香茅醛肟及其烷基醚的合成及抑菌活性研究

Synthesis and Antifungal Activity of Citronellal Oxime and Its Elkyl Ethers

由香茅醛与盐酸羟胺在碳酸钠作用下反应制得香茅醛肟(2),再由香茅醛肟与溴代烷、氢氧化钠在四丁基溴化铵的作用下反应合成了4种香茅醛肟烷基醚,分别为香茅醛肟乙基醚(3a)和香茅醛肟正丙基醚(3b)、香茅醛肟正丁基醚(3c)和香茅醛肟正戊基醚(3d)。5个化合物经红外光谱(FT-IR)、核磁共振(1H NMR、13C NMR)、气质联用(GC-MS)分析表征了结构,并用菌丝生长速率法对11种植物病原真菌的抑制作用进行了测试。结构分析数据表明所用方法能合成得到5种目标化合物。在药液质量浓度为500 mg/L时,5种化合物对所用植物病原真菌均有一定的抑制作用,化合物2对水稻纹枯病菌的抑制率与百菌清一样高达100%,对辣椒菌核病菌、辣椒疫霉病菌、猕猴桃果实拟茎点霉菌、梨链格孢菌和毛竹枯梢病菌的抑制率高达100%,对油茶炭疽病菌、层出镰刀菌的抑制率也很高(≥95%),明显优于百菌清对这些病菌的抑制效果,3a对莴苣菌核病菌的抑制率高达100%,3b对葡萄炭疽病菌的抑制率为100%,3c对毛竹枯梢病菌的抑制率为87.7%,3d对莴苣菌核病菌的抑制率为96.2%,均高于同等质量浓度下百菌清对这些植物病原真菌的抑制率。

Citronellal oxime（ 2 ） was prepared from the reaction of citronellal and hydroxylamine hydrochloride under the alkaline condition provided by sodium carbonate. And then, four kinds of citronellal oxime alkyl ethers, respectively, citronellal oxime ethyl ether（ 3a ）, citronellal oxime n -propyl ether（ 3b ）, citronellal oxime n -butyl ether（ 3c ）, citronellal oxime n -penta ether（ 3d ）, were prepared from the halogenated reaction of citronellal oxime with five alkyl bromides, sodium hydroxide and the phase transfer catalyst tetrabutyl bromide ammonium. Identification and structural analysis were done by using FT-IR,NMR（ 1 H NMR, 13 C NMR） and GC-MS methods. And the antifungal activities of all compounds against eleven plant pathogenic fungi were studied by using the mycelial growth rate method. The structural analysis results showed that the method could synthesize 5 target compounds and the antifungal activity test showed that at the mass concentration of 500 mg/L, the five compounds had certain antifungal activity against the eleven tested Feleven tested plant pathogenic fungi. Among these inhibitory rate dates, the inhibition rate of compound 2 on Rhizoctonia solani reached 100%,equal to that of chlorothalonil,the inhibition rate on Sclerotinia sclerotiorum , Phytophthora capsici , Botryis phariadothide , Alternaria kikuchiana and Ceratosphaeria phyllostachydis reached 100%, the inhibition rates on Glomerella cingulata and Fusarium proliferatum also reached high inhibition rates（≥95%）,which were much higher than the inhibition abilities of chlorothalonil against these pathogens; the inhibition rate of 3a on Lettuce sclerotinia reached 100%, the inhibition rate of 3b on Colletorichum gloeosporioides reached 100%, the inhibition rate of 3c on Ceratosphaeria phyllostachydis reached 87.7% and the inhibition rate of 3d on Lettuce sclerotinia reached 96.2%,these all were higher than the inhibition rates of chlorothalonil on these pathogenic fungi at the same mass concentration.