The Permian-Triassic transition.
Earth's largest extinction killed 57% of all families and 83% of all genera (53% of marine families, 84% of marine genera, about 96% of all marine species and an estimated 70% of land species) including insects. The evidence of plants is less clear, but new taxa became dominant after the extinction. The "Great Dying" had enormous evolutionary significance: on land, it ended the primacy of mammal-like reptiles. The recovery of vertebrates took 30 million years, but the vacant niches created the opportunity for archosaurs to become ascendant. In the seas, the percentage of animals that were sessile dropped from 67% to 50%. The whole late Permian was a difficult time for at least marine life, even before the "Great Dying".