Spanish police say they have intercepted the sale of nine military transport helicopters to Iran.
Five Spaniards and three Iranians were arrested after raids on industrial warehouses near Madrid and Barcelona.
It is illegal to export combat aircraft to Iran which is subject to a UN arms embargo and sanctions.
Police said the total value of the Bell helicopters, spares and other military materiel seized was around 100 million euros.
The group was also suspected of preparing to sell spare parts for combat helicopters to Venezuela without export licences.
Spain’s Interior Minister Alfredo Perez Rubalcaba said the helicopters has been purchased in Israel.