I am converting this to a bug as it is more related to a missing event in the contextMenu option.
Generally, in order to toggle specific tools you need to handle the open event of the ContextMenu and depending on the target to programmatically toggle the tool via the enable method. However. due to emission in the FileManagerContextMenu class, the open event is not directly available. It is needed to be added to the events field first. And this the bug here (https://github.com/telerik/kendo-ui-core/issues/5530).