WASHINGTON (AP) — The United States and European Union on Friday heaped hundreds of new sanctions on Russia in connection with the second anniversary of its invasion of Ukraine and in retaliation for the death of noted Kremlin critic Alexei Navalny last week in an Arctic penal colony.

The U.S. government imposed roughly 600 new sanctions on Russia and its war machine in the largest single round of penalties since Russia’s invasion of Ukraine on Feb. 24, 2022.

The EU, for its part, added sanctions on several foreign companies over allegations that they have exported dual-use goods to Russia that could be used in its war against Ukraine. The 27-nation bloc also targeted scores of Russian officials, including members of the judiciary, local politicians and people it said were “responsible for the illegal deportation and military re-education of Ukrainian children.”

President Joe Biden said the sanctions come in response to Russian President Vladimir Putin’s “brutal war of conquest” and to Navalny’s death, adding that “we in the United States are going to continue to ensure that Putin pays a price for his aggression abroad and repression at home.”

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But while previous sanctions have increased costs for Russia’s ability to fight in Ukraine, they appear to have done little so far to deter Putin and it was unclear that the latest big round would significantly alter that.

In specific response to Navalny’s death, the State Department targeted three Russian officials the U.S. says are connected to his death, including the deputy director of Russia’s Federal Penitentiary Service, who was promoted by Putin to the rank of colonel general on Monday, three days after Navalny died.

The sanctions bar the officials from traveling to the U.S. and block access to U.S.-owned property. But they appear largely symbolic given that the officials are unlikely to travel to or have assets or family in the West.

White House national security spokesman John Kirby said to “expect more” action later related to Navalny’s death, adding that “today this just a start.”

The Biden administration is levying additional sanctions as House Republicans are blocking billions of dollars in additional aid to Ukraine. The war is becoming entangled in U.S. election-year politics, with former President Donald Trump voicing skepticism about the benefits of the NATO alliance and saying that he would “encourage” Russia to “do whatever the hell they want” to countries that, in his view, are not pulling their weight in the alliance.

Biden on Friday called on Congress to pass Ukraine aid, which has stalled since House Speaker Mike Johnson blocked votes on aid passed by the Senate for Ukraine and other countries.

“Russia is taking Ukraine territory for the first time in many months,” Biden said. “But here in America, the speaker gave the house a two week vacation. They have to come back and get this done, because failure to support Ukraine in this critical moment will never be forgotten in history.”

Biden spoke later Friday with French President Emmanuel Macron about Russia’s recent actions and the need to support Ukraine. A White House readout said they also discussed developments in the Middle East.

Many of the new U.S. sanctions announced Friday target Russian firms that contribute to the Kremlin’s war effort — like drone and industrial chemical manufacturers and machine tool importers — as well as financial institutions, such as the state-owned operator of Russia’s Mir National Payment System.

The U.S. also will impose visa restrictions on Russian authorities it says are involved in the kidnapping and confinement of Ukrainian children. In addition, 26 third-country people and firms from across China, Serbia, the United Arab Emirates, and Liechtenstein are listed for sanctions, for assisting Russia in evading existing financial penalties.

The Russian foreign ministry called the EU sanctions “illegal” and said they undermine “the international legal prerogatives of the UN Security Council.” In response, the ministry is banning some EU citizens from entering the country because they have provided military assistance to Ukraine. It did not immediately address the U.S. sanctions.

Overall, since the start of the war, the U.S. Treasury and State departments have targeted more than 4,000 officials, oligarchs, firms, banks and others under Russia-related sanctions authorities. The EU asset freezes and travel bans constitute its 13th package of measures imposed by the bloc against people and organizations it suspects of undermining the sovereignty and territorial integrity of Ukraine.

“Today, we are further tightening the restrictive measures against Russia’s military and defense sector,” EU foreign policy chief Josep Borrell said. “We remain united in our determination to dent Russia’s war machine and help Ukraine win its legitimate fight for self-defense.”

In all, 106 more officials and 88 “entities” — often companies, banks, government agencies or other organizations — have been added to the bloc’s sanctions list, bringing the tally of those targeted to more than 2,000 people and entities, including Putin and his associates.

Companies making electronic components, which the EU believes could have military as well as civilian uses, were among 27 entities accused of “directly supporting Russia’s military and industrial complex in its war of aggression against Ukraine,” a statement said.

Those companies — some of them based in India, Sri Lanka, China, Serbia, Kazakhstan, Thailand and Turkey — face tougher export restrictions.

Some of the measures are aimed at depriving Russia of parts for pilotless drones, which are seen by military experts as key to the war.

A $60 per barrel price cap has also been imposed on Russian oil by Group of Seven allies, intended to reduce Russia’s revenues from fossil fuels.

Critics of the sanctions, price cap and other measures meant to stop Russia’s invasion say they are not working fast enough.

Maria Snegovaya, a senior fellow at the Center for Strategic and International Studies, said that primarily sanctioning Russia’s defense industry and failing to cut meaningfully into Russia’s energy revenues will not be enough to halt the war.

“One way or another, they will have to eventually address Russia’s oil revenues and have to consider an oil embargo,” Snegovaya said. “The oil price cap has effectively stopped working.”

Treasury Deputy Secretary Wally Adeyemo, in previewing the new sanctions, told reporters that the U.S. and its allies will not lower the price cap; “rather what we’ll be doing is taking actions that will increase the cost” of Russia’s production of oil.

The Treasury Department says the current cap is working, with an agency analysis finding that Kremlin oil tax revenue was more than 40 percent lower in the first nine months of 2023 because of it.

Adeyemo added that “sanctions alone are not enough to carry Ukraine to victory.”

“We owe the Ukrainian people who have held on for so long the support and resources they desperately need to defend their homeland and prove Putin wrong once and for all time.”

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Associated Press writers Josh Boak and Zeke Miller in Washington and Emma Burrows in London contributed to this report.