1 Enoch 7:2

Pseudepigrapha
1 And all the others them took wives for themselves, each choosing one for himself, and they began to unite with them and defiled themselves with them. They taught them sorcery, spells, and the art of extracting medicinal substances from plants. 2 The women became pregnant and gave birth to enormous giants, whose height was three thousand ells. 3 These giants consumed everything humans produced. And when humans could no longer support them, 4 the giants turned against them and devoured mankind. 5 They began to sin against birds, beasts, reptiles, and fish, eating each other’s flesh and drinking the blood. 6 Then the earth brought charges against these lawbreakers.
Date: 200-50 B.C.E. (based on scholarly estimates) Source

Tertullian Apology 22

Early Christian
In fact, they call upon Satan, the demon-chief, in their execrations, as though from some instinctive soul-knowledge of him. Plato also admits the existence of angels. The dealers in magic, no less, come forward as witnesses to the existence of both kinds of spirits. We are instructed, moreover, by our sacred books how from certain angels, who fell of their own free-will, there sprang a more wicked demon-brood, condemned of God along with the authors of their race, and that chief we have referred to. It will for the present be enough, however, that some account is given of their work. Their great business is the ruin of mankind.
Date: 197 C.E. (based on scholarly estimates) Source

Notes and References

"... Whether Justin drew directly from the Book of the Watchers is impossible to say with certainty, but it seems most likely that he was dependent upon something closely akin to the work we know by that name. The book’s early composition and widespread circulation from the second century bce on (as documented in Qumran manuscripts), its early translation into Greek, its use as an authoritative source in some of the earliest Christian writings (Jude, 1 Peter, 2 Peter), and Tertullian’s express dependence on “the Scripture of Enoch” for the same traditions (On the Apparel of Women 2-3; see also Apology 22; On Idolatry 4) make it the most likely conduit of the Watchers myth to Justin. Dependence on oral transmission and written materials now lost except as embedded in the extant Enochic works cannot be excluded, but neither should it be privileged over a well-documented literary channel, especially in view of the detail and specificity with which Justin’s presentation of the myth parallels that in the Book of the Watchers ..."

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