Infection of heart valve through blood stream results in endocarditis that is commonly treated using antibacterial agents. Drug resistance due to extensive use of antibacterial agents motivates the researchers to explore some new antibacterial agents synthetically and naturally from plants sources. This study was intended to compare the antibacterial response of a new eugenol derivative and biosynthesized silver nanoparticle against S. aureus (the endocarditis causing bacteria). The study involved synthesis of new imino derivative of eugenol (IDE) and silver nanoparticles of eugenol rich clove oil. The study involved synthesis of IDE by esterification of eugenol followed by hydrazination and Schiff reaction. The study also involved biosynthesis of silver nanoparticles of clove oil (SNPCO) using AgNO3. The synthesized IDE and biosynthesized SNPCO were characterized using IR, NMR & MASS spectrometry, and UV-vis spectrometry respectively. The synthesized IDE and SNPCO were further evaluated for their antibacterial potential against S. aureus using disk diffusion method. Study revealed high antibacterial potential of IDE when compared to SNPCO. Although the current study reports the new IDE as promising antibacterial agents for infectious endocarditis, however the new IDE must be further evaluated for its preclinical and clinical significance.