The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens

Abstract

Terbinafine, an inhibitor of squalene epoxidase in ergosterol biosynthesis, is chiefly utilized as an antifungal medication with potential uses in pesticide applications. This study explores the fungicidal efficacy of terbinafine against prevalent plant pathogens and confirms its effectiveness. To augment its water solubility, five ionic salts of terbinafine were synthesized by pairing them with organic acids. Among these salts, TIS 5 delivered the most impressive results, amplifying the water solubility of terbinafine by three orders of magnitude and lessening its surface tension to facilitate better dispersion during spraying. The in vivo experiments on cherry tomatoes showed that TIS 5 had a superior therapeutic activity compared to its parent compound and two commonly used broad−spectrum fungicides, pyraclostrobin and carbendazim. The results highlight the potential of terbinafine and its ionic salts, particularly TIS 5, for use as fungicides in agriculture due to their synergistic effects with furan−2−carboxylate.

Quality assurance of postharvest grapes against Botrytis cinerea by terbinafine

“…Compared with boscalid, terbinafine completely restrained the occurrence of gray mold decay at 400 mg·L −1 , which showed direct evidence that terbinafine has the potential to be used to control B. cinerea during the storage period. Previous research synthesized five terbinafine ionic salts, and those compounds could effectively reduce infection diameters by B. cinerea on the cherry tomatoes at 20 mg/L [ 20 ].…”

Ion exchanger‐based electrodes for determination of highly lipophilic physiologically active amines: Peculiarities of functioning and ways for improving analytical characteristics

“…In particular, according to [24], changing pH values from 4 to 9 does not affect the potential of terbinafine-SE in 1×10 À 3 M solution of terbinafine hydrochloride, while according to [25] the potential values in a 1×10 À 4 M solution remain unchanged in the pH range 7-9. It should be noted that the operating pH ranges given in [24,25] do not agree with the data on the solubility of the molecular form of terbinafine in water, which is 5.22 μM [27]. The pKa values of terbinafine given in the literature are characterized by a large scatter (from 7.05 to 8.94) [27][28][29], however, even with the maximum of the given values, the solubility of terbinafine at pH = 9 should not exceed 5×10 À 6 M. Further, according to [15] and [29], the potential of terbinafine-SE remains constant in the pH ranges 3-6 and 1-3, respectively, after which a sharp decrease in the potential occurs.…”

“…It should be noted that the operating pH ranges given in [24,25] do not agree with the data on the solubility of the molecular form of terbinafine in water, which is 5.22 μM [27]. The pKa values of terbinafine given in the literature are characterized by a large scatter (from 7.05 to 8.94) [27][28][29], however, even with the maximum of the given values, the solubility of terbinafine at pH = 9 should not exceed 5×10 À 6 M. Further, according to [15] and [29], the potential of terbinafine-SE remains constant in the pH ranges 3-6 and 1-3, respectively, after which a sharp decrease in the potential occurs. The data presented in [29] are consistent with those obtained by us and seem to be the most reliable, although the given explanation of the drop in potential due to a decrease in the solubility of terbinafine at pH > 3, is not consistent with the rather high basicity of terbinafine.…”

A Novel Potentiometric Coated Wire Sensor Based on Functionalized Polymeric CaO/ZnO Nanocomposite Synthesized by Lavandula Spica Mediated Extract for Terbinafine Determination

“…Similar to other allylamines, it blocks the enzyme squalene epoxidase, which jeopardizes ergosterol synthesis in the cell membrane and leads to an intracellular accumulation of squalene, resulting in lysis of the fungal cells. [1,2] Chemically, terbinafine is primarily present as terbinafine hydrochloride, which is readily soluble in methanol and methylene chloride, in ethanol and slightly soluble in water. It is a highly lipophilic molecule that tends to accumulate in the skin, nails and fatty tissue.…”