菌显示了良
and application thereof in preventing and treating vegetable lepidopteran
好的抑菌活性，高于对照药百菌清。进一步的结构 pests: CN 112715559A[P]. 2021-04-30.
优化还在进行中。 [18] NATSUHARA K, NISHIMURA S. Harmful organism control
composition: WO2008129967A1[P]. 2008-10-30.
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