Relative stability of formamidine and carbamate groups in the bifunctional pesticide formetanate hydrochloride

Formetanate hydrochloride is a bifunctional pesticide with remarkable solubility, high toxicity, and potential mobility in aqueous environments. The relative stability of the formamidine and carbamate groups in this compound can be used to predict the identity of its degradation products in water. The reported NMR and UV-vis spectroscopic studies revealed that the formamidine group is more labile than the carbamate group under strongly basic conditions, as well as under predetermined field conditions. The half-life of the formamidine group was determined to be 3.9 h under strongly basic conditions (pH 12.6) and 14.4 h under mildly basic conditions (pH 7.6). The longevity of the carbamate group may exceed 6 months due its resistance to base-promoted degradation. These results may be used in the design of more specific remediation technology for formetanate-contaminated surface water.