The uptake of the organophosphates tris(2-chloroethyl) phosphate (TCEP), tris(1-chloro-2-propyl) phosphate (TCPP), tributyl phosphate (TBP), the insect repellant N,N-diethyl toluamide (DEET), and the plasticizer n-butyl benzenesulfonamide (NBBS) into plants was studied in greenhouse experiments and simulated with a dynamic physiological plant uptake model. The calibrated model was coupled to a tipping buckets soil transport model and a field scenario with sewage sludge application was simulated. High uptake of the polar, low-volatile compounds TCEP, TCPP, and DEET into plants was found, with highest concentrations in straw (leaves and stem). Uptake into carrot roots was high for TCPP and TBP. NBBS showed no high uptake but was rapidly degraded. Uptake into barley seeds was small. The pattern and levels of uptake could be reproduced by the model simulations, which indicates mainly passive uptake and transport (i.e., by the transpiration stream, with the water) into and within the plants. Also the field simulations predicted a high uptake from soil into plants of TCEP, TCPP, and DEET, while TBP is more likely taken up from air. The BCF values measured and calculated in the greenhouse study are in most cases comparable to the calculated values of the field scenario, which demonstrates that greenhouse studies can be suitable for predicting the behavior of chemicals in the field. Organophosphates have a high potential for bioaccumulation in crops and reach agricultural fields both via sewage sludge and by atmospheric deposition.