This is a hack I used to solve this issue in our application:
private static HttpWebRequest CreateWebRequest(Uri uri)
{
//Webrequest creation does fail on MONO randomly when using WebRequest.Create
//the issue occurs in the GetCreator method here: http://www.oschina.net/code/explore/mono-2.8.1/mcs/class/System/System.Net/WebRequest.cs
var type = Type.GetType("System.Net.HttpRequestCreator, System, Version=4.0.0.0,Culture=neutral, PublicKeyToken=b77a5c561934e089");
var creator = Activator.CreateInstance(type,nonPublic:true) as IWebRequestCreate;
return creator.Create(uri) as HttpWebRequest;
}