Degradation of isoxaflutole (balance) herbicide by hypochlorite in tap water.

Chlorine has been widely employed for the disinfection of drinking water. Additionally, it has the capacity to oxidize many organic compounds in water. Isoxaflutole (Balance; IXF) belongs to a new class of isoxazole herbicides. Isoxaflutole has a very short soil half-life and rapidly degrades to a stable and phytotoxic metabolite, diketonitrile (DKN). Further degradation of DKN produces a nonbiologically active benzoic acid (BA) metabolite. In experiments using high-performance liquid chromatography-UV spectroscopy (HPLC-UV) and HPLC tandem mass spectrometry (HPLC-MS/MS), DKN was found to rapidly react with hypochlorite in tap water, yielding the BA metabolite as the major end product. One milligram per liter (19 microM) of hypochlorite residue in tap water was able to completely oxidize up to 1600 microg/L (4.45 micromol/L) of DKN. In tap water, the disappearance of IXF was much more rapid than in DI water. As soon as the IXF is hydrolyzed to DKN, the DKN quickly reacts with the OCl(-) to form nonphytotoxic BA. As a result, the herbicide solutions prepared with tap water at 500 microg/L will no longer possess any herbicidal activity after 48 h of storage. However, in agronomic settings, highly concentrated tank solutions (600-800 mg/L) may be prepared with tap water since the conversion of IXF to BA would represent <5% of the herbicide; therefore, any impact on the herbicide efficacy would be negligible. Results of this study show that current chlorination disinfection protocols in municipal water systems would completely eliminate the phytotoxic form of this new herbicide, DKN, from drinking water supplies; yet, farmers can use chlorinated tap water without significant loss of efficacy.

Determination of isoxaflutole (balance) and its metabolites in water using solid phase extraction followed by high-performance liquid chromatography with ultraviolet or mass spectrometry.

Balance (isoxaflutole, IXF) belongs to a new family of herbicides referred to as isoxazoles. IXF has a very short soil half-life (<24 h), degrading to a biologically active diketonitrile (DKN) metabolite that is more polar and considerably more stable. Further degradation of the DKN metabolite produces a nonbiologically active benzoic acid (BA) metabolite. Analytical methods using solid phase extraction followed by high-performance liquid chromatography-UV (HPLC-UV) or high-performance liquid chromatography-mass spectrometry (HPLC-MS) were developed for the analysis of IXF and its metabolites in distilled deionized water and ground water samples. To successfully detect and quantify the BA metabolite by HPLC-UV from ground water samples, a sequential elution scheme was necessary. Using HPLC-UV, the mean recoveries from sequential elution of the parent and its two metabolites from fortified ground water samples ranged from 68.6 to 101.4%. For HPLC-MS, solid phase extraction of ground water samples was performed using a polystyrene divinylbenzene polymer resin. The mean HPLC-MS recoveries of the three compounds from ground water samples spiked at 0.05-2 microg/L ranged from 100.9 to 110.3%. The limits of quantitation for HPLC-UV are approximately 150 ng/L for IXF, 100 ng/L for DKN, and 250 ng/L for BA. The limit of quantitation by HPLC-MS is 50 ng/L for each compound. The methods developed in this work can be applied to determine the transport and fate of Balance in the environment.