By pulling out of a landmark deal that allowed Ukrainian grain exports through the Black Sea, Russian President Vladimir Putin is taking a gamble that could badly damage Moscow’s relations with many of its partners that have stayed neutral or even been supportive of the Kremlin’s invasion of its neighbor.

Russia also has played the role of spoiler at the United Nations, vetoing a resolution on extending humanitarian aid deliveries through a key border crossing in northwestern Syria and backing a push by Mali’s military junta to expel U.N. peacekeepers—abrupt moves that reflect Moscow’s readiness to raise the stakes elsewhere.

Mr. Putin’s declared goal in halting the Black Sea Grain Initiative was to win relief from Western sanctions on Russia’s agricultural exports. His longer-term goal could be to erode Western resolve over Ukraine and get more concessions from the U.S. and its allies as the war grinds toward the 17-month mark.

The Kremlin doubled down on terminating the grain deal by attacking Ukrainian ports and declaring wide areas of the Black Sea unsafe for shipping.

But with the West showing little willingness to yield any ground, Mr. Putin’s actions not only threaten global food security but also could backfire against Russia’s own interests, potentially causing concern in China, straining Moscow’s relations with key partner Turkey and hurting its ties with African countries.

Turkish President Recep Tayyip Erdogan, who helped broker the grain deal with the UN a year ago, has pushed for its extension and said he would negotiate with Mr. Putin.

Turkey’s role as a top trading partner and a logistical hub for Russia’s foreign trade amid Western sanctions strengthens Mr. Erdogan’s hand and could allow him to squeeze concessions from Mr. Putin, whom he calls “my dear friend.”

Turkey’s trade with Russia nearly doubled last year to $68.2 billion, feeding U.S. suspicions that Moscow is using Ankara to bypass Western sanctions. Turkey says the increase is largely due to higher energy costs.

Their relationship is often characterized as transactional. Despite being on opposing sides in fighting in Syria, Libya and the decades-long conflict between Armenia and Azerbaijan, they have cooperated in areas like energy, defense, diplomacy, tourism and trade.

Ozgur Unluhisarcikli, director of the German Marshall Fund in Ankara, said the relationship’s dual nature dates back to the sultans and czars.

“Sometimes they compete, sometimes they cooperate. At other times they both compete and cooperate at the same time,” he said.

While the pendulum seems to have swung in Ankara’s favor for now, Mr. Unluhisarcikli noted the Kremlin has a few levers to pull, such as canceling a deferment of gas payments or removing financial capital for the Akkuyu nuclear plant being built by Russia. Moscow also could hurt Turkey by restricting Russian tourists, who visit in greater numbers than any other nationality. offering a steady flow of cash.

“How much weaker the relationship gets depends on how Russia responds to Turkey getting closer to the West,” he said.

Some observers in Moscow speculate that Russia agreed to extend the grain deal for two months in May to help Erdogan win reelection but was appalled to see his pro-Western shift afterward.

Mr. Erdogan backed Sweden’s membership in NATO earlier this month. In another snub to Moscow, Turkey allowed several Ukrainian commanders who led the defense of Mariupol last year to return home. They surrendered after a two-month Russian siege and then moved to Turkey under a deal that they stay there until the end of the war.

Kerim Has, a Moscow-based expert on Turkey-Russia ties, said Mr. Erdogan had been emboldened by his reelection to pursue rapprochement with the West, appointing a “pro-Western” Cabinet and adopting a stance that was causing “discomfort” in the Kremlin.

“It’s a dilemma for Putin,” Mr. Has said. “He supported Erdogan’s candidacy but he will face a more active, pro-Western Turkey under Erdogan in the coming period.”

Moscow could try to pressure Erdogan by challenging Turkey’s interests in northwestern Syria, where Ankara has backed armed opposition groups since the start of the conflict. Even though Russia has joined with Iran to shore up Syrian President Bashar Assad’s government while Turkey has backed its foes, Moscow and Ankara have negotiated cease-fire deals.

But Russia abruptly toughened its stand this month when it vetoed a UN Security Council resolution backed by virtually all members to continue humanitarian aid deliveries to opposition-held areas through the Bab el-Hawa border crossing with Turkey, a key lifeline for about 4.1 million people in the impoverished enclave. Moscow warned that if its rival draft was not accepted, the crossing would be shut.

The presence of 3.4 million Syrians in Turkey is a sensitive issue for Ankara. Mr. Erdogan has advocated their voluntary repatriation to parts of northern Syria under Turkish control.

Dareen Khalifa, senior analyst on Syria at the International Crisis Group, says Russia’s hardline approach to the issue was an attempt to pressure Ankara.

“Turkey will be directly impacted by that if the mechanism ends,” he said.

Others were skeptical Russia could use the border crossing issue to strong-arm Ankara. “I do not think Russia is in a position to increase its pressure on Turkey in Syria,” Mr. Has said.

Joseph Daher, a Swiss-Syrian researcher and professor at the European University Institute in Florence, Italy, observed that Russia could be trying to pressure the West by raising the prospect of a new wave of refugees in Europe.

Richard Gowan, UN director of the International Crisis Group, noted that along with the tougher stand on Syria, Russia’s “disruptive” actions included support for Mali’s push to expel U.N. peacekeepers.

“It looks like Russia is looking for ways to annoy the West through the UN,” he told The Associated Press.

Reflecting Moscow’s increasingly muscular stand, Russian military pilots recently have harassed U.S. aircraft over Syria in incidents that added to tensions between Moscow and Washington. The Pentagon described Russia’s maneuvers as unprofessional and unsafe, while Moscow sought to turn the tables by accusing the U.S. of violating deconfliction rules intended to prevent collisions over Syria.

Amid the hardball at the UN and in Syria, Russia has been courting African nations with promises of support.

The Kremlin has emphasized it stands ready to provide poor countries in Africa with free grain after the termination of the Black Sea deal, and Mr. Putin is set to woo African leaders at a summit in St. Petersburg later this month. Kremlin spokesman Dmitry Peskov said Moscow’s offer of free grain shipments would be on the agenda.

The Black Sea deal allowed Ukraine to ship 32.9 million metric tons of grain and other food to global markets. According to official data, 57 percent of the grain from Ukraine went to developing nations, while China received the most—nearly a quarter.

Ukrainian President Volodymyr Zelenskyy noted that 60,000 metric tons of grain destroyed by Russia’s strike on the port of Odesa on Wednesday were bound for China.

Mr. Putin, in turn, accused the West of using the grain deal to “shamelessly enrich itself” instead of its declared goal of easing hunger. Despite such rhetoric, the Russian move is not expected to play well in African countries.

Even as the Kremlin tried to contain the damage to those ties, it unleashed more attacks on Odesa and other ports to thwart Ukrainian attempts to continue grain shipments. Moscow described them as “strikes of retribution “for Monday’s attack that damaged the Kerch Bridge linking Moscow-annexed Crimea with Russia.

Hard-liners in Moscow praised Mr. Putin for halting the deal, which they have criticized as a reflection of what they described as the Kremlin’s futile hope to compromise with the West.

Pro-Kremlin commentator Sergei Markov lauded the retaliatory strikes and argued that the withdrawal from the deal was long overdue.

“The grain deal’s extension led to a drop in the government’s ratings and was fueling talk about betrayal on top,” he said.

This report contains information from The Associated Press.