含硫吡唑-4-酰胺类衍生物的设计、合成与生物活性

Design, synthesis and biological evaluation of novel N-pyridylpyrazole-4-carboxamides containing sulfur moiety

为寻找高生物活性的吡唑酰胺类化合物,在氯虫酰胺分子基础上,经结构优化,设计、合成一系列含硫结构的N-吡啶基吡唑-4-酰胺类衍生物,目标化合物经~1HNMR、CNMR、有机元素分析仪或高分辨质谱仪确证,并进行了初步杀虫及杀菌活性测试。结果表明,在质量浓度为200 mg/L时,目标化合物对东方黏虫具有中等杀虫活性,其中,5-溴-N-[(4-氯-2-甲基-6-甲酰基)苯基]-1-(3-氯-2-吡啶基)-3-硫甲基-1H-吡唑-4-甲酰胺杀虫活性为80%。在质量浓度为50mg/L时,部分化合物对5种病菌表现出中等的离体抑菌活性,N-[(4-氯-2-甲基-6-甲酰胺基)苯基]-1-(3-氯-2-吡啶基)-3-硫甲基-1H-吡唑-4-甲酰胺和N-[(4-氯-2-甲基-6-环丙基酰胺基)苯基]-1-(3-氯-2-吡啶基)-3-硫甲基-1H-吡唑-4-甲酰胺对番茄早疫病菌显示了良好的活性,分别为65.2%和67.1%,高于对照药百菌清。

To explore new compounds with high biological activity, a series of novel N-pyridylpyrazole-4-carboxamides containing sulfur moiety were designed and synthesized from commercial insecticide chlorantraniliprole via structural optimization. The compounds obtained were then identified by ~1HNMR,CNMR, elemental analysis analyzer or HRMS(high resolution mass spectorometer), followed by preliminary evaluations on their insecticidal and bactericidal activities. The results indicated that all the synthesized compounds showed moderate insecticidal activities against oriental armyworm(Mythimna separata) at a mass concentration of 200 mg/L, of which 5-bromo-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-1-(3-chloropyridin-2-yl)-3-(methylsulfanyl)-1H-pyrazole-4-carboxamide exhibited 80% insecticidal activity. Meanwhile, some compounds exhibited promising fungicidal activities when tested against five fungi at a mass concentration of 50 mg/L. Specifically, N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-1-(3-chloropyridin-2-yl)-3-(methylsulfanyl)-1H-pyrazole-4-carboxamide and N-[4-chloro-2-(cyclopropylcarbamoyl)-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(methylsulfanyl)-1H-pyrazole-4-carboxamide displayed a good fungicidal activity against Alternaria solani, with inhibitory rate of 65.2% and 67.1%, respectively, higher than that of positive control compound chlorothalonil.