1 Enoch 10:4

3 And now instruct him that he may escape and his seed may be preserved for all the generations of the world.' 4 And again the Lord said to Raphael: 'Bind Azâzêl hand and foot, and cast him into the darkness: and make an opening in the desert, which is in Dûdâêl, and cast him therein. 5 And place upon him rough and jagged rocks, and cover him with darkness, and let him abide there for ever, and cover his face that he may not see light. 6 And on the day of the great judgement he shall be cast into the fire. And heal the earth which the angels have corrupted, and proclaim the healing of the earth, that they may heal the plague, and that all the children of men may not perish through all the secret things that the Watchers have disclosed and have taught their sons. 8 And the whole earth has been corrupted through the works that were taught by Azâzêl: to him ascribe all sin.' 9 And to Gabriel said the Lord: 'Proceed against the bastards and the reprobates, and against the children of fornication: and destroy [the children of fornication and] the children of the Watchers from amongst men [and cause them to go forth]: send them one against the other that they may destroy each other in battle: for length of days shall they not have. 10 And no request that they (i.e. their fathers) make of thee shall be granted unto their fathers on their behalf; for they hope to live an eternal life, and that each one of them will live five hundred years.' 11 And the Lord said unto Michael: 'Go, bind Semjâzâ and his associates who have united themselves with women so as to have defiled themselves with them in all their uncleanness.

Date: 200-50 B.C.E.
* Dates are based on scholarly estimates

Clement of Alexandria Fragments 2:4

Woe unto them! he says, for they have gone in the way of Cain. For so also we lie under Adam's sin through similarity of sin. Clouds, he says, without water; who do not possess in themselves the divine and fruitful word. Wherefore, he says, men of this kind are carried about both by winds and violent blasts. Trees, he says, of autumn, without fruit,— unbelievers, that is, who bear no fruit of fidelity. Twice dead, he says: once, namely, when they sinned by transgressing, and a second time when delivered up to punishment, according to the predestined judgments of God; inasmuch as it is to be reckoned death, even when each one does not immediately deserve the inheritance. Waves, he says, of a raging sea. By these words he signifies the life of the Gentiles, whose end is abominable ambition. Wandering stars,— that is, he means those who err and are apostates are of that kind of stars which fell from the seats of the angels— to whom, for their apostasy, the blackness of darkness is reserved forever. Enoch also, the seventh from Adam, he says, prophesied of these. In these words he verities the prophecy.

Date: 195-205 C.E.
* Dates are based on scholarly estimates