申嗪霉素羟基苯甲酸衍生物的合成及生物活性

Synthesis and biological activity of hydroxybenzoic acid derivatives of phenazine-1-carboxylic acid

[目的]为了提高申嗪霉素的生物活性。[方法]以吩嗪-1-羧酸为原料,通过亲核取代、酯水解等反应,将羟基苯甲酸结构片段引入吩嗪-1-羧酸中。[结果]设计合成了6个新的申嗪霉素羟基苯甲酸衍生物4a~4c和5a~5c。生物活性测定结果表明:在80 mg/L下,化合物5a对水稻纹枯病的抑菌率为74.54%;在160 mg/L时,化合物5a对水稻纹枯病的盆栽防效达到了61.26%;在160 mg/L下,化合物4a对水稻纹枯病的诱导抗病性效果达到了58.54%,与水杨酸活性相当。[结论]目标化合物不仅具有一定的杀菌活性,而且部分化合物还具有对水稻纹枯病的诱导抗病性,这对于绿色生物源农药申嗪霉素的研发具有十分重要的价值。

[Aims] This study aims to improve the biological activity of phenazine-1-carboxylic acid. [Methods] Phenazine-1-carboxylic acid was used as raw material to introduce the structural fragment of hydroxybenzoic acid into phenazine-1-carboxylic acid through nucleophilic substitution and ester hydrolysis. [Results] Six new hydroxybenzoic acid derivatives of phenazine-1-carboxylic acid 4 a-4 c and 5 a-5 c were designed and synthesized. The results of bioassay showed that the fungicidal rate of compound 5 a to Rhizoctonia solani was 74.54% at 80 mg/L;the effect of compound5 a to R. solani was 61.26% at 160 mg/L;at the concentration of 160 mg/L, the induced resistance of compound 4 a to R.solani was 58.54%, which was similar to that of salicylic acid. [Conclusions] The target compounds not only have certain fungicidal activity, but also some of them retain the induced resistance to R. solani, this is of great value to the research and development of the green biogenic pesticide phenazine-1-carboxylic.