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For heavy metal-contaminated agricultural land, low-cost, plant-based phytoextraction measures can be a key element for a new land management strategy. When agents are applied into the soil, the solubility of heavy metals and their subsequent accumulation by plants can be increased, and, therefore, phytoextraction enhanced. An overview is given of the state of the art of enhancing heavy metal solubility in soils, increasing the heavy metal accumulation of several high-biomass-yielding and metal-tolerant plants, and the effect of these measures on the risk of heavy metal leaching. Several organic as well as inorganic agents can effectively and specifically increase solubility and, therefore, accumulation of heavy metals by several plant species. Crops like willow (Salix viminalis L.), Indian mustard [Brassica juncea (L.) Czern.], corn (Zea mays L.), and sunflower (Helianthus annuus L.) show high tolerance to heavy metals and are, therefore, to a certain extent able to use the surpluses that originate from soil manipulation. More than 100-fold increases of lead concentrations in the biomass of crops were reported, when ethylenediaminetetraacetic acid (EDTA) was applied to contaminated soils. Uranium concentrations could be strongly increased when citric acid was applied. Cadmium and zinc concentrations could be enhanced by inorganic agents like elemental sulfur or ammonium sulfate. However, leaching of heavy metals due to increased mobility in soils cannot be excluded. Thus, implementation on the field scale must consider measures to minimize leaching. So, the application of more than 1 g EDTA kg(-1) becomes inefficient as lead concentration in crops is not enhanced and leaching rate increases. Moreover, for large-scale applications, agricultural measures as placement of agents, dosage splitting, the kind and amount of agents applied, and the soil properties are important factors governing plant growth, heavy metal concentrations, and leaching rates. Effective prevention of leaching, breeding of new plant material, and use of the contaminated biomass (e.g., as biofuels) will be crucial for the acceptance and the economic breakthrough of enhanced phytoextraction.