While Essex struggled to collect an underwhelming two batting points at Chelmsford, defending champions Surrey piled up six bonus points at the Oval in making Warwickshire follow-on to extend their advantage at present to 21 points.
Off-spinner de Caires, the 21-year-old son of Michael Atherton, might have returned even more spectacular figures, following on closely from his 7-144 against Hampshire in June, but Ryan Higgins spilled Dan Lawrence at slip and Mark Stoneman floored a chance at short midwicket that reprieved Adam Rossington, neither of which proved particularly costly.
Essex had looked in no trouble on a pitch that baked under a hot sun, with Nick Browne (59) and Sir Alastair Cook (58) putting on 122 for their first century opening stand of the season.
However, de Caires then took centre stage, helping reduce Essex initially to 169-5 inside 16 overs en route to 303-9 at the close.
Middlesex’s plight in the relegation mire was not helped by the news in the morning that the Indian off-spinner Jayant Yadav, signed initially for the last four Championship games, was stranded in Delhi because his visa documentation had not been completed in time at the British Embassy. Instead, the ball was thrown to de Caires from the ninth over and he bowled 38 overs from the River End with only a couple of breathers.
After winning the toss, Cook and Browne batted serenely in the fierce sunshine and without offering up a chance until de Caires let out a hopeful, though forlorn, shout to the last ball before lunch for lbw against Cook.
That turned out merely to herald a clatter of wickets. The young bowler was eventually rewarded with the prized scalp of Cook when the left-hander stuck his right leg down the wicket and was rapped on the pad to depart for 58 from 127 balls.
Cook had been first to fifty, reached from 89 balls with nine fours, followed by Browne from one more ball but one boundary fewer.
Before his own demise, the former England captain had lost Browne when a delivery from de Caires was flicked into the hands of short leg after a 108-ball 59.
De Caires had his third wicket in five post-lunch overs when he got a delivery to turn from outside off-stump, bamboozling Tom Westley and taking the middle-and-off bail.
Lawrence did not stay long before wafting at one down legside from Ethan Bamber, and Paul Walter withdrew his bat as one from de Caires went straight on and clipped off-stump.
However, a sixth-wicket stand of 66 in 18 overs between Matt Critchley and Rossington repaired the damage before Rossington picked out Luke Hollman on the long-leg boundary to provide de Caires with a fifth wicket. Critchley went in the next over for 36, lbw to Toby Roland-Jones.
Essex’s overseas addition, Indian fast bowler Umesh Yadav, marked his debut by striking de Caires for 14 runs from the first three balls of his 34th over but perished trying to land a second six over long leg.
When he returned after the new ball had been taken, de Caires had Simon Harmer caught heaving to short extra cover, before Sam Cook and Jamie Porter added another 24 to the total before the close.
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