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)..
