The coal industry, states and big business groups called the Obama administration’s rules for smog-forming ozone completely unattainable, laying out their legal arguments Friday in a heated case to upend what are called the most expensive regulations in history.

The decisions made by the Environmental Protection Agency in creating the rules are “arbitrary, capricious and contrary” to the Clean Air Act, the groups argue in a legal brief laying out their arguments against new ozone rules in the D.C. Circuit Court of Appeals.