What does it do?
iTunes Agent is a tiny application which rests in your system tray, constantly looking for devices being connected to your system. If a device it recognizes is connected it enables you to manage it via a playlist in iTunes. You may even associate your player with a Smart Playlist, such as "Party Shuffle", and always have a new collection of tracks on your player!
When you are done modifying the list of tracks for your player you can synchronize it with two small mouse-clicks!
iTunes Agent - At A Glance - Reviews by PC Magazine
This free open-source software is an excellent utility to help you sync your cell phone, PSP, or non-Apple MP3 player with iTunes.
Syncs iTunes songs and videos with most mass storage devices, including cell phones. Works with a wide variety of devices—even USB flash drives.
Doesn't work with lower-end phones and certain smartphones. Some Vista installation issues.
Get it at http://ita.sourceforge.net/