Synthesis and fungicidal activity of 2-methylalkyl isonicotinates and nicotinates
Synthesis and fungicidal activity of 2-methylalkyl isonicotinates and nicotinates
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DOI：
10.1007/s00044-016-1768-7
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发表时间：
2017-03-01
影响因子：
2.6
通讯作者：
Michalczyk, Alicja
中科院分区：
文献类型：
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作者：
Huras, Bogumila;Zakrzewski, Jerzy;Michalczyk, Alicja
2-甲基庚基异烟酸酯的同系物和类似物(从链霉菌中分离出的新的天然抗真菌和抗菌抗生素。2-甲基烷基异烟酸酯4和烟酸酯5，并对映体富含R和S异构体，得到2-甲基戊基异烟酸酯和烟酸酯。对化合物的抑菌活性进行了评价。烟酸类化合物5a-c对植物病原真菌：枯萎病菌、恶疫霉菌、立枯丝核菌有明显的抑制作用。富含对映体的化合物的活性与外消旋化合物的活性相当。对映体富集型R和S异构体的抑菌活性无显著差异。所研究的化合物及其草酸盐已被证明对由真菌物种Ascosphaera apis引起的白纹伊蚊疾病具有活性。烟酸类化合物5a、5b和草酸类化合物5a-c对API的抑制活性高于草酸类物质。特别是2-甲基丁基烟酸酯5a和2-甲基戊基烟酸酯草酸盐5b的活性更高。
Homologs and analogs of 2-methylheptyl isonicotinate (new, natural antifungal and antibacterial antibiotic isolated from Streptomyces sp. 201): racemic 2-methylalkyl isonicotinates 4 and nicotinates 5 and enantiomerically enriched in the R and S isomers, 2-methylpentyl isonicotinate and nicotinate were obtained. Fungistatic activity of the compounds was evaluated. Nicotinates 5a-c show significant activity against phytopathogenic fungi: Fusarium culmorum, Phytophthora cactorum, Rhizoctonia solani. The activity of the enantiomerically enriched compounds was comparable to the activity of racemic ones. There was no significant difference in fungistatic activity between the enantiomerically enriched R and S isomers. Investigated compounds and their oxalates have proven to be active against chalkbrood disease caused by fungal species Ascosphaera apis. The activity of the nicotinates 5a and 5b and oxalates 5a-c against Ascosphaera apis was higher than the activity of oxalic acid itself. Especially high activity was shown for 2-methylbutyl nicotinate 5a and oxalate of 2-methylpentyl nicotinate 5b.Graphical abstract[GRAPHICS].