紫苏醛基席夫碱-(硫)脲化合物的合成及生物活性

Synthesis and Biological Activities of Perillaldehyde-based Schiff Base-(thio) urea Compounds

以紫苏醛为原料,设计合成了13个未见文献报道的紫苏醛基席夫碱-(硫)脲化合物(5a^5m),通过FT-IR、~1H NMR、^(13)C NMR和ESI-MS对其结构进行了分析和表征,并测试了目标化合物的抑菌和除草活性。生物活性测试表明,在质量浓度50 mg/L下,目标化合物5f(R=p-FAr)对苹果轮纹病菌的抑制率达90.0%(接近阳性对照嘧菌酯),化合物5d(R=Ar)对番茄早疫病菌的抑制率达91.8%(接近阳性对照嘧菌酯)。在质量浓度100 mg/L下,目标化合物5c(R=环己基)、5i(R=p-CH3Ar)和5a(R=CH3)对油菜胚根生长的抑制率分别为77.6%、75.3%和67.4%(高于阳性对照丙炔氟草胺)。总体上,取代苯基硫脲类目标化合物的抑菌和除草活性优于取代苯基脲类目标化合物。

Thirteen novel perillaldehyde-based Schiff base-（thio）urea compounds （5a-5m） were designed and synthesized by using perillaldehyde as starting material. Their structures were analyzed and characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS. The results of preliminary bioassay showed that, at the mass concentration of 50 mg/L, the inhibition rate of target compound 5f （R=p-FAr） against Physalospora piricola was 90.0% （close to that of the positive control azoxystrobin）, and the inhibition rate of target compound 5d （R=Ar） against Alternaria solani was 91.8% （close to that of the positive control azoxystrobin）. Besides, at the mass concentration of 100 mg/L, the target compounds 5c （R=cyclopentyl）, 5i （R=p-CH3Ar） and 5a （R=CH3） exhibited 77.6%, 75.3% and 67.4% inhibition against the growth of rape （Brassica campestris） root, respectively （greater than positive control flumioxazin）. Furthermore, substituted phenyl thioureas showed better antifungal and herbicidal activities than substituted phenyl ureas.