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Kansas Water Science Center

Deisopropylatrazine in Groundwater as an Indicator of Past Cyanazine Usage

By M.T. Meyer and E.M. Thurman

Abstract

Cyanazine is a chloro-s-triazine that was used as a pre-emergent herbicide prior to 1999 when its production was discontinued. The isopropyl-cyano group of cyanazine hydrolyzes rapidly to the amide and carboxylic-acid forming cyanazine amide and cyanazine acid, respectively. In addition, the modified isopropyl moieties are subject to biotic degradation forming deisopropylatrazine (DIA). In a field dissipation study that compared the unsaturated zone transport of atrazine and cyanazine, DIA was detected deeper in the soil profile from the cyanazine field plot than in the soil profile from the atrazine field plot. DIA was also detected deeper in the cyanazine field soil profile than cyanazine or cyanazine amide in the cyanazine field plot. These results indicate that during the sequential hydrolysis of the cyano group to the amide and the acid and also during unsaturated zone transport, the modified isopropyl moieties undergo biotic degradation to form DIA. In addition, the results indicate that the occurrence of DIA in the soil profile is from the transport and degradation of cyanazine acid. This hypothesis is supported by data from the atrazine field plot that show that DIA was not detected much deeper in the soil profile than atrazine. This suggests that DIA is degraded during unsaturated zone transport and thus, requires a parent source for its formation during unsaturated zone transport. The atrazine field plot data also show that deethylatrazine (DEA), a degradate of atrazine, was transported deeper into the soil profile than DIA indicating that it is more resistant to degradation. Thus, groundwater containing equal or greater concentrations of DIA than DEA may be a useful indicator of the prior use of cyanazine usage.

Meyer, M.T., and Thurman, E.M., 2004, Deisopropylatrazine in groundwater as an indicator of past cyanazine usage [abst.]: The Ninth Symposium on the Chemistry & Fate of Modern Pesticides, Vail, Colorado, August 16-19, 2004.

Additional information about cyanazine studies by the Organic Geochemistry Research Group in Kansas can be found at: http://ks.water.usgs.gov/researchlab.html

To request a paper copy of this abstract, email: mmeyer@usgs.gov

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