Published online by Cambridge University Press: 12 June 2017
The influence of six Arkansas soils on the leaching characteristics of derivatives of 3-amino-2,5-dichlorobenzoic acid (amiben) and 3-nitro-2,5-dichlorobenzoic acid (hereinafter referred to as dinoben) in slotted soil columns was determined using large crabgrass [Digitaria sanguinalis (L.) Scop.] bioassay. The ammonium and aluminum salts of amiben and the sodium salt of dinoben were easily leached and leaching was not noticeably affected by soil type. The ammonium salt of amiben was not adsorbed, while the methyl ester of amiben was adsorbed by these soils. Adsorption was related to the clay and organic matter content of the soil. Methyl and butoxyethyl ester derivatives of amiben and dinoben resisted leaching in these soils and the amide of amiben was intermediate in leaching. The adsorption and leaching behavior of the ester derivatives of these compounds were complicated by their rapid hydrolysis in these soils. The hydrolyzed product behaved identically to the salt derivatives of the compounds in leaching, adsorption, and chromatographic properties. Hydrolysis of the methyl ester was inhibited by soil sterilization, dry soil, and temperatures below 20 C. In non-sterile, warm, moist soil, the half-life of the methyl ester of amiben was 28 hr. Four species of Bacillus were capable of hydrolyzing the methyl ester of amiben in pure culture studies.