* Deal for $4.4 billion, including debt
* Deal gives Couche-Tard stores in southwestern U.S. states
* Couche-Tard shares touch record high of C$67.99 (Adds background; updates shares)
By Arathy S Nair and Anet Josline Pinto
Aug 22 (Reuters) - Canadian convenience store operator Alimentation Couche-Tard Inc said it would buy smaller U.S. rival CST Brands Inc in a deal valued at about $4.4 billion, including debt, to expand its footprint in southwestern United States.
Laval, Quebec-based Couche-Tard, which operates under Circle K brand globally and its namesake retail brand in Quebec, is one of Canada's most acquisitive companies and has been expanding globally through deals in Europe, Canada and the United States.
The deal, the company's biggest ever, would strengthen its position in both the "sun belt" and the east coast of North America, Couche-Tard Chief Executive Brian Hannasch said in a statement, referring to southern and southwestern U.S. states.
The all-cash $48.53 per share offer for CST represents a premium of 2.15 percent to the stock's close on Friday.
Excluding debt, the deal is valued at about $3.67 billion, according to Reuters calculations.
Toronto-listed shares of Couche-Tard rose as much as 9.4 percent to a record of C$67.99. CST Brands' shares were little changed at $47.58 in midday trading.
San Antonio, Texas-based CST is one of the largest publicly traded fuel retailers in North America and operated 1,352 convenience stores in the United States and Canada in 2015.
The company, spun off from Valero Energy Corp in 2013, also operates convenience stores and gas stations in Canada and controls the general partner of gas station company CrossAmerica Partners LP.
CST, which has been under pressure from activist investors JCP Investment Management and Engine Capital LP, said in March it would explore strategic alternatives. The company's shares had since gained 39 percent through Friday's close.
In another retail deal on Monday, Canadian food and drug retailer Loblaw Cos Ltd agreed to buy Canadian healthcare technology company QHR Corp to expand its healthcare business.
Couche-Tard is the largest independent convenience store operator in the United States by number of company-operated stores. It had more than 10,500 stores worldwide, as of April 24.
The company, which has made at least eight acquisitions since 2014, agreed in March to buy 279 Esso-branded fuel and convenience sites from Imperial Oil Ltd for about C$1.69 billion ($1.31 billion).
Couche-Tard also said on Monday it would sell some Canadian assets of CST to Parkland Fuel Corp for about $750 million, after the deal closes, which is expected in early 2017.
The assets include CST's self-service fueling stations, commercial and home energy business, and a number of company-operated stores to be determined following the Competition Bureau of Canada's review of the transaction.
Couche-Tard said it would fund the deal with available cash, existing credit facilities and a new term loan.
Morgan Stanley & Co LLC and National Bank Financial advised Couche-Tard. Faegre Baker Daniels LLP and Davies Ward Phillips & Vineberg provided legal counsel.
BofA Merrill Lynch and J.P. Morgan Chase served as financial advisers to CST, while Wachtell, Lipton, Rosen & Katz and Stikeman Elliott acted as legal advisers. ($1 = 1.29 Canadian dollars) (Reporting by Arathy S Nair and Anet Josline Pinto in Bengaluru; Editing by Sriraj Kalluvila and Sayantani Ghosh)