Amiprophos-methyl (APM), a phosphoric amide herbicide, was previously reported to inhibit the in vitro polymerization of isolated plant tubulin (L.C. Morejohn, D.E. Fosket [1984] Science 224: 874-876), yet little other biochemical information exists concerning this compound. To characterize further the mechanism of action of APM, its interactions with tubulin and microtubules purified from cultured cells of tobacco (Nicofiana tabacum cv Bright Yellow-2) were investigated. Low micromolar concentrations of APM depolymerized preformed, taxol-stabilized tobacco microtubules. Remarkably, at the lowest APM concentration examined, many short microtubules were redistributed into fewer but 2.7-fold longer microtubules without a substantial decrease in total polymer mass, a result consistent with an end-to-end annealing of microtubules with enhanced kinetic properties. Quasi-equilibrium binding measurements showed that tobacco tubulin binds ['4C]oryzalin with high affinity to produce a tubulin-oryzalin complex having a dis- Phosphoric amide herbicides such as APM (Tokunol M) and butamiphos (Cremart) were developed as preemergence herbicides and are effective on annual grasses and broadleaf weeds (Aya et al., 1975). The uses of phosphoric amides are similar to those of the dinitroaniline herbicides, including