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Discovery of Terpene-Derived Quaternary Ring Compounds Containing an Oxime Moiety as Potential Fungicides
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-02-07 , DOI: 10.1021/acs.jafc.2c07387 Tingmin Pan 1 , Jiuhui Ye 1 , Jiening Li 1 , Kuo Gui 1 , Jian Li 2 , Juntao Feng 1 , Zhiqing Ma 1 , Peng Lei 1 , Yanqing Gao 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-02-07 , DOI: 10.1021/acs.jafc.2c07387 Tingmin Pan 1 , Jiuhui Ye 1 , Jiening Li 1 , Kuo Gui 1 , Jian Li 2 , Juntao Feng 1 , Zhiqing Ma 1 , Peng Lei 1 , Yanqing Gao 1
Affiliation
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Terpene-derived quaternary ring compounds with an oxime moiety were designed and prepared to create fungicides from natural products. A preliminary assessment of their antifungal activity against seven common pathogenic fungi was conducted, and the median effective concentration (EC50) values against Rhizoctonia solani were obtained. The effects of compound 6a19 (3-bromothiophene-containing), which had an outstanding EC50 value (1.62 μg/mL), on the morphology, ultrastructure, reactive oxygen species production, mitochondrial membrane potential, nuclear morphology, and defense-related and respiration-related enzyme activities of mycelia were evaluated. The test compound was speculated to obstruct the bio-oxidative process, inhibiting mycelial growth. Compound 6a19 exhibited a satisfactory in vivo control effect on leaf sheath-infected rice plants. After treating rice plants with 50, 100, and 200 μg/mL 6a19, the protective and therapeutic efficacy values were 48.3 and 70.3%, 58.6 and 75.7%, and 69.0 and 81.1%, respectively. Moreover, a linear quantitative structure–activity relationship (R2 = 0.932, F = 61.3, and S2 = 0.020) was established using density functional theory calculations. Four chemical descriptors that were crucial to the antifungal activity were analyzed: the number of occupied electronic levels of atoms, the minimum atomic orbital electronic population, maximum net atom charge for a H atom, and minimum net atomic charge. In overall consideration of experimental results, it was speculated that the target compounds satisfactorily inhibited R. solani by interfering with biological oxidation pathways, which provided an insight into the future intensive and systematic action mechanism. This research is promising for the invention of novel fungicides from natural terpenes with multiple potential targets and satisfactory ecological compatibility.
中文翻译：
含有肟部分的萜烯衍生季环化合物作为潜在杀菌剂的发现
设计并制备了具有肟部分的萜烯衍生季环化合物，以从天然产物中制备杀菌剂。初步评估了其对7种常见病原真菌的抗真菌活性，获得了对立枯丝核菌的半有效浓度（EC 50 ）值。化合物6a 19 （含3-溴噻吩）具有出色的EC 50值（1.62 μg/mL），对形态、超微结构、活性氧产生、线粒体膜电位、核形态和防御相关的影响并评估了菌丝体的呼吸相关酶活性。据推测，测试化合物会阻碍生物氧化过程，抑制菌丝生长。化合物6a 19对叶鞘感染的水稻植物表现出令人满意的体内防治效果。用50、100和200μg/mL 6a 19处理水稻植物后，保护和治疗功效值分别为48.3和70.3%、58.6和75.7%、69.0和81.1%。此外，利用密度泛函理论计算建立了线性定量构效关系（ R 2 = 0.932、 F = 61.3 和S 2 = 0.020）。分析了抗真菌活性至关重要的四个化学描述符：原子占据的电子能级数、最小原子轨道电子布居数、H原子的最大净原子电荷和最小净原子电荷。 综合实验结果，推测目标化合物通过干扰生物氧化途径有效抑制立枯病菌，为未来深入、系统的作用机制提供了思路。该研究有望从天然萜烯中发明具有多个潜在靶点和令人满意的生态相容性的新型杀菌剂。
更新日期：2023-02-07
中文翻译：
含有肟部分的萜烯衍生季环化合物作为潜在杀菌剂的发现
设计并制备了具有肟部分的萜烯衍生季环化合物，以从天然产物中制备杀菌剂。初步评估了其对7种常见病原真菌的抗真菌活性，获得了对立枯丝核菌的半有效浓度（EC 50 ）值。化合物6a 19 （含3-溴噻吩）具有出色的EC 50值（1.62 μg/mL），对形态、超微结构、活性氧产生、线粒体膜电位、核形态和防御相关的影响并评估了菌丝体的呼吸相关酶活性。据推测，测试化合物会阻碍生物氧化过程，抑制菌丝生长。化合物6a 19对叶鞘感染的水稻植物表现出令人满意的体内防治效果。用50、100和200μg/mL 6a 19处理水稻植物后，保护和治疗功效值分别为48.3和70.3%、58.6和75.7%、69.0和81.1%。此外，利用密度泛函理论计算建立了线性定量构效关系（ R 2 = 0.932、 F = 61.3 和S 2 = 0.020）。分析了抗真菌活性至关重要的四个化学描述符：原子占据的电子能级数、最小原子轨道电子布居数、H原子的最大净原子电荷和最小净原子电荷。 综合实验结果，推测目标化合物通过干扰生物氧化途径有效抑制立枯病菌，为未来深入、系统的作用机制提供了思路。该研究有望从天然萜烯中发明具有多个潜在靶点和令人满意的生态相容性的新型杀菌剂。
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