N-[3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-1H-吡唑-5-基]菊酰胺类化合物的合成及生物活性

为了寻求新的N-芳基吡唑类先导化合物, 用5种拟除虫菊酯类农药的活性基团——菊酸与高活性杀虫剂氟虫腈和其中间体5-氨基-3-氰基-1-(2,6-二氯-4-三氟甲基-苯基)吡唑在其氨基位置采用亚结构对接的方法合成得到了10个新的芳基吡唑菊酰胺类化合物. 经¹H NMR, ESI-MS和元素分析对化合物的结构进行了表征. 初步生物活性测定结果表明, 在37.5 mg/L浓度下, N-[3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-4-(三氟甲基亚磺酰基)-1H-吡咯-5-基]-3-(2,2-二氯乙烯基)-2,2-二甲基环丙酰胺(3b)对小菜蛾Amaranthus spinosus抑制活性达到100%, LC₅₀为15.1 mg/L. 初步雌雄大鼠急性经口毒性综合评价属中毒级, 同时还检测了2-(4-氯苯基)-N-[3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-1H-吡唑-5-基]-3-甲基丁酰胺(3i)的晶体结构.

Synthesis and Biological Activities of N-[3-Cyano-1-(2,6-dichloro- 4-trifluoromethylphenyl)-1H-pyrazol-5-yl]-chrysanthemumamide

In order to find new semicarbazide lead compounds, ten N-[1-(2,6-dicholoro-4-trifluoromethyl- phenyl)-1H-pyrazol-5-yl]-chrysanthemumamides were synthesized from five types of chrysanthemic acids with fipronil or 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-pyrazol-3-carbonitrile. The structures of all new compounds were confirmed by ¹H NMR, MS spectra and elemental analysis. At the concentration of 37.5 mg/L, compound 3b shows inhibitory activity (100%) against Plutella xylostella Linnaeus. The LC₅₀ of this compound is 15.1 mg/L. The oral acute toxicity of this compound to big male and female rats is middle. The crystal structure of 3i is also presented. The results indicate that it is rational and feasible to find new active compounds based on the connection between the active compound and the pharmacophore.