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NEW YORK — Shades of the roiling energy markets that were set off last year by the crisis on Wall Street emerged again Friday with crude seeing the largest percentage drop in prices since January.

The sell-off this time followed troubling news from Dubai, which asked lenders for a six-month reprieve on payments for about $60 billion in debt.

Benchmark crude prices plunged by 7 percent in early trading, though those declines eased as investors weighed the chances that Dubai’s problems would spread to Europe, Asia and the United States.

Benchmark crude for January delivery fell $1.91 to settle at $76.05 on Nymex.

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