What are these?

I recently bought a collection of router buts from an old woodworkers estate. All together, there were close to 200 bits. They ranged from old Stanley steel bits to newer carbide bits. In the group were 10 that I cannot identify. They may not even be router bits. Can anyone help identify these and maybe tell me ho they were used?

Wood Machinery & Supplies

3D space planning platform

2020 Ideal Spaces is a cloud-based 3D space planning solution that provides an industry platform enabling omnichannel retail for consumers, home centers, retailers, and manufacturers. improves the consumer onboarding experience through every step of the buying journey, from inspiration to qualification to space planning to purchasing—resulting in higher qualified leads and conversions.