Asian stocks fell, dragged down by energy-related shares as oil prices hit their lowest levels since 2009.
The price of West Texas crude dropped 5.8% to $37.65 a barrel, while Brent Crude fell 5.3% to $40.73.
Oil prices have been hit after Opec – the oil producers’ cartel – failed to cut production last week.
Japan’s Nikkei 225 closed down 1% at 19,492.6, despite figures showing that Japan’s economy avoided a technical recession in the third quarter.
Shares in troubled Japanese tech giant Toshiba ended 3% lower following the news that the firm could face a record fine of 7.37bn yen ($60m; £39m) for its multi-billion dollar accounting scandal.
Fifty individual Toshiba shareholders are also seeking $2.45m in damages from the firm after its stock plunged following the accounting scandal.