The 30-share barometer, which lost 185 points in the previous day's trading, declined further by 248.45 points to 14,048.34, a level last seen on July 30.
The wide-based National Stock Exchange's Nifty also lost 78.10 points to end the day at 4,214.00.
Marketmen said selling pressure picked up ahead of the release of inflation data this evening amid reports that the crude oil prices gained fresh ground.
Investors squaring up their pending long positions on expiry of August contract in the derivative segment also aided the weak trend.
Oil and gas segment stocks suffered the most on surging crude prices. The sector's index fell sharply by 247.81 points at 9,407.79, after sector major Reliance Industries dropped by Rs 74.15 at Rs 2,073.70 and its subsidiary Reliance Petro by Rs 3.45 at Rs 154.50.
Capital goods index fell by 262.37 points at 11,492.50 followed by metal index by 224.79 at 11,925.15 as heavy-weight stocks of Tata Steel, Sesa Goa, Jindal Steel and SAIL lost substantial ground.
PSU index fell by 125.11 points at 6508.16, bank index by 119.04 points at 6596.41, realty index by 83.97 points at 4753.07, Information Technology index by 38.78 points at 3853.39, power index by 33.90 points at 2516.41, Teck index by 33.89 points at 2980.28, healthcare index by 20.92 points at 4273.57, consumer durables by 17.77 points at 3748.84 and FMCG index by 12.18 points at 2169.98.
As the selling pressure extended in all the sectors, small-cap index fell by 77.61 points at 6782.30 and mid-cap index by 77.58 points at 5608.85.