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Luis Montenegro leaves parliament after the vote /REUTERS
Portugal's centre-right minority government has lost a vote of confidence, putting the country on track for its third election in three years.
Prime Minister Luis Montenegro, who has served for 11 months, called the vote after concerns over his family business dealings.
Montenegro has denied wrongdoing.
"The insinuation that I mixed my business and political activity is completely abusive, and even insulting. A repeated falsehood does not become the truth, but it contaminates the political environment... this is what populism feeds on," he told parliament before the vote.
Nevertheless, he lost the confidence vote 142-88.
President Marcelo Rebelo de Sousa will decide whether a new government can be formed without elections, which might otherwise take place in mid-May.
Opinion polls put Montenegro's Democratic Alliance party level with the opposition socialists.