Synthesis and biological activities of Cinnamo Hydroxamic acid derivatives
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Date
2019-06
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G.B. Pant University of Agriculture and Technology, Pantnagar - 263145 (Uttarakhand)
Abstract
The cinnamo hydroxamic acid derivatives have been synthesized employing green chemistry principles. The compounds have been synthesized by the reaction of substituted cinnamic acids and substituted hydroxylamines at temperature 0°C in chloroform as solvent and solution was in the presence of a new catalyst triethylamine . The compounds synthesized are 4-hydroxy cinnamo hydroxamic acid, 3-nitro cinnamo hydroxamic acid, 4-methoxy cinnamo hydroxamic acid, 4-chloro cinnamo hydroxamic acid, o-tolyl-(4-hydroxyl) cinnamon hydroxamic acid, o-tolyl-(3-nitro) cinnamo hydroxamic acid, o-tolyl-(3-bromo) cinnamon hydroxamic acid, o-tolyl-(4-methoxy) cinnamo hydroxamic acid, o-tolyl-(3-chloro) cinnamon hydroxamic acid and 2-Bromo-(4-chloro) cinnamo hydroxamic acid. All the compounds were formed with average to good yield. The compounds were tested for herbicidal activity against Raphanus sativus seeds. The compound 3-nitro cinnamon hydroxamic acid, o-tolyl-(3-bromo) cinnamo hydroxamic acid and 2-Bromo-(4-chloro) cinnamo hydroxamic acid were found to exhibit significant activity at par with the standard pendimethalin at concentration 200ppm. Other compounds exhibited activity significantly lower than the standard at all concentrations. Antioxidant activity of the synthesized compounds was also evaluated for antioxidant activity two methods viz., 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and reducing antioxidant power (FRAP) were employed. Most of the compounds were found to have significant activity. Amongst all the substituted cinnamo hydroxamic acid derivatives 4-hydroxy cinnamo hydroxamic acid exhibited the highest radical scavenging activity followed by 4-chloro cinnamo hydroxamic acid, o-tolyl-(3-bromo) cinnamo hydroxamic acid, 3-nitro cinnamo hydroxamic acid, o-tolyl-(4-methoxy) cinnamo hydroxamic acid, o-tolyl-(4-hydroxyl) cinnamo hydroxamic acid, 4-methoxy cinnamo hydroxamic acid exhibiting activity at par with standard BHT / gallic acid.The compounds o-tolyl-(3-chloro) cinnamo hydroxamic acid, 2-Bromo-(4-chloro) cinnamo hydroxamic acid exhibited lower activity than standard BHT and higher activity than standard gallic acid while compound o-tolyl-(3-nitro) cinnamo hydroxamic acid exhibit lowest radical scavenging activity than both standard BHT and gallic acid. The reducing power activity (FRAP) of synthesized compounds were also studied. The highest reducing power activity was observed for o -tolyl-(4-methoxy) cinnamo hydroxamic acid while, the lowest activity was observed in 4-hydroxy cinnamo hydroxamic acid .The reducing power activities for all the synthesized compounds were compared with standard FeSO4.7H2O. It may be concluded from the present study that cinnamo hydroxamic acid derivatives might be a source of herbicides and antioxidants to protect the agricultural crops, foods etc. Cinnamo hydroxamic acid derivatives show excellent herdicidal and antioxidant activity and may be developed as potential herbicides and antioxidants in future.
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