Synthesis of N-substituted-3(4-hydroxy-3-methoxy phenyl) acrylamide derivatives and their fungitoxicity
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Date
2019
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Punjab Agricultural University, Ludhiana
Abstract
Ferulic acid is an abundant phenolic phytochemical component, possessing many medicinal properties. Derivatives of ferulic acid, show stronger physiological activities and are less toxic than ferulic acid. The amide moiety is one of the most significant chemical building block found in nature. An efficient synthetic pathway for synthesizing derivatives of N-substituted-3(4-hydroxy-3-methoxyphenyl) acrylamide was evolved in the present study, and eight compounds (I-VIII) were synthesized in appreciable yields. The synthetic route involved acetylation of hydroxyl group of ferulic acid followed by amidation with 4-aminobenzoic acid. The resultant compound hence formed, 4-(3-(4-acetoxy-3-methoxyphenyl)acrylamido)benzoic acid (II), was then condensed with different heterocyclic amines, viz., 4-aminophenazone, substituted amino-pyridines and substituted amino-1,2,4-triazoles, in the presence of base (triethylamine), to obtain amides (III-VIII), which were identified and characterized on the basis of physical data and spectroscopic studies (UV, IR and 1H NMR), respectively. All the synthesized compounds along with ferulic acid were screened in vitro for their fungitoxicity against three phytopathogenic fungi of maize, viz Rhizoctonia solani, Macrophomina phaseolina and Fusarium moniliforme using poisoned food technique. Comprehensive perusal of the results proclaimed that introduction of 3-amino-1,2,4-triazole moiety in the acetyl ferulic acid and 4-aminobenzoic acid-containing structure (compound VIII) increased their fungitoxic effect against mycelial extension of R. solani (ED50 = 38 μg ml-1), as well as F. moniliforme (ED50 = 840 μg ml-1). However, the degree of inhibition of compound (VIII) was lesser in the event of F. moniliforme than that of R. solani. On the contrary, incorporation of 4-aminobenzoic acid moiety in acetyl ferulic acid (compound II), elevated its fungitoxicity in case of M. phaseolina (ED50 = 86 μg ml-1). Moreover, no synthesized compound was more potent than the Carbendazim 50WP standard against all the three tested fungi.
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