IMO, and you know Marksr will be along shortly with the good advice, Silicone is never a good exterior product. Sun and weather take it's toll on it. I prefer to use an elastomeric caulk where two planes collide, such as at brick mold or window molding. Let's wait on Mark to chime in here.
Is this a door? Take another picture from farther away so we can see an overall view. If it is a door, buy a new prehung door and fill that slot with mortar.
Personally, I think I'd pop off a few of the sill bricks and remortar them so that they have a nice 3/8-1/2 gap between each of them. By the time you do that to 4 or 5 of them you will have spread the bricks out enough that you won't have any more gap... other than the same 3/8-1/2 mortar joint that you should have on the ends. As for the rotten wood above the brick sill, it looks like all you need to do is remove the storm door z-bar and replace the face trim. The sill nose looks fine. The board on the side of the bricks shouldn't even be there. A wider picture maybe would give us a better idea why its there.
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