Synthesis and biological activities of (e)-3-(substituted phenyl)-n-(pyridin-2-yl) acrylamides and substituted benzamides
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Date
2022-01, 2022-01
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G. B. Pant University of Agriculture and Technology, Pantnagar
G. B. Pant University of Agriculture and Technology, Pantnagar
G. B. Pant University of Agriculture and Technology, Pantnagar
Abstract
Green chemistry techniques were used to prepare (E)-3-(substituted phenyl)-N( pyridin-2-yl) acrylamides utilising triethylamine, 2-aminopyridine and substituted cinnamic acids, which were synthesized via Doebner modification of substituted benzaldehydes with pulverized malonic acid along with few drops of piperidine and pyridine. Benzamides were synthesized via Beckmann rearrangement utilising substituted ketone, hydroxylamine hydrochloride CaCl2.2H2O and Formic acid. IR and NMR spectrum analysis were used to confirm the structures of sample compounds. Antioxidant and herbicidal activities were also studied on the produced compounds. Seed germination inhibition activity of compounds was evaluated against Raphanus sativus seeds at different concentrations. In (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides the majority of the compounds were found to be active. At 300 ppm concentration, maximum seed germination inhibition activity was exhibited by the compound A-6 at 83.3 % inhibition, followed by the compounds A-4 and M-3 at 79.2 and 70.8 % inhibition respectively. In case of benzamides, at 300 ppm concentration maximum seed germination inhibition activity was exhibited by the compound K-4 at 82.5 %. At all doses, all the synthesized compounds had lower activity than the reference pendimethalin. The DPPH antioxidant activity of all compounds was asseyed. The (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides, compound A-7 exhibited maximum DPPH radical scavenging activity followed by A-10. In case of benzamides, K-6 compound exhibited the maximum DPPH radical scavenging activity. All the synthesized compounds exhibit lower radical scavenging activity than both the standard gallic acid and BHT. Hydrogen peroxide (H2O2) radical scavenging activity for synthesized compounds was also studied. The compound A-7 showed highest radical scavenging activity amongst all the s d n u o p m o c d n a s d n u o p m o c d e z i s e h t n y s A- 1 . y t i v i t c a t s e w o l d e w o h s , s e d i m a z n e b n I K- 6 showed highest free radical scavenging activity amonest all the synthesized compounds. Radical scavenging activity of all the synthesized compounds were compared against the standard BHT. The current study suggests that (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides and Benzamide derivatives might be used as potential herbicides and antioxidants to protect agricultural crops, foods, and other products (E)-3-(substituted phenyl)-N-(pyridin- 2-yl) acrylamides and Benzamide derivatives compounds have good to moderate antioxidant and herbicidal action, and might be used as antioxidants and herbicides in the future.
Green chemistry techniques were used to prepare (E)-3-(substituted phenyl)-N( pyridin-2-yl) acrylamides utilising triethylamine, 2-aminopyridine and substituted cinnamic acids, which were synthesized via Doebner modification of substituted benzaldehydes with pulverized malonic acid along with few drops of piperidine and pyridine. Benzamides were synthesized via Beckmann rearrangement utilising substituted ketone, hydroxylamine hydrochloride CaCl2.2H2O and Formic acid. IR and NMR spectrum analysis were used to confirm the structures of sample compounds. Antioxidant and herbicidal activities were also studied on the produced compounds. Seed germination inhibition activity of compounds was evaluated against Raphanus sativus seeds at different concentrations. In (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides the majority of the compounds were found to be active. At 300 ppm concentration, maximum seed germination inhibition activity was exhibited by the compound A-6 at 83.3 % inhibition, followed by the compounds A-4 and M-3 at 79.2 and 70.8 % inhibition respectively. In case of benzamides, at 300 ppm concentration maximum seed germination inhibition activity was exhibited by the compound K-4 at 82.5 %. At all doses, all the synthesized compounds had lower activity than the reference pendimethalin. The DPPH antioxidant activity of all compounds was asseyed. The (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides, compound A-7 exhibited maximum DPPH radical scavenging activity followed by A-10. In case of benzamides, K-6 compound exhibited the maximum DPPH radical scavenging activity. All the synthesized compounds exhibit lower radical scavenging activity than both the standard gallic acid and BHT. Hydrogen peroxide (H2O2) radical scavenging activity for synthesized compounds was also studied. The compound A-7 showed highest radical scavenging activity amongst all the s d n u o p m o c d n a s d n u o p m o c d e z i s e h t n y s A- 1 . y t i v i t c a t s e w o l d e w o h s , s e d i m a z n e b n I K- 6 showed highest free radical scavenging activity amonest all the synthesized compounds. Radical scavenging activity of all the synthesized compounds were compared against the standard BHT. The current study suggests that (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides and Benzamide derivatives might be used as potential herbicides and antioxidants to protect agricultural crops, foods, and other products (E)-3-(substituted phenyl)-N-(pyridin- 2-yl) acrylamides and Benzamide derivatives compounds have good to moderate antioxidant and herbicidal action, and might be used as antioxidants and herbicides in the future.
Green chemistry techniques were used to prepare (E)-3-(substituted phenyl)-N( pyridin-2-yl) acrylamides utilising triethylamine, 2-aminopyridine and substituted cinnamic acids, which were synthesized via Doebner modification of substituted benzaldehydes with pulverized malonic acid along with few drops of piperidine and pyridine. Benzamides were synthesized via Beckmann rearrangement utilising substituted ketone, hydroxylamine hydrochloride CaCl2.2H2O and Formic acid. IR and NMR spectrum analysis were used to confirm the structures of sample compounds. Antioxidant and herbicidal activities were also studied on the produced compounds. Seed germination inhibition activity of compounds was evaluated against Raphanus sativus seeds at different concentrations. In (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides the majority of the compounds were found to be active. At 300 ppm concentration, maximum seed germination inhibition activity was exhibited by the compound A-6 at 83.3 % inhibition, followed by the compounds A-4 and M-3 at 79.2 and 70.8 % inhibition respectively. In case of benzamides, at 300 ppm concentration maximum seed germination inhibition activity was exhibited by the compound K-4 at 82.5 %. At all doses, all the synthesized compounds had lower activity than the reference pendimethalin. The DPPH antioxidant activity of all compounds was asseyed. The (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides, compound A-7 exhibited maximum DPPH radical scavenging activity followed by A-10. In case of benzamides, K-6 compound exhibited the maximum DPPH radical scavenging activity. All the synthesized compounds exhibit lower radical scavenging activity than both the standard gallic acid and BHT. Hydrogen peroxide (H2O2) radical scavenging activity for synthesized compounds was also studied. The compound A-7 showed highest radical scavenging activity amongst all the s d n u o p m o c d n a s d n u o p m o c d e z i s e h t n y s A- 1 . y t i v i t c a t s e w o l d e w o h s , s e d i m a z n e b n I K- 6 showed highest free radical scavenging activity amonest all the synthesized compounds. Radical scavenging activity of all the synthesized compounds were compared against the standard BHT. The current study suggests that (E)-3-(substituted phenyl)-N-(pyridin-2-yl) acrylamides and Benzamide derivatives might be used as potential herbicides and antioxidants to protect agricultural crops, foods, and other products (E)-3-(substituted phenyl)-N-(pyridin- 2-yl) acrylamides and Benzamide derivatives compounds have good to moderate antioxidant and herbicidal action, and might be used as antioxidants and herbicides in the future.