The application of agricultural chemicals (fertilizers, pesticides, herbicides, etc.) leads to carbamate ester contamination in soil. N,N,-diisopropyl- (1) and N,N,-diallyl- (2) carbamoyl chlorides are found in substituted heterocyclic tetrazolinone compounds used for controlling harmful organisms. Their environmental accumulation poses a potential ecosystem risk due to direct or indirect exposure. For substrates 1 and 2, detailed kinetic studies using advanced techniques first determined their pseudo-first-order rate constants which were then used in linear free energy relationships to understand the (mixed) solvent effects. For 1 and 2, we obtained l/m (bond making/bond breaking) ratios of 0.73 and 0.57 respectively. The ratios are useful for assigning (breakdown) mechanism and are found to be in line with the l/m ratios of other disubstituted alkyl-, aryl-, or alkylaryl- carbamoyl chlorides. Soil microorganisms are capable of metabolizing (hydrolyzing) carbamates and can easily adapt themselves to metabolize the different types of carbamates. The ability ofEscherichia coli, a model Gram-negative bacterium, to grow in the presence of substrates 1 and 2 were determined. While no effects were observed when grown in complex media (Mueller-Hinton broth), some suppression of growth was observed in minimal media (M9 minimal media).

Evaluating the long-term environmental impacts of carbamic acid derivatives

2019 Spring National Meeting

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