Bennettitales

Bennettitales (also known as cycadeoids) is an extinct order of seed plants.Arens NC, Stromberg C, Thompson A. "Introduction to the Bennettitales". University of California Museum of Paleontology. 

They first appeared in the Permian period and became extinct in most places toward the end of the Cretaceous. Bennettitales are among the most common Mesozoic seed plants. They looked like shrubs or cycads. 

Although the leaves of the Bennettitales looked like that of cycads, they had more complex flower-like reproductive organs. So some of them were probably pollinated by insects.

Certainly Bennettitales were cone-bearing seed plants. However, their relationship to other seed plants is unclear.

 References 

Category:Plant taxonomy
Category:Extinct plants
Category:Gymnosperms
Category:Fossil plants