1. Mantua, Francesco II. Compare the reverse image + lettering with these ones: N#319888 and N#538644. Although I couldn't find this smaller denomination, copper coin in Numista.
2. Maybe Bologna? There are similar coins with the double keys (N#489874) and with the crowned eagle (N#481868).
Good catch. The Mantua Quattrino didn't come up in my search. I usually filter out everything except the circulation and circulation commemoratives, which backfired in this instance as it is not registered as a standard circulation coin. Opened a change request to fix it.