Apple replant is a widespread agricultural problem documented in all of the major fruit-growing regions of the world. In order to better understand the phytotoxic mechanisms induced by allelochemicals involved with this problem, Malus prunifolia plants were grown hydroponically to the six-leaf-stage in the presence of phthalic acid (0 or 1 mM) for 5, 10, or 15 days. Apple plants were evaluated for: shoot and root length, fresh and dry weight, malondialdehyde (MDA) content, hydrogen peroxide (H(2)O(2)) content, superoxide radical (O(2) (*-)) generation rate, and antioxidant enzyme activities. Shoot and root lengths and fresh and dry weights of M. prunifolia decreased in plants exposed to phthalic acid. MDA and H(2)O(2) content increased in phthalic acid-treated plants as did the generation rate of O(2) (*-) in M. prunifolia roots. The activities of superoxide dismutase (EC 1.15.1.1), peroxidase (EC 1.11.1.7), catalase (EC 1.11.1.6), ascorbate peroxidase (EC 1.11.1.11), glutathione reductase (EC 1.6.4.2), dehydroascorbate reductase (EC 1.8.5.1), and monodehydroascorbate reductase (EC 1.6.5.4) increased in phthalic acid-stressed roots compared with control roots. These results suggest that activation of the antioxidant system by phthalic acid led to the formation of reactive oxygen species that resulted in cellular damage and the decrease of M. prunifolia growth.