In my neck of the woods (4b) it would likely be late-July to early-August. It would be nice to plant the brassicas and free rye together but if I waited that long here I would not get enough growth on my brassicas before our first average frost date (around Sept 10). I like to get at least 60 days growth on brassicas before then so I plant them in early July. At that time the rye seed isn't viable yet so I have to broadcast my rye later. I'm sure the dates will vary from year to year depending upon soil moisture, temps, etc. The only way to really know for sure is to do a rag doll test I suppose.
June 6th - not a chance ...
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July 5th - Nope...
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July 15th - Nope, not yet...
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July 21 - Now we are getting some place...
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Let's do a rag doll test (wrap the seed in a moist paper towel, insert it in a plastic baggie and set it out in the sun)
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A week - 10 days later I see I got about 35%-40% germination from the seed collected on July 26th, so I could have mowed the rye and planted the brassicas that day and would have had some rye germinate but not too much which might crowd out the brassicas. This would probably work for me but the growth on my brassicas would suffer some if I planted them that late so I opt to plant early when the rye seed isn't viable yet and then broadcast rye a few weeks later. This may well work though, depending upon your latitude and weather. (there was a little Hairy Vetch seed in there too, which did not germinate)
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By comparison, here is a cover crop of rye which I mowed on August 13th. (I can't remember what rate I drilled it at but it looks pretty thick - maybe 60#/acre)
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15 days later on August 28th I have a very thick crop of volunteer rye coming up which would have really crowded brassicas if I had planted them at the same time.
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