A Moscow court on Monday issued an arrest warrant on charges of murder for Leonid Nevzlin, a key shareholder in Yukos and one of the closest associates of Mikhail Khodorkovsky, the oil company’s former chief executive.

Leonid Nevzlin fled to Israel last year as investigations into Yukos started to intensify and now has an Israeli passport. Earlier this year he was charged with tax evasion and embezzlement.

Russian prosecutors have now accused him of organising contract killings and assassination attempts on several people, including Yukos’s competitors.

The fresh allegations come at a crucial time for Yukos and Mr Khodorkovsky. The company could be dismantled and forced into bankruptcy in weeks if the Ministry of Justice proceeds with the sale of its main production asset to settle a $3.4bn tax bill.

Mr Khodorkovsky is standing trial for fraud and tax evasion and faces a 10-year prison sentence if found guilty. He entrusted Mr Nevzlin with his Yukos stake on his arrest.

The new charges against Mr Nevzlin further diminished investors’ hopes of a deal between the company and the government. Yukos shares fell more than 20 per cent to $4.20 on Monday, and have fallen nearly 50 per cent since last week.

The prosecutor general’s office said it had gathered “enough evidence . . . that . . . Mr Nevzlin conspired with A[leksei] Pichugin, the head of the internal and economic security department of Yukos, to kill particular individuals who represented a threat to the company as well as to Mr Nevzlin and Mr Pichugin”.

Mr Pichugin, a former KGB operative, was arrested more than a year ago and accused of murder and attempted murder. Prosecutors now say he acted on Mr Nevzlin’s instructions. They say Mr Nevzlin had arranged for Mr Pichugin to kill a married couple because they feared the husband could blackmail them with evidence of other crimes. The couple’s bodies were never found.

Mr Nevzlin is also accused of organising an attempt to kill Yevgeny Rybin, the head of East Petroleum, who allegedly threatened Yukos with international law suits for a breach of contract. Mr Rybin escaped the attempt but his driver was killed.

An Israeli justice ministry spokesman said an extradition treaty existed between Israel and Russia and that, if a request were received from the Moscow authorities, police would be ordered to locate the suspect

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