By looking at the date format and syntax, my quess is you are using Oracle. I have found problems using the Oracle default date format with comparisons. What I tend to do in DBI code is set the date format with an alter session, usually right after the connect,

   my $dbh = DBI->connect();
      $dbh->do('alter session set nls_date_format = 'YYYYMMDD');
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This sets the date format for the whole session. Then you can do compares with an easier format, select id from foo where date < 20001201; ..This also makes it easy to format a data file which may be read in for updates or comparisons to a db.

STH