Date of Graduation

12-2018

Document Type

Thesis

Degree Name

Master of Science in Chemistry (MS)

Degree Level

Graduate

Department

Chemistry & Biochemistry

Advisor/Mentor

McIntosh, Matthias C.

Committee Member

Thallapuranam, Suresh

Second Committee Member

Willett, Cammy D.

Third Committee Member

Beyzavi, M. Hassan

Keywords

Dicamba; Organic Synthesis

Abstract

The most popular herbicide used for weed control has been glyphosate for many years in the Midwestern United States. Plants have begun to develop a resistance to glyphosate due to over use of the herbicide. This herbicide resistance has pushed farmers to turn to alternative herbicides such as dicamba and 2,4-D. Recently agrochemical companies have developed genetically modified crops that are resistant to herbicides such as dicamba. These modified crops allow farmers to spray their fields with dicamba without fear of crop damage. Farmers of non-genetically modified crops, however, suffer damage and loss of yield from herbicide drift effects of this spraying. We sought to prepare the dicamba glucosides, DCSA-glucoside, DCGA-glucoside, and 5-OH dicamba-glucoside standards for LC/MS/MS analysis. Pure samples of these glucosides will provide a reference point in which to study how genetically modified plants metabolize dicamba. Efforts to prepare these glucoside samples, will be discussed. Experiments done for the glucoside synthesis followed a Michael glycosylation type reaction using a glucosyl halide, aromatic phenolic compound, in the presence of a biphasic catalyst, tetrabutylammonium bromide. Reactions failed to yield desired products or were unable to be purified. Further investigation into other types of glycosylation reactions is necessary to continue synthesis of the desired glucosides.

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