Horsehead Holding Corp. yesterday filed for Chapter 11 bankruptcy protection, a little more than a month after the Pittsburgh-based manufacturer missed a $1.9 million payment and saw its stock plummet more than 90 percent, the Pittsburgh Business Times reported today. Horsehead filed for chapter 11 in the U.S. Bankruptcy Court for the District of Delaware listing liabilities of $544.7 million and total assets of $1 billion. Its biggest unsecured claims are a $100 million unsecured convertible note and a $400 million unsecured convertible note, both administered by U.S. Bank National Association, according to a bankruptcy filing. It had about $1 million in cash and applied for permission for $90 million in debtor-in-possession financing.