Japan`s stocks led losses across much of Asia as oil prices continued to slide and with investors remaining cautious ahead of a widely-expected US interest rate rise this week.
The benchmark Nikkei 225 closed down 1.8% at 18,883.42.
The index fell 3% in earlier trade as the yen gained against the dollar.
A stronger yen makes Japan`s exports more expensive to buy overseas and hurts exporters when they repatriate their earnings.
Meanwhile, a better-than-expected business sentiment survey from the Bank of Japan failed to boost investor sentiment.
The closely watched Tankan index showed sentiment at major companies was unchanged at +12 for the fourth quarter.
Capital Economics` Marcel Thieliant said the index had been expected to weaken.
"Business conditions for non-manufacturing firms were unchanged [and] remained the strongest they have been since the early 1990s," he said.
Elsewhere, Australia`s benchmark S&P/ASX 200 closed down 2% at 4,928.60 as energy-related stocks dragged on the market.
"The key factor affecting the market at the moment is the continuing oversupply of oil," said Gary Huxtable of Atlantic Pacific Securities. "It is dragging energy stocks down."
Hong Kong`s Hang Seng was down as much as 2.5% in early trade, but recovered some ground in the afternoon to close down 0.7% at 21,309.85.
Hong Kong-listed shares in Fosun International, the parent company of Shanghai-based Fosun Group, fell by nearly 10% on Monday. Trading in the firm`s shares had been halted on Friday amid reports that its chairman, Guo Guangchang, was missing.
Reports later on Friday said Mr Guo, a high-profile Chinese tycoon, had been detained by police and was assisting authorities with an investigation. Mr Guo appeared at his company`s annual meeting in Shanghai on Monday.
The Shanghai Composite was the one bright spot in the region, closing up 2.5% at 3,520.67 as investors cheered positive economic data out of Beijing over the weekend.
South Korea`s Kospi index closed down 1.07% at 1,927.82.
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