Hi Bridie,
One way you could achieve this would be to remove the learner as attendee and then re-add them to the event.
To do this to go to the Seminar activity and select the seminar event where you want to re-notify the manager. Next you'll need to click the "Actions drop down" and click remove attendees.
Select the attendee whose manager has lost the the original approval email and remove them from the seminar.
At this stage to prevent unwanted notifications being sent, you'll probably want to suppress the cancellation notices by un-checking the "Notify cancelled attendees" & "Notify cancelled attendees' manager".
Finally re-add the attendee to the seminar. This will re-trigger the booking request and approval notification to be sent to the manager.
I hope this is helpful, let me know if you need more assistance.