As a new book reveals, the world of international diplomacy is full of bizarre pratfalls

Whether you are a diplomat, a prominent politician or a senior official at the United Nations, the image you like to present is of suave sophistication. Better that the rest of us do not know of the occasions when the best-laid plans, or best-written speeches, go abruptly awry.

Anecdotes from eras past of bloopers on the international affairs circuit are usually the quiet secret of aides and veteran interpreters who have toiled at state dinners or at the UN Security Council. But a few occasionally leak out. Whether entirely true or apocryphal, we rarely know – like the time that the famously unsmiling former Soviet Foreign Minister, Andrei Gromyko, allegedly eschewed the assistance of interpreters and attempted his own toast to an esteemed female counterpart at an official lunch, and instead of saying "bottoms up" blurted: "A toast to this gracious lady. Up your bottom."

The foibles of language have been at the root of many of the clangers. Some are funny, some have serious consequences. When Kofi Annan, the former UN secretary general, abruptly told the BBC in 2004 that the war in Iraq was "illegal", the US went ballistic (and the British, too, more quietly). To this day, it is not clear whether he really meant to say it, or merely erred from the tamer term he had always used up to that point, that it was "illegitimate". But once uttered, it was never retracted.

Misspeaking is not the only cause of embarrassment. At the UN it is sometimes a case of misplacing. Chuckling will eventually replace horror over the discovery of Iraqi nerve gas in a filing cabinet at the UN last Thursday. Neither UN inspectors nor US sleuths could find any weapons of mass destruction in Iraq after the 2003 invasion. No one thought to look in New York. What was not misplaced in 2004 was an elephant's penis – but more of that later.

Delve into Matthew Parris's Read My Lips, an anthology of political faux pas, and you will find this story, dating all the way back to 1948. At Christmastime, a Washington DC radio station contacted a handful of foreign ambassadors asking what they would most like for the festive season. Most understood the question correctly, like the French envoy who asked for "peace throughout the world" and his Soviet counterpart, who replied, "freedom for all people enslaved by imperialism". Poor old Sir Oliver Franks, the British ambassador, didn't quite get it, though. "Well, it's very kind of you to ask," he innocently responded. "I'd quite like a box of crystallised fruit."

A new trove of verbal blunders can be found in another book released in excerpts yesterday, this one written by the former Australian Foreign Minister, Richard Woolcott. Called Undiplomatic Activities, it offers a cornucopia of red-faced moments committed by him and his colleagues.

Consider Australia's envoy to France, who attempted national flattery when telling a distinguished audience that his career could be seen as having two parts: the part prior to his arrival in Paris, which was dull, and the fun part, which had begun thereafter. But his French was not up to it: instead, he revealed that "when I look at my backside, I find it is divided into two parts". Hilarity – and bemusement for the speaker – ensued. (What is it about diplomats and bottoms?)

Woolcott himself came mildly unstuck during a visit to the Indonesian city of Palembang, this time thanks to a none-too-skilled interpreter. What he said was innocuous: "Ladies and gentlemen, on behalf of my wife and myself, I want to say how delighted we are to be in Palembang." What came from the interpreter, less so. "Ladies and gentlemen, on top of my wife, I am delighted to be in Palembang."

Lost-in-translation gaffes are always best when sexual innuendo is inadvertently introduced. Woolcott also recalls how Bob Hawke hit the banana skin when he told an audience in Japan that he had not come "to play silly buggers" with them. That something would go horribly wrong with this phrase in the interpreters' booth was almost inevitable. After much consultation, this is what they said into the headsets of the Japanese dignitaries: "I am not here to play laughing homosexuals with you".

A leader of Australia's Labour Party, Kevin Rudd, made the same mistake as Gromyko, thinking he could do without interpreters on a visit to China. Rudd had studied Mandarin and thought he had the right words to express the closeness of the relationship between the two nations. Not quite. "Australia and China are enjoying simultaneous orgasms in their relationship," he told the audience.

