“Judah went against the Canaanites who lived in Hebron.” Specifically, Caleb of the tribe of Judah attacked the city of Hebron, but he would have had at least some other Judeans with him, and perhaps some warriors from other tribes as well (Josh. 14:6-15; 15:13-16). The verb can be read that Judah “had gone up.” This seems to be a description of what had happened in Joshua 15:14.
“Kiriath-arba, and they struck Sheshai and Ahiman and Talmai.” The reason that these three men, Sheshai and Ahiman and Talmai, are specifically mentioned is that they were Nephilim, part of the race of “fallen ones,” which means they were likely huge in stature and incredibly evil (Num. 13:33). Hebron was called “Kiriath-arba,” which means “the city of Arba,” and Arba was one of the Nephilim and the father of Anak (Josh. 21:11).
Sheshai, Ahiman, and Talmai were obviously very powerful and influential, because they are specifically mentioned three times in Scripture (Num. 13:22; Josh. 15:14, and Judg. 1:10). They were destroyed by Caleb and the Judean men who fought with him (Josh. 15:14, Judg. 1:10). Caleb was given Hebron as his personal inheritance because he had been faithful to Yahweh, especially because he and Joshua were the two faithful spies who Moses sent out from Kadesh-barnea to spy out the Promised Land (Num. 13:1-33).
“struck.” In this case, “struck” means “killed.”