NEW YORK >> Four men associated with a Japan-based crime syndicate known as “yakuza” have been charged with trying to negotiate a deal to exchange high-powered weapons for drugs with an undercover U.S. agent, federal prosecutors announced Thursday.

The men were arrested earlier this week in Manhattan after a sting operation led by the Drug Enforcement Administration. Prosecutors said the DEA agent infiltrated the organization by posing as an arms dealer eager to trade surface-to-air missiles — presumably meant for warring factions in Myanmar — in exchange for methamphetamine and heroin destined for New York City.

“The expansive reach of transnational criminal networks like the Yakuza presents a serious threat to the safety and health of all communities,” DEA Administrator Anne Milgram said in a statement.

The defendants made initial appearances in federal court in Manhattan, where they were ordered held without bail, prosecutors said. A message was left with a lawyer for Takeshi Ebisawa, a Japanese national who was singled out as an alleged ringleader of the local crew.

Court papers describe the yakuza as an “international criminal network, which spans Japan, Thailand, Burma, Sri Lanka and the United States.”

The papers added that the defendants who were allegedly seeking the deal with the DEA undercover “understood the weapons to have been manufactured in the United States and taken from United States military bases in Afghanistan and planned for the narcotics to be distributed in the New York market.”