Thank you for contacting MSU Extension.  I apologize for not getting back with you sooner.  The short answer is that your trees appear to be under considerable stress, which can be for a variety of reasons.  The holes in the trunk appear to be from a combination of bark beetles, wood borers, and woodpeckers chasing after the insects tunneling under the bark.  I will get back to you with more information in the next day or so.  Thanks for your patience!

I apologize again for the delay in responding to your question.  Pines can go into decline for a variety of reasons.  Frequently, there is something in the environment that is stressful to the tree.  For example, trees require 1 inch of water per week as rain or by supplemental irrigation.  During prolonged periods of drought, the tree will become stressed.  If the soil has dried out too much, the fine roots that are responsible for taking up water and nutrient can die, making water uptake more difficult. Treatment would be irrigating during dry periods and applying 2 - 3 inches of mulch (clean needles, wood chips, etc.) to conserve soil moisture.  

Any stress can make a tree more susceptible to insects or disease.  Other factors that can stress a tree include soil compaction, wet soil, improper planting, construction, and winter injury.  Stressed pines also become highly attractive to bark beetles and other wood boring insects, which are evident from the photos.  

Pines that appear near death, with large amounts of needle loss, are unlikely to recover.  Others may be saved by determining the causes of stress and taking steps to mitigate that stress.

For more information:

Why are my pine trees turning brown?

Pine borers

Red pine decline

Trees and drought

Cold injury in conifers

To find a certified arborist to look at your trees: Find an arborist tool

You could consider sending a sample to Michigan State University’s Plant and Pest Diagnostics for a health check and recommendations.

Neither of those chemicals would be helpful at this time of the year, and are likely to kill beneficial insects that contact them. Next year, application of insecticide to the trunk and branches during the life stage where the adult insects are flying can control many borers, but you have to time the spray to coincide with the flight time of the adults. 

Any trees that have half of their branches covered in completely brown needles will not recover, and should be removed by April 1, before borers exit the tree. They can be used for firewood, chipped, or buried. You could try a soil drench of imidacloprid this fall on remaining trees, used exactly according to the label. Sanitation is key, removing and disposing of dead trees and branches.