Fungicidal Activity and Mechanism of Action of Glabridin from Glycyrrhiza glabra L.

Glycyrrhiza glabra (Licorice) belongs to the Fabaceae family and its extracts have exhibited significant fungicidal activity against phytopathogenic fungi, which has mainly been attributed to the presence of phenolic compounds such as flavonoids, isoflavonoids and chalcones. In this study, a series of licorice flavonoids, isoflavonoids and chalcones were evaluated for their fungicidal activity against phytopathogenic fungi. Among them, glabridin exhibited significant fungicidal activity against ten kinds of phytopathogenic fungi. Notably, glabridin displayed the most active against Sclerotinia sclerotiorum with an EC50 value of 6.78 µg/mL and was 8-fold more potent than azoxystrobin (EC50, 57.39 µg/mL). Moreover, the in vivo bioassay also demonstrated that glabridin could effectively control S. sclerotiorum. The mechanism studies revealed that glabridin could induce reactive oxygen species accumulation, the loss of mitochondrial membrane potential and cell membrane destruction through effecting the expression levels of phosphatidylserine decarboxylase that exerted its fungicidal activity. These findings indicated that glabridin exhibited pronounced fungicidal activities against S. sclerotiorum and could be served as a potential fungicidal candidate.

Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight

The increasing resistance of rice sheath blight caused by Rhizoctonia solani highlights the need for highly effective and environmentally benign agents. Natural β-carboline alkaloids were simplified to obtain a series of indole derivatives, and their fungicidal activity and preliminary mode of action against R. solani were also evaluated. The initial hit indole (7) displayed significant fungicidal activity with an EC50 value of 25.56 μg/mL, and was selected for further optimization. Importantly, compound 55, the most active compound, had an EC50 value of 0.62 μg/mL, and approximately 300-fold more potent than validamycin A (EC50 = 183.00 μg/mL). In vivo bioassay also demonstrated that compound 55 showed better fungicidal activities than validamycin A. Moreover, the mechanism studies revealed that compound 55 not only caused remarkable morphological and structural alterations of R. solani hyphae, but also induced the loss of mitochondrial membrane potential and interfered with DNA synthesis. Therefore, compound 55 showed superior fungicidal activity against R. solani, and the elucidated mode of action supported the potential application of compound 55 against rice sheath blight.

Synthesis and Fungicidal Activity of (E)-5-[1-(4-Phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one Derivatives

(E)-5-[1-(4-Phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)eth­yl­idene]-2-aminoimidazolin-4-one derivatives, as novel fungicidal agents, are designed and synthesized in moderate to excellent yields in four steps from (1-hydroxycyclohexyl)(phenyl)methanone and diketene as the starting materials. The products are characterized by 1H NMR and HRMS (ESI) analysis. An in vivo bioassay shows that some of the products exhibit good to excellent inhibition against P. cubensis and C. lagenarium, whilst up to 94.7% inhibition against P. capsici and up to 78.1% inhibition against B. cinerea is demonstrated in the in vitro bioassay. EC50 values of 3.40 and 5.86 μg/mL are demonstrated against P. capsici and B. cinerea.

Contribution of Mid-Season Cover Sprays to Management of Peach Brown Rot at Harvest

Four protectant fungicides applied as midseason cover sprays were quantitatively assessed for their ability to reduce brown rot caused by Monilinia fructicola during the preharvest fruit ripening periods in the 2012 through 2015 growing seasons. No fungicides were applied during bloom or during the preharvest period. Treatment programs consisted of captan, sulfur, ziram, and thiram applications beginning at early shuck-split stage and ending with the final cover spray at 23 to 26 days before harvest. The incidence of brown rot at harvest was determined by examining 41 to 91 fruit for symptoms of rot on each of four replicate trees for each treatment. The incidence of sporulating blossom blight cankers was assessed during the preharvest period at 8, 15, and 22 days after the final cover spray. An in vivo bioassay was also conducted at 7, 14, and 21 days after the final cover spray to ascertain the level of fungicide residue during the preharvest period. The bioassay uses conidia germination as a quantitative indicator of effective residue. Results of the harvest assessment showed that captan cover sprays significantly reduced brown rot incidence in all years of the study. Furthermore, results of the bioassay demonstrated that fungicide residue was the mechanism by which this control occurred. None of the other fungicide cover spray programs contributed significantly to brown rot control at harvest in any year, and bioassay results showed insufficient residue to inhibit conidial germination. Antisporulant activity against blossom blight cankers was not observed for any fungicide program, indicating that reducing inoculum production from this source was not a mechanism for brown rot control. The captan and sulfur programs provided very good control of peach scab incidence and severity, caused by Fusicladium carpophilum, while the ziram and thiram programs failed to control this disease. These findings demonstrated that captan cover sprays can contribute significantly to control of brown rot at harvest, thereby augmenting the efficacy and consistency of management by preharvest fungicide programs. Furthermore, any reduction of the M. fructicola population by the captan cover sprays should reduce selection pressure against the site-specific fungicides commonly used during the preharvest period, thereby prolonging their useful life for brown rot control.