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

The US government imposed around 600 new sanctions against Russia and its war machine. This is the largest single round of sanctions since Russia’s invasion of Ukraine on February 24, 2022.

The EU, for its part, imposed sanctions on several foreign companies over allegations that they exported dual-use goods to Russia that could be used in the war against Ukraine. The 27-nation bloc also targeted numerous Russian officials, including judicial officials, 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 were a response to Russian President Vladimir Putin’s “brutal war of conquest” and to Navalny’s death, adding: “We in the United States will continue to ensure that Putin pays a price for his aggression abroad and “Pays his oppression at home.”

But while previous sanctions have increased the cost of Russia’s fighting ability in Ukraine, they appear to have done little to deter Putin so far, and it was unclear whether the latest major round would significantly change that.

In a specific response to Navalny’s death, the State Department targeted three Russian officials the US said were linked to his death, including the deputy director of Russia’s Federal Penitentiary Service, who was promoted to colonel general by Putin on Monday, three days later Navalny has died.

The sanctions ban officials from entering the U.S. and block access to U.S. property. But they appear to be largely symbolic, as the officials are unlikely to travel to the West or have assets or family there.

White House national security spokesman John Kirby said further action would be expected later in connection with Navalny’s death, adding that “today is just a start.”

The Biden administration is imposing additional sanctions as House Republicans block billions of dollars in additional aid to Ukraine. The war is becoming increasingly entangled in the politics of the US election year. Former President Donald Trump expressed skepticism about the benefits of the NATO alliance, saying he would “encourage” Russia to “do whatever the hell they want” with countries he said were “doomed.” In my opinion, they do not take a position in the alliance.

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

“Russia is seizing Ukrainian territory for the first time in many months,” Biden said. “But here in America, the Speaker has given the House a two-week vacation. They must come back and get this done because the failure to support Ukraine at 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 statement said they also discussed developments in the Middle East.

Many of the new U.S. sanctions announced Friday target Russian companies that contribute to the Kremlin’s war effort – such as manufacturers of drones and industrial chemicals and importers of machine tools – as well as financial institutions such as the state-owned operator of the Russian payment system Mir.

The US will also impose visa restrictions on Russian authorities allegedly involved in the abduction and detention of Ukrainian children. In addition, 26 third-country nationals and companies from across China, Serbia, the United Arab Emirates and Liechtenstein are under sanctions for helping Russia evade existing fines.

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 aid to Ukraine. U.S. sanctions were not immediately addressed.

In total, the U.S. Treasury and State Departments have targeted more than 4,000 officials, oligarchs, companies, banks and others subject to Russia-related sanctions since the start of the war. The EU’s asset freezes and travel bans represent the 13th package of measures imposed by the bloc against individuals and organizations it suspects of undermining Ukraine’s sovereignty and territorial integrity.

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

In total, 106 more officials and 88 “entities” – often companies, banks, government agencies or other organizations – were added to the bloc’s sanctions list, bringing the number of targets to over 2,000 people and entities, including Putin and his associates.

Companies that make electronic components that the EU believes could have both military and civilian uses were among 27 companies accused of “directly supporting Russia’s military-industrial complex in its war of aggression against Ukraine,” it said it in a statement.

These companies – some based in India, Sri Lanka, China, Serbia, Kazakhstan, Thailand and Turkey – are subject to stricter export restrictions.

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

The Group of Seven allies have also imposed a $60 per barrel price cap on Russian oil to reduce Russia’s revenue from fossil fuels.

Critics of sanctions, price caps and other measures intended to stop the Russian invasion say they are not moving quickly enough.

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

“One way or another, at some point they will have to deal with Russia’s oil revenues and think about an oil embargo,” Snegovaya said. “The oil price cap practically no longer works.”

Deputy Treasury Secretary Wally Adeyemo told reporters that the US and its allies would not lower the price cap. “Rather, we will take measures that increase the costs” of Russian oil production.

The Treasury Department says the current cap is working, and an agency analysis found that the Kremlin’s oil tax revenues were more than 40 percent lower in the first nine months of 2023 as a result.

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

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

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