Prosecutors in a landmark trial against Google on Wednesday asked for jail terms ranging from six months to a year over a video posted in 2006 of an Italian teenager with Down's Syndrome being bullied in school.

It is the first trial anywhere against executives of the Internet search engine company, which strongly denies the charges. Experts say it could have implications for the way Google operates in Italy and for the wider debate over freedom of speech and legal responsibility for Internet postings.

Former Google Italy president David Carl Drummond, now senior vice president, faces a one-year term along with George De Los Reyes, a retired former Google Italy board member, and Peter Fleitcher, Google Europe's privacy strategy chief.

Arvind Desikan, head of the Google Video for Europe project, faces a possible jail term of six months. Under Italian law, the alleged crime carries a penalty of up to three years in open court but convictions are normally lower in the case of the fast-track proceedings for which Google has opted, which are closed to the press and public.

All four deny negligence, saying they could not have prevented the incident and stressing that the company took prompt action to identify the four perpetrators, who were expelled as a result. The video was pulled as soon it was drawn to Google's attention, their lawyers said.

In asking for the penalties, Milan prosecutors Alfredo Robledo and Francesco Cajani argued that Google should have been able to prevent the cameraphone video being posted.

The search engine should not have left itself open to incidents which allegedly "trampled fundamental rights," they told the court. The unidentified teenager who filed suit against the Google executives withdrew it in February.

Lawyers for the boy did not say why he had retracted the suit but he is thought to have reached an out-of-court settlement. Despite the boy's action the trial continued because Milan city hall and the Italian Down's association Vividown are standing as plaintiffs.

In the footage, posted on September 8, 2006 and removed on November 7, 2006, the boy was seen being taunted, insulted and kicked by one student in particular as others look on. The location appeared to be a classroom and the people visible appeared to be about 16 years of age.

The video was posted in Google Italy's 'Most Fun Videos' section and got 5,500 hits in its two months on the Web.

CASE 'SETS WORRYING PRECEDENT'. Google has expressed puzzlement over the case. When the suits were admitted it called the decision to take the case to trial ''difficult to understand'' and said it set a ''worrying precedent''. In a statement in June, Google added: "We will continue to vigorously defend our employees in this prosecution". ''As we have repeatedly made clear, our hearts go out to the victim and his family. ''We are pleased that as a result of our co-operation the bullies in the video have been identified and punished".

A lawyer for Milan city council on Wednesday asked for 300,000 euros in damages for alleged defamation of local schools Vividown said it was happy to let the trial judge, Oscar Magi, set a figure for possible damages.

The trial, which began in February, was adjourned until December 16, when defence lawyers will make their case. A verdict is expected some time in January, judicial sources said. Even if convicted, the four are in no danger of spending time in jail as all convictions under two years are suspended and there is automatic recourse to two levels of appeal. photo: a still from the video, shown on Italian TV in November 2006.