You should try to break your problem up into smaller segments which you can more easily solve. First you need to search your file1 and pull out the information in an array. Once you have that solved, then you can use something like the following to do the multiple mailling. Is it absolutely neccessary that you do this using the "mail" program? Perl has modules which allow you to do it all in one script. For example, here is an untested script to show the idea.

#!/usr/bin/perl
use warnings;
use strict;
use MIME::Lite;

# In the first part of the script you would search your file1
# and place your recipients and other info into an array.
# I leave that part to you, please show some code, as this
# is an educational site, not a script writing service

my $filename = 'foobar.pdf'; 
my @recipients= ( "tfxo@gmail.com", "bob@sss.com", "z@zed.net"  );

foreach my $recipient( @recipients ){
  sendmsg( 'your@emailaddress', $recipient,  'the subject',  'body_tex
+t',  $filename );
 }

sub sendmsg {
my ( $From_Addr, $Mail_Name,  $Subj_Text, $Body_Text, $File_Name ) = @
+_;

$MIME::Lite::AUTO_CONTENT_TYPE="true";

my $msg = MIME::Lite->new(
 From =>$From_Addr,
 To =>$Mail_Name,
 Subject =>$Subj_Text,
 Type =>'multipart/mixed',
);

$msg->attach(Type=>'TEXT',
  Data=>$Body_Text,
);


$msg->attach(Type=>'application/octet-stream',
          Path => './mailbody' ,
          Filename => $File_Name
);

MIME::Lite->send('smtp', "mail.somewhere.net", Timeout=>60);
}
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