Update / synchronize itunes library automatically and manually

hello,
i am using i tune to transfer my data from my pc to ipod but the problem is proper synchronization at most event my brother lost all data due to automatic synchronization so please tell me that how can i do that mannually or automatically without loss of any data from ipod. well itune features all useful functions except media updating. what must do with iTune to make it select new tracks from selected folders and automatically add them to the media library.please can some one help me ?
thank you

you can work with third party application like SuperSync 3.0 iTunes Music Library Synchronization Software this will allow you new playlist viewer and improved playlist synchronization.

try iTunes Folder Watch with this New files imported into iTunes can be organized automatically into iTunes playlists if required. This makes it very easy to find and browse your new music or videos. The Configuration tab gives full control over all the features also it can be run as a taskbar process and so will continually monitor folders.