Synthesis and antimicrobial activities of hexaconazole derivatives
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摘要: 为了提高己唑醇的杀菌广谱性以及杀菌活性,参考己唑醇的化学结构,以戊酰氯和取代苯为原料,经傅克酰基化、Corey-Chaykovsky环氧化反应、开环反应得到8种化合物,所有化合物均经质谱和核磁共振氢谱确证。选取常用木材腐朽菌——白腐菌(彩绒革盖菌、乳白耙齿菌)、褐腐菌(密粘褶菌、绵腐卧孔菌)和霉菌——黑曲霉作为实验菌株,采用滤纸片法研究8种目标化合物的抑菌活性。结果表明:在质量分数0.5%~2.0%范围内,除化合物A4、A5外,其余化合物对彩绒革盖菌、乳白耙齿菌、密粘褶菌、绵腐卧孔菌和黑曲霉均有一定的抑菌效果,其抑菌能力随着药液浓度的增加而增强。通过与己唑醇对照可知,化合物C3总体抑菌效果最好,并优于己唑醇;化合物C2对腐朽菌的抑菌效果优于己唑醇,对黑曲霉的抑菌效果弱于己唑醇;化合物A1、A2、A3、C1的抑菌效果均弱于己唑醇;化合物A4、A5对木材腐朽菌和霉菌几乎没有抑制作用。可见,卤素(F、Cl)对苯环2,4-二位上的取代、叔醇碳上异丁基的引入均有利于提高目标化合物的抑菌活性。Abstract: In order to improve broad-spectrum characteristics and antimicrobial activities of hexaconazole on wood-rotting fungi and moulds, valeryl chloride and substituted benzene were used as raw materials and eight compounds were synthesized by Friedel-Crafts acylation, Corey-Chaykovsky reaction and 1,2-epoxide opening reaction based on the chemical structure of hexaconazole. These compounds were confirmed by MS and 1H-NMR. Wood-rotting fungi such as white-rot fungi (Coriolus versicolor and Irpex lacteus), brown-rot fungi (Gloeophyllum trabeum and Postia placenta) and mould (Aspergillus niger) were used to test the antimicrobial activities of the compounds by filtering paper method. The results showed that the compounds had obvious antimicrobial activities on the fungi in the concentration range of 0.5%-2.0% except compounds A4 and A5,and the antimicrobial activities increased with the increase of solution concentration. The antimicroial activities of compound C3 were the best and significantly better than those of hexaconazole. The antimicrobial activities of compound C2 on wood-rotting fungi were superior to hexaconazole; however, such effects on mould were worse than those of hexaconazole. The antimicrobial effects of compounds A1, A2, A3 and C1 were not as good as hexaconazole, and compounds A4 and A5 had little inhibitory activities on wood-rotting fungi. The conclusion was that the introduction of isobutyl group in tertiary alcohol carbon,2,4-dichlorophenyl and 2,4-difluorophenyl was conducive to increasing antimicrobial activities of target compounds.
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Keywords:
- derivatives of hexaconazole /
- wood-rotting fungus /
- mould /
- antimicrobial activities
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