Due to the increasing use of chlorinated organic compounds, environmental pollution is a key issue in agricultural and industrial areas. In this study, biodegradation of chloroacetanilide herbicides, such as alachlor and metolachlor, by eight fungal strains of Trichoderma spp. originating from different microorganism collections was investigated. The tested fungi converted 80–99% of alachlor and 40–79% of metolachlor after 7 days of incubation. Biotransformation of herbicides was performed mainly by dechlorination and hydroxylation reactions. Eight alachlor metabolites and four byproducts of metolachlor conversion were detected in Trichoderma cultures, including two metolachlor intermediates for the first time identified in fungi. Moreover, in the cultures of six Trichoderma strains supplemented with chloroacetanilides, a decrease in toxicity was observed toward tested Artemia franciscana crustaceans. Simultaneously, 7 days after the application of the spores of T. koningii IM 0956, T. citrinoviride IM 6325, T. harzianum KKP 534, T. viride KKP 792 and T. virens DSM 1963 the length of roots and shoots of rapeseed seedlings treated with alachlor or metolachlor significantly increased. All tested strains exhibited plant growth-promoting traits, such as siderophore production, 1-aminocyclopropane-1-carboxylate deaminase (ACCD) activity, and phosphate solubilization, even in the presence of chloroacetanilide herbicides.