Imidazolinone herbicides are a group of chiral herbicides that are widely used to control weeds in crops. Despite their wide use, few studies on the behavior of enantiomers in terrestrial systems have been reported. In this study, the bioaccumulation of imazamox, imazapic, and imazethapyr enantiomers in earthworm and their degradation in soils were assessed using earthworm-soil microcosms. The bioaccumulation of the three herbicides in earthworm was not significantly enantioselective. Imazamox and imazethapyr did not significant stereoselective degradation in soil (p > 0.05), while the enantioselectivity of the degradation of imazapic was significant (p < 0.05). Furthermore, biota to soil accumulation factor (BSAF) values were also calculated for three herbicides. Relationships between BSAF values and organic matter content of soil and log KOW of herbicides were investigated. The BSAFs values were negatively correlated with the log KOW of herbicides, and were positively correlated with organic matter content of soil in earthworm-soil microcosms. These relationships indicated that chemical hydrophobicity (Kow) and organic matter content of soil were good predictors to estimate the bioavailability of imidazolinone herbicides to earthworm.