SYNTHESIS, CHARACTERIZATION AND BIOACTIVITY STUDIES OF 2,5-DIMETHYL-4-NITROANISOLE AND 2,5-DIMETHYL-4-METHOXY ANILINOACETIC ACID.

Abstract

The need for the development of new compounds to combat weed resistance to herbicides and microbial resistance to drugs has led to this research. The research aimed at synthesizing 2,5-dimethyl-4-methoxy anilinoacetic acid and 3,6-dimethyl-4-methoxy aniline acetic acid and studying their biological and herbicidal activites. 10g of p-xylenol was o-methylated using dimethyl sulphate in a basic medium (sodium hydroxide) was carried out on p-Xylenol to give 2,5-dimethyl 4-methoxy anisole. Nitration was carried out on the anisole compound using acetic acid in nitric acid. Reduction reaction was carried out on the Nitro compound using tin metal in hydrochloric acid to give 2,5-dimethyl-4-methoxy aniline. The aniline compound was treated with chloroacetic acid in pyridine to afford 2,5-dimethyl-4-methoxy anlinoacetic acid and 3,6-dimethyl-2-methoxy anilinoacetic acid as a colorless solid . Fourier Transform Infra-Red Spectrometer (FTIR), Proton Nuclear Magnetic Resonance(1H NMR) and Carbon 13 Nuclear magnetic Resonance (13C NMR) were run to ascertain the structures.2,5-dimethyl nitroanisole(compound A) and 2,5-dimethyl-4-methoxy anilinoacetic acid (Compound B) were screened for antimicrobial activities at 10mg/L. The results obtained from antibacterial screening showed that the compounds possessed some antibacterial activity against the test bacteria (Staphycoccus aureus, Enterobacteraerogenes, Streptococcus bovis, Erwinnicarotorora, Xanthomonasaxomopidis and pseudomonas aeroginosa), even though the standard (streptomycin) was more potent against the test bacteria than the two of them with the exception of Erwinnicarotorora, a gram-negative bacteria in which 2,5-dimethyl nitroanisole performed better. The activity of the 2,5-dimethyl nitroanisole was higher than 2,5-dimethyl-4-methoxy anilinoaceticagainst all test organisms except pseudomonas aeroginosa. Furthermore, the synthesized compounds exhibited antifungal property against plant pathogenic fungi namely; Sclerotiumrolfsin, Pthopthimpalmivora and Cercosponioryzoned even though the standard (Kocide) exhibited stronger activity than the two compounds.Herbicidal bioassay was carried out on the two compounds against the test weeds; monocotyledous (Eleusinaindica and Panicum maximum) and dicotyledous (Chromolaenaodorata and Ageratum conyzoides) for five weeks, using 2,4-D as standard. The results obtained showed that the two compounds exhibited no herbicidal property at the concentration applied (0.15%v/v and 0.30%v/v)..