The fall and punishment of the Watchers
Raphael was commanded