Bank of America executives were so concerned about the worsening financial condition of Merrill Lynch last year that they sought legal advice about the applicability of a “material adverse change” clause before the December 5 shareholder vote on the acquisition, a state regulator said on Tuesday.

The disclosure by the office of Andrew Cuomo, New York attorney-general, raises questions involving BofA’s public explanation about its concern over growing losses at Merrill, which the bank says only reached a crisis level in the second week of December.