The search for more active antimicrobial agents is a persistent process. Moreover, increasing prevalence of resistant miroorganisms to common antimicrobial agents necessitates the search for new active compounds. To this end, we prepared a series of novel compounds containing both cis-gem-dichlorocyclopropane and aromatic carbamate moieties-some with mono and dichloro substitution 9a-f. For comparison purposes known and new compounds containing four carbon spacers, both alkane 7a-f and cis alkene 8a-f dicarbamate analogues were also prepared. All compounds were characterized by NMR, FTIR and HR-MS Spectrometry. The prepared compounds were screened against representative gram negative bacteria, yeast and gram positive bacteria. Excellent trends for antimicrobial activity were observed mainly against gram positive bacteria. The cis-gem-dichlorocyclopropane spacer targets (Series 9) exhibited the strongest activity with three out of the six compounds from series 9 having activity against (S. aureus 29213) that are stronger than that of commercial antibiotics tested. The excellent activity of the new system 9 against gram positive strains can provide a future promise in the search for new antimicrobial agent.