Photosynthesis inhibition by phenylureas: a QSAR approach

A series of 21 N'-phenyl-N,N-disubstituted ureas was studied for its effects on thylakoidal electron transfer, photophosphorylation, and photosynthetic O2 evolution in class A chloroplasts and leaf fragments. The concentrations of test compounds that produced 50% inhibition of PS II electron transfer and of photosynthesis in class A chloroplasts were highly correlated. Urea derivatives with a N-lipophilic substituent (three or four carbon chains) were uncouplers (i.e., neburon uncoupled by 50% at 7 microM). The efficiency of inhibition of PS II electron transfer was increased by the presence of a 3,4-disubstitution of the phenyl ring. The presence of N-lipophilic substituents was necessary for there to be an inhibitory effect, but an increase in the length of the chain lowered the activity. The best QSAR equations that described the inhibitory activity of the whole series were obtained when using 1 chi v or MR (probably representing dispersion forces) associated with parameters that described the steric hindrance at the p position of the phenyl ring (Verloop's B2(4), B4(4)) or in its neighborhood (such as the angular parameter A4). The inhibitory efficiency of the phenylurea series on wheat and spinach pieces led to the conclusion that some extrachloroplastic factors seemed to limit the accessibility of the D1-protein target.