Fungicidal activity of new 5-arylazo-7-nitro-8-hydroxyquinolines

I. Ustinov, I. Shakhkeldyan, Y. Atroshchenko, Anastasia V. Glazunova, Georgy V. Pescov, K. I. Kobrakov
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Abstract

Currently, agricultural production is impossible without the use of chemical plant protection products, so the search for new effective fungicides is an important and urgent task. A significant part of the systemic fungicides and antimycotics used today are azole derivatives. Research conducted at the Department of Chemistry is devoted to the analysis of the fungicidal and biological activity of substances of various classes of organic compounds, including derivatives of azoles. Previously published data on the fungicidal activity of 2-methyl-5-nitrobenzoxazole and its derivatives showed that 2-methyl-5-nitrobenzoxazole shows the highest fungicidal activity for all types of fungal cultures used in the study. The second nitro group introduced into the 2-methyl-5-nitrobenzoxazole molecule reduces fungitoxicity by 1.5-2 times. Replacing the methyl group with phenyl significantly reduces the fungicidal activity. In continuation of these studies, tests of 5-(4'-chlorophenylazo)-7-nitro-8-hydroxyquinoline, 5-(3',5'-dimethoxyphenylazo)-7-nitro-8-hydroxyquinoline and 5-(3'-methyl-4'-nitrophenylazo)-7-nitro-8-hydroxyqui-noline with respect to V. inaequalis, the causative agent of apple scab, R. solani, the causative agent of rhi-zoctonia, F. oxysporum, F. moniliforme, causative agents of cereal crops, B. sorokiniana – causative agent of root rot and S. sclerotiorum – causative agent of white rot. The radial growth of mycelium was determined according to the method developed by NIITEKHIM, according to which the fungal cultures were sown in nutrient media with the addition of the studied substan-ces. In parallel, a control experiment was conducted in the aquatic environment. The growth of mycelia was controlled by measurements on days 3, 6 and 9. The percentage of inhibition of fungal growth was calculated using the Abbott formula. Analysis of the experimental data demonstrates a higher fungicidal activity of 5-(3',5'-dimethoxy-phenylazo)-7-nitro-8-hydroxyquinoline compared with other azoquinolines for all types of fungal cultures used in the study.
新型5-芳基偶氮-7-硝基-8-羟基喹啉的杀真菌活性
目前,农业生产离不开化学植保产品的使用,因此寻找新型有效的杀菌剂是一项重要而紧迫的任务。目前使用的系统杀菌剂和抗真菌药中有很大一部分是唑衍生物。化学系的研究工作主要是分析各类有机化合物(包括唑类化合物的衍生物)的杀真菌和生物活性。先前发表的关于2-甲基-5-硝基苯并恶唑及其衍生物的杀真菌活性的数据表明,2-甲基-5-硝基苯并恶唑在研究中使用的所有类型的真菌培养物中显示出最高的杀真菌活性。在2-甲基-5-硝基苯并恶唑分子中引入第二个硝基,使真菌毒性降低1.5-2倍。用苯基取代甲基显著降低了杀真菌活性。在这些研究的继续,5 -(4'-氯苯偶氮)-7-硝基-8-羟基喹啉、5-(3',5'-二甲氧基苯基偶氮)-7-硝基-8-羟基喹啉和5-(3'-甲基-4'-硝基苯基偶氮)-7-硝基-8-羟基-喹啉对不平等弧菌(苹果疮皮病的病原体)、小麦侵染病菌、尖孢镰刀菌、单孢镰刀菌的病原体)的影响,根腐病病原B. sorokiniana和白腐病病原S. sclerotiorum根据NIITEKHIM开发的方法测定菌丝体的径向生长,根据该方法,在添加研究物质的营养培养基中播种真菌培养物。同时,在水生环境中进行了对照实验。在第3、6、9天测定菌丝生长情况。用雅培公式计算真菌生长抑制率。实验数据分析表明,5 -(3′,5′-二甲氧基-苯基偶氮)-7-硝基-8-羟基喹啉与其他偶氮喹啉相比,对研究中使用的所有类型的真菌培养物具有更高的杀真菌活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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