Assessing N,N‘-Dibutylurea (DBU) Formation in Soils after Application of n-Butylisocyanate and Benlate Fungicides

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Abstract
N,N'-Dibutylurea (DBU) is a breakdown product of benomyl [methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate], the active ingredient in Benlate fungicides, and has been proposed as one cause for crop damage that growers claim to have occurred from the use of Benlate 50 DF fungicide. This study assessed DBU formation upon (1). application of n-butyl-1-[(14)C]butylisocyanate (BIC), the immediate precursor to DBU formation, in four soils at two water potentials (0.03 and 0.1 MPa) and (2). application of benomyl butyl-1-(14)C-benomyl enriched Benlate DF and SP fungicides to two soils at various combinations of negative water potential (0.03 or 0.1 MPa) and temperature (23 or 33 degrees C). Parent compounds, metabolites, and (14)CO(2) were tracked using chromatographic analysis with radioassay and UV detection, liquid scintillation counting, and postextraction oxidation of the soil. At 0.03 MPa in all four BIC-treated soils, DBU formation was never detected. At 0.1 MPa, DBU was detected in two soils, but at concentrations <3.6 microg kg(-)(1) (0.3 wt % of applied BIC). In both soils treated with benomyl formulations, DBU formation was observed with only Benlate 50 DF application at 0.03 MPa and 23 degrees C, which was followed by rapid dissipation of DBU. The maximum concentration observed was 0.41 microg g(-)(1) (0.65 wt % of applied benomyl at 62.8 microg g(-)(1)), which is well below levels currently reported to cause adverse effects to plants. Combined benomyl and carbendazim half-lives in soils across treatments were 2-3 months. This study demonstrated that further production and accumulation of DBU in soils after Benlate application or from residual benomyl remaining in the soil are highly unlikely and that persistence of any DBU in soils is likely to be short-lived.