Business confidence in Germany fell in November to the lowest level since 1993, according to the key Ifo economic climate index.
The index, based on a poll of 7,000 companies, has dropped for six consecutive months, the Munich-based Ifo institute said.
The index stands now at 85.8, down 4.4 points from October.
"The downturn has worsened and will now have an impact on the labour market", Ifo said in a statement.
Germany's exports have been hard hit by falling demand worldwide, with some auto makers seeking state help to maintain production.
On Friday another key indicator, the Markit purchasing managers' index, revealed that business activity in the 15 countries sharing the euro had fallen in November to a ten-year low.
The index showed that the deterioration in economic climate was felt by all sectors, with output, new orders, outstanding business and purchasing activity all falling to record lows.
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