The Pensions Regulator (TPR) has issued a £382,136 contribution notice to a man who purchased steel wire company Carrington Wire for £1.
Richard Williams was the "third target" with a contribution notice following an investigation into the firm's defined benefit (DB) pension scheme.
In February, the other two targets - Russian metal companies PAO Severstal and OAO Severstal-Metiz - agreed to pay a settlement of £8.5m to the pension scheme.
Yorkshire-based Carrington Wire was closed down in 2010, but its liability to the scheme remains.
TPR said the two Russian firms, which owned Carrington Wire, entered into negotiations with Williams, sole director and shareholder of a shell company called Gillico for the sale of Carrington Wire for £1. The regulator also said Williams benefited from £400,000 paid by the Russian firms.
TPR and the trustees were informed of the sale after it had happened. According to the regulator, the sale meant the scheme lost the benefit of the guarantee.
TPR asked its determination panel to issue a contribution notice of £382,136 against Williams.
Stephen Soper, executive director for DB at TPR, said: "The conclusion of this complex case demonstrates that the regulator will, where appropriate, pursue its avoidance powers to seek to help protect member benefits, including in cases where targets are based overseas."
TPR said the settlement and the funds sought from the third target would not be enough for the scheme to avoid entering into the Pension Protection Fund.
Simon Taylor, partner at Barnett Waddingham LLP, said: "In this case, TPR holds that it was reasonable to seek payment of nearly £400,000 from the individual who purchased Carrington Wire Limited in 2010. The amount may seem a drop in the lake compared to the £8.5m TPR was able to obtain from the Russian companies, but shows that TPR is willing to pursue all avenues to make sure each pension scheme gets its dues. This highlights the importance of undertaking proper due diligence in any corporate transaction where there is a pension scheme involved.
"Unfortunately, the pension scheme members will not benefit directly from TPR's efforts. The scheme will still fall into the Pension Protection Fund, and members will get less than their expected scheme benefits as a result."