Or there was the time when no translation was involved at all. An Asian minister was telling a long joke at a state banquet in South Korea. "The Korean interpreter was lost, but did not show it. He uttered a few sentences and the audience laughed and applauded," Mr Woolcott writes. After later being complimented on his translating skills, the interpreter confessed: "Frankly, minister, I did not understand your joke. So I said in Korean that the minister has told his obligatory joke – would you all please laugh heartily and applaud."

Back at the UN, one veteran correspondent recently recalled an occasion when Nikita Khrushchev lost his cool in the General Assembly when a minister from Indonesia was condemning totalitarianism. Khrushchev rushed to the podium and, according to the English interpreter, called the minister "a jerk" – enough to wake up the most somnambulant of delegates. It emerged, however, that the word used by the Soviet leader was a good deal ruder; what the original Russian slander was exactly, the discreet interpreter never did reveal.

Sleeping at the UN, meanwhile, is something every diplomat has done from time to time. The French government four years ago was not especially amused, however, when one of its elderly ambassadors, Alain Dejammet, found time to write a book containing his top 10 places to doze off inside UN headquarters. He recommended a variety of nooks and crannies in the labyrinthine building where peace and quiet were guaranteed, as well as a few especially snooze-inducing committees.

No one was sleeping, of course, when word leaked out on Thursday about the small bottle found in an old filing cabinet at UN offices in New York, three blocks from the Secretariat tower, that turned out to contain phosgene, a deadly chemical first used in the First World War and used by Saddam Hussein's regime to kill thousands of Kurds in the 1980s.

The container was uncovered as officials of Unmovic, the agency originally created to deploy inspectors to Iraq that was finally declared defunct by the Security Council just this June, were clearing out papers and other flotsam from their years of work. What Unmovic still has in its possession could fill a small, and rather interesting, museum: an engine from an Iraqi Scud missile, about 100 missile-guidance gyroscopes thrown into the Tigris river by Saddam's henchmen in 1996 and subsequently hauled out by UN divers, and countless other pieces of equipment, including chemical-agent detection machines.

It was one of these machines that was pressed into labour this week to determine whether any of the phosgene, held in suspension in oil in the container, had leaked into the air of the offices and, heaven forfend, throughout the whole building. It had not. Nonetheless, the UN came out very red-faced.

The chemical "find" reminded UN correspondents of another recent case of astonishing misplacement: the discovery in early 2004 of an aircraft "black box", again in a long-forgotten filing cabinet at the UN, that had come to New York from Rwanda at the time of the 1994 genocide. The flap was instantaneous. Le Monde suggested that it was the flight recorder from the Falcon aircraft that was carrying Rwanda's President Juvenal Habyarimana and Cyprian Ntayamirawere, his Burundian counterpart, when it was shot down by rebels – the event that triggered the massacres. "It sounds like a foul-up, a first-class foul-up," Annan told reporters after the discovery. Months later, it emerged that the black box was not connected to the Falcon.

Now retired, Annan probably still shudders over this and other such incidents during his eight years at the UN's helm. But surely not over the case of the big brass elephant.

In 1998, Annan was asked to preside over a familiar ritual at the UN: the unveiling of a gift from a member government. It was actually three governments this time – Kenya, Nepal and Namibia – and the present was a 3,000kg brass elephant, placed at the north-west corner of the lovely park adjacent to UN headquarters on the East River.

Its journey had been especially long. The artist had actually gone to the Kenyan bush, where he arranged for an elephant to be tranquillised long enough for him to take a cast. The completed cast was transported to a foundry in New York and, finally, after a project lasting 18 years, no less, the thing was put in place for the perusal of Annan and the rest of New York.

Unfortunately, it was not just its making that was long. So was its very remarkable male appendage. So alarmed was one aide to Annan that he sought to have the thing lopped off before the unveiling to avoid frightening children. The artist threatened to go public with the proposed mutilation; instead, gardeners were instructed to plant high bushes around the sculpture to screen the offending phallus – a job they are still doing today.

Whether the humour of the event was lost on Annan's speechwriter, nobody knows. "As we see this magnificent animal stand before us today, it was worth the wait," he declared. "The sheer size of this creature humbles us. And so it should. For it shows us that some things are bigger than we are." Indeed, they are.