I’m suprised .22LR isn’t working.
However, at 30 to 50 yards, I’d just use deer slugs in the .410.
If he’s hitting them with the .22 it’s probably working but not immediately. Might as well put them down humanely with something that does the job right.
“Im suprised .22LR isnt working.”
Hollow points probably would but I would go for something with a little more impact.