Infection of meningeal layer due to Streptococcus pneumoniae results in meningitis that can be treated by antibacterial agents. Resistance development on continuous exposure to antibacterial agents, alarms investigators to find some new antibacterial agents both synthetically and naturally via plants sources. Current investigation was intended to compare the antibacterial response of new menthol analogues and biosynthesized silver nanoparticles against S. pneumoniae (the meningitis causing bacteria). The study involved synthesis of new imino analogues of menthol (IAM) and silver nanoparticles of menthol rich mentha oil. Current investigation involved synthesis of IAM by esterification of menthol followed by hydrazination and Schiff’s reaction. This study also involved biosynthesis of silver nanoparticles of mentha oil (SNPMO) using AgNO3. The synthesized IAM and biosynthesized SNPMO were characterized using IR, NMR & MASS spectrometry, and UV-Vis. Spectrometry respectively. The synthesized IAM and SNPMO were further evaluated for their antibacterial potential against S. pneumoniae using disk diffusion method. Study revealed high antibacterial potential of IAM when compared to SNPMO. Although, current study reports the new IAM as promising antibacterial agents for infectious meningitis, however, the new IAM should be further evaluated for its preclinical and clinical significance.