OK lets get this sh*t straight!
"DETONATION" and "PREIGNITION" are not!, never have been!, and never will be the same thing!!!
A fuels "octain" rating is it's RESISTANCE to burning, the higher the octain the harder it is to ignite and the slower it burns, higher compression engines need higher octain fuel because of the compression pressure, the higher the pressure the HOTTER the air fuel mixture gets, if it's hotter it'll burn faster, you want "PEAK" burn to occur at a few degrees before TDC (top dead center) and fallow threw a few degrees after TDC, this is where ignition timing comes in, it set to make this event occur at the optimal time.
So basically detonation is fuel that reaches peak burn BEFORE the piston reaches TDC, so the piston, crank and rod have to fight the force rather than use it!, it usually breaks ring lands and piston crowns!
Preignition is when the air/fuel mixture gets ignited by a source other than the spark plug, usually a sharp edge or a carbon deposit that's glowing enough to touch off the mixture.
Both are BAD!
As for the oil in the crank case, FastLANE got it close, the seal on the crank could also be worn out, the vacuum from the crank case could be pulling tranny oil into the case thrue the worn seal!?, make sure the vent hose is not pinched or plugged?