1-芳基-4-吡唑-5-酰基氨基脲类化合物的合成及杀菌活性

Synthesis and Fungicidal Activities of 1-[(Un)substituted phenyl]-4-(pyrazol-5-ylcarbonyl)semicarbazide

为了寻求新的吡唑先导化合物,用4-氯-1-甲基-3-乙基-5-吡唑甲酰肼与取代苯基异氰酸酯反应得到了14个新的1-吡唑酰基-4-芳基氨基脲类化合物.经IR,1HNMR,MS和元素分析对化合物的结构进行了表征.初步生物活性实验结果表明,在500μg/mL浓度下,化合物1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-(2-甲基苯基)氨基脲(4g),1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-(2,4-二甲基苯基)氨基脲(4k)对小麦白粉病菌(Blumeriagraminis)的抑制率分别达到90%和80%;在25μg/mL浓度下,化合物1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-苯基氨基脲(4c)对黄瓜灰霉病菌(Botrytiscinerea)的抑制率达到70.1%;化合物1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-苯基氨基脲(4c)和1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-(2-硝基苯基)氨基脲(4d)对稻瘟病菌(Pyriculariaoryzae)的抑制率均达到51.3%.

In order to find new pyrazole leading compounds, 14 1-[（un）substituted phenyl]-4-（pyrazol- 5-ylcarbonyl）semicarbazide derivatives were synthesized from 4-chloro-3-ethyl-l-methyl-5-pyrazole carbonhydrazide and substituted phenylisocyanate. The structures of all the new compounds were confirmed by 1H NMR, IR, MS and elemental analysis. The preliminary bioassays indicated that, at 500 gg/mL, 1-（o-tolyl）-4-（4-chloro-3-ethyl-1-methylpyrazol-5-ylcarbonyl）semicarbazide （4g） and 1-（2,4-dimethyl- phenyl）-4-（4-chloro-3-ethyl-l-methylpyrazol-5-ylcarbonyl）semicarbazide （4k） showed inhibitory activities 90% and 80% against Blumeria graminis, respectively; and at 25 μg/mL, 4-phenyl-4-（4-chloro-3-ethyl-1- methylpyrazol-5-ylcarbonyl）semicarbazide （4e） showed inhibitory activity 70.1% against Botrytis cinerea and 1-（2-nitro-phenyl-4-（4-chloro-3-ethyl-1-methylpyrazol-5-ylcarbonyl）semicarbazide （4d） showed inhibitory activitiy 51.3% against Pyricularia oryzae.