To assess the impact of phthalates on soil microorganisms and to supplement the environmental risk assessment for these xenobiotics, soil was treated with diethyl phthalate (DEP) or di (2-ethyl hexyl) phthalate (DEHP) at 0.1 to 100 mg/g. Bioavailability and membrane disruption were proposed as the characteristics responsible for the observed fate and toxicity of both compounds. Diethyl phthalate was biodegraded rapidly in soil with a half-life (t 50 deg) of 0.75 d at 20ЊC, and was not expected to persist in the environment. The DEHP, although biodegradable in aqueous solution (t 50 deg Ͻ 15 d at 20ЊC), was recalcitrant in soil, because of poor bioavailability (only 10% degraded by 70 d at 20ЊC) and was predicted to account for the majority of phthalate contamination in the environment. Addition of DEP or DEHP to soil at a concentration similar to that detected in nonindustrial environments (0.1 mg/g) had no impact on the structural diversity (bacterial numbers, fatty acid methyl ester analysis) or functional diversity (BIOLOG) of the microbial community. At concentrations representative of a phthalate spill, DEP (Ͼ1 mg/g) reduced numbers of both total culturable bacteria (by 47%) and pseudomonads (by 62%) within 1 d. This was due to disruption of membrane fluidity by the lipophilic phthalate, a mechanism not previously attributed to phthalates. However, DEHP had no effect on the microbial community or membrane fluidity, even at 100 mg/g, and was predicted to have no impact on microbial communities in the environment.