(AP) — Delaware's Supreme Court has refused to hear an appeal by insurers who may be on the hook for $190 million for lawsuits stemming from a 2013 buyout in which Dole Food chairman and CEO David Murdock took the company private.

The court refused Friday to consider an appeal of a judge's ruling that Delaware law allows a company to insure officers and directors from any liability — including for fraudulent acts.

A Delaware judge in 2015 ordered Murdock and former Dole president and COO C. Michael Carter to pay $148 million for misleading directors and shareholders in the $1.2 billion buyout, saying they acted fraudulently and in bad faith.

A settlement reduced that amount to about $116 million. Murdock agreed to pay $74 million to settle a separate federal lawsuit.