Pine Rosin as a Valuable Natural Resource in the Synthesis of Fungicide Candidates for Controlling Fusarium oxysporum on Cucumber

Abstract

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 in vitro antifungal activity against Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium oxysporum, and Magnaporthe oryzae, rosin-based 1,3,4-thiadiazole compounds containing thiophene heterocycles were screened. Notably, compound 3e [dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide] exhibited excellent antifungal property against F. oxysporum with an EC50 of 0.618 mg/L, which was lower than that of the positive control carbendazim (0.649 mg/L). The in vivo antifungal activity results showed that 3e exerted a protective effect on cucumber plants. Physiological and biochemical studies showed that the primary mechanism of action of compound 3e on F. oxysporum 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 3e 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.

Synthesis, Antifungal Activity, Cytotoxicity and QSAR Study of Camphor Derivatives

“…The in vitro antifungal activity of the camphor derivatives against six fungi was evaluated using the mycelium growth rate method [ 27 ], with the commercial fungicides tricyclazole and carbendazim serving as positive controls. Dimethyl sulfoxide was used as a carrier control.…”

Discovery of Natural Rosin Derivatives Containing Oxime Ester Moieties as Potential Antifungal Agents to Control Tomato Gray Mold Caused by Botrytis cinerea

“…To improve the physical and chemical properties of rosin or strengthen its pharmacological action, thereby enhancing its biological activity, its molecular structure usually must be modified. 7 Oxime esters are a paramount class of nitrogen-containing compounds that are often used as high-efficiency intermediates for the synthesis of medicine and pesticides. Oxime ester compounds have a wide range of biological activities as pesticides and advantages including low residues and low toxicity.…”

Experimental Determination and Computational Prediction of Dehydroabietic Acid Solubility in (−)-α-Pinene + (−)-β-Caryophyllene + P-Cymene System

“…Pine resin is an inexpensive and biodegradable natural resource, which is abundant in pine and coniferous trees [1]. It is commonly used as an antimicrobial agent [2], paint, ink toner, and for coatings [3,4]. The most important products of pine resin are rosin and turpentine obtained via distillation [5].…”