The synthesis and characterization of composites of oligomeric chitosan with propolis extract which allow the incorporation of a third component (silver nanoparticles) are reported, together with their application in aqueous or hydroalcoholic solutions with a view to the formation of adhesive substances or nanofilms for the protection of vineyards against harmful xylophagous fungi. The antimicrobial properties of the association of the two biological products or those resulting from the incorporation of silver nanoparticles (NPs) are studied and discussed. The efficacy of the chitosan oligomers/propolis/silver NPs ternary system is assessedin vitroforDiplodiafungi. A preliminary study on the convenience of replacing propolis with gentisic acid is also presented.

Phytophthora cinnamomi, responsible for “root rot” or “dieback” plant disease, causes a significant amount of economic and environmental impact. In this work, the fungicide action of nanocomposites based on silver nanoparticles and polyphenol inclusion compounds, which feature enhanced bioavailability and water solubility, was assayed for the control of this soil-borne water mold. Inclusion compounds were prepared by an aqueous two-phase system separation method through extraction, either in an hydroalcoholic solution with chitosan oligomers (COS) or in a choline chloride:urea:glycerol deep eutectic solvent (DES). The new inclusion compounds were synthesized from stevioside and various polyphenols (gallic acid, silymarin, ferulic acid and curcumin), in a [6:1] ratio in the COS medium and in a [3:1] ratio in the DES medium, respectively. Their in vitro response against Phytophthora cinnamomi isolate MYC43 (at concentrations of 125, 250 and 500 µg·mL−1) was tested, which found a significant mycelial growth inhibition, particularly high for the composites prepared using DES. Therefore, these nanocomposites hold promise as an alternative to fosetyl-Al and metalaxyl conventional systemic fungicides.

Fusarium culmorum is a soil-borne fungus able to cause Fusarium head blight, one of the most important cereal diseases worldwide, which can result in significant yield losses of up to 50% and which jeopardizes food and feed safety due to the mycotoxins produced. In the study presented herein, the enhancement of the antifungal activity against this pathogen, resulting from the addition of silver nanoparticles (AgNPs) to different polyphenol-stevioside inclusion compounds, dispersed either in a chitosan oligomers hydroalcoholic solution or in a choline chloride:urea:glycerol deep eutectic solvent, was investigated in vitro. The polyphenols assayed were curcumin, ferulic acid, gallic acid and silymarin. Four composite concentrations (62.5, 125, 250 and 500 µg·mL−1), with and without AgNPs, were assessed, finding noticeable differences in mycelial growth inhibition, with EC50 and EC90 values ranging from 118 to 579 µg·mL−1 and from 333 to 2604 µg·mL−1, respectively. The obtained results evidenced the improved efficacy of the composites with AgNPs, a superior performance of the composites based on curcumin and ferulic acid, and the advantages of the deep eutectic solvent-based dispersion medium over the chitosan oligomers-based one. The reported composites hold promise for crop protection applications.

Broad scale use of chemical pesticides is known to have produced broad scale environmental impact worldwide and, at the same time, discovery and registration of new molecules to be used as insecticides, herbicides and fungicides have slowed significantly along the last decades, reducing the number of options for pest control by the farmers. Searches for novel environmentally friendly products are a recognized priority. In this work, aqueous solutions of chitosan oligomers (COs) and propolis (P), individually or as binary mixtures, were tested against Hemileia vastatrix, the fungus which causes coffee leaf rust, the worst disease of coffee. Germination of H. vastatrix was inhibited up toll 99 % by COs, followed by the mixture of COs-P and P individually (germination inhibition of 96 % and 54 % respectively). Testing those products on detached coffee leaf discs also produced promising results when COs were applied before H. vastatrix inoculation. These results may lead to the discovery of new antifungal products for the control of coffee leaf rust.

Phytophthora cinnamomi is responsible for radical rot in a wide range of hosts, resulting in large economic and ecological losses worldwide. In Spain, it is responsible for diseases such as the oak decline or the chestnut blight. In this study, different polyphenol-stevioside inclusion compounds dispersed in a hydroalcoholic solution of chitosan oligomers have been investigated, with a view to their application as natural bioactive complexes to replace conventional systemic fungicides against this fungus. The polyphenols tested in vitro were curcumin, ferulic acid, gallic acid and silymarin. Three concentrations (125, 250 and 500 µg·mL −1 ) were assayed, with and without silver nanoparticles (AgNPs), and notable differences were found in the inhibition of mycelium growth, with EC 50 and EC 90 values ranging from 171 to 373.6 µg·mL −1 , and from 446.2 to 963.7 µg·mL −1 , respectively. The results obtained showed that the addition of AgNPs, despite their antimicrobial activity, did not always lead to synergies. In the case of P. cinnamomi, an unexpected antagonistic behavior was found for two of the polyphenols (curcumin and silymarin), while an additive behavior for ferulic acid and a synergistic behavior for gallic acid were attained. In view of their inhibitory power, the preparations based on ferulic acid with AgNPs and on silymarin without AgNPs are proposed for applications in crop and forests protection against P. cinnamomi.

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