Chemical Reduction of Zoalene to ANOT for Use in Zoalene Residue Studies

Abstract

A novel chemical synthesis and purification scheme to produce ANOT (3-amino-5-nitro-o-toluamide) was developed to yield an analytical standard grade material for zoalene residue investigations. An original conversion of zoalene (3,5-dinitro-o-toluamide) to ANOT was developed. Several literature references were available for the partial reduction of dinitro aryl compounds, but none detailed the conversion of zoalene to ANOT. A chemical synthesis was chosen over a biological synthesis due to the latter's complex reaction matrix, difficult recovery, and low batch yields. Using general partial reduction of dinitro aryl schemes, it was found that 10% palladium on carbon coupled to a cyclohexene reducing agent provided an optimum ANOT yield. Chromatographic techniques were utilized to isolate ANOT from the product mixture and to purify it to a standard grade material (>99% pure). The chemically synthesized ANOT product was characterized using colorimetric, TLC, FTIR, NMR, and LC/MS techniques. Keywords: ANOT; zoalene; zoaline residue; chemical reduction

Pesticides

“…Chlorpyrifos and its by-products were detected with various reagents, and the technique was compared to fluorescence quenching detection (183). The plate was then sprayed with a Bratton-Marshal solution (0.4% naphthylethylenediamine dihydrochloride solution in methanol) (187). Visual comparison was made against a standard equivalent to the maximum residue level (MRL) set by European countries (184).…”

Simultaneous Determination of Zoalene and Its Metabolite in Chicken Muscle and Liver by SPE and UPLC–MS-MS

“…To determine zoalene and its metabolite in biological samples, only few methods using thin layer chromatography [3], spectrophotometry [4,5], and LC [6][7][8][9] have been developed. Moreover, most of these methods cannot be used for the simultaneous determination of zoalene and 3-ANOT.…”