How to Kill Large Oleander

Wear protective eyeglasses and gloves to prevent direct contact with the sap. Spread tarps under the large oleander shrub onto which the clippings will fall. Use as many tarps as needed to cover the soil under the shrub and extend 12 to 15 inches beyond its foliage.

Cut back large limbs from the tree using a pruning saw, or use lopper pruners to cut off smaller limbs. Position the saw flush against the trunk and slice the limb off, allowing it to fall on the tarp. Start from one corner of the shrub and work your way around it to remove all the growth, thereby reducing the weight on the trunk.

Cut the main trunk into sections, starting at the top of the shrub and working your way down toward the bottom, leaving a stump that rises 6 inches above the soil. Grasp the chainsaw firmly with your hand and maintain steady pressure as you slice the trunk into sections.

Brush the exposed surface of the stump to remove sawdust, since it may prevent the movement of the herbicide to the roots.

Drill a series of 12-inch-deep holes through the top and sides of the stump. Position these 1-inch-wide holes 4 inches from the edge of the stump.

Fill a long spouted plastic container with glyphosate herbicide. Position the spout directly above each hole and pour 3 to 4 ounces of the herbicide in it. The herbicide translocates to the roots, killing them within six to eight weeks.

Insert a shovel in the ground, 2 to 3 feet away from the base of the stump. Dig a trench around the perimeter of the stump, making it 10 to 12 inches deep. Angle the shovel under the soil ball to slide it under the dead or dying root ball and pry it out of the soil.

Chop exposed roots with a hatchet as you work. Continue to force the shovel under the root ball until you release it from the soil. Grasp the stump and lift it out of the soil, with an assistant.

Collect the broken root pieces and debris from the hole in the soil and refill it with fresh soil.