Mao Shiying, Wu Chengyu, Gao Yanqing, Hao Jin, He Xiaohua, Tao Pan, Li Jian, Shang Shibin, Song Zhanqian, Song Jie
Shaanxi Key Laboratory of Economic Plant Resources Development and Utilization, College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.
College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.
J Agric Food Chem. 2021 Jun 16;69(23):6475-6484. doi: 10.1021/acs.jafc.1c01887. Epub 2021 Jun 2.
To improve the effect of pine rosin in plant fungicides, four series of dehydroabietyl-1,3,4-thiadiazole derivatives from the natural product rosin were synthesized. Based on the evaluation of the antifungal activity against , , , and , rosin-based 1,3,4-thiadiazole compounds containing thiophene heterocycles were screened. Notably, compound [dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide] exhibited excellent antifungal property against with an EC of 0.618 mg/L, which was lower than that of the positive control carbendazim (0.649 mg/L). The antifungal activity results showed that exerted a protective effect on cucumber plants. Physiological and biochemical studies showed that the primary mechanism of action of compound on was it changed the mycelial morphology, increased the cell membrane permeability, and inhibited the synthesis of ergosterol in the mycelia. Furthermore, the quantitative structure-activity relationship studies revealed that the frontier orbital energy in the molecule had a key role in the antifungal activity through the conjugation and electrostatic interaction between compound and the receptors of the target. Thus, the present study highlighted the application of rosin-based fungicidal candidates and exploited efficient plant pesticides for sustainable crop production.
为提高松脂在植物杀菌剂中的效果，合成了四个系列源自天然产物松香的脱氢枞基-1,3,4-噻二唑衍生物。基于对针对[具体真菌名称缺失]、[具体真菌名称缺失]、[具体真菌名称缺失]和[具体真菌名称缺失]的抗真菌活性评估，筛选了含噻吩杂环的基于松香的1,3,4-噻二唑化合物。值得注意的是，化合物[脱氢枞基-(1,3,4-噻二唑-2-基)-5-硝基噻吩-2-甲酰胺]对[具体真菌名称缺失]表现出优异的抗真菌性能，其EC50为0.618 mg/L，低于阳性对照多菌灵(0.649 mg/L)。抗真菌活性结果表明，[具体真菌名称缺失]对黄瓜植株发挥了保护作用。生理生化研究表明，化合物[具体化合物名称缺失]对[具体真菌名称缺失]的主要作用机制是改变菌丝形态、增加细胞膜通透性并抑制菌丝体中麦角甾醇的合成。此外，定量构效关系研究表明，分子中的前沿轨道能量通过化合物[具体化合物名称缺失]与靶标受体之间的共轭和静电相互作用在抗真菌活性中起关键作用。因此，本研究突出了基于松香的杀真菌候选物的应用，并开发了用于可持续作物生产的高效植物农药。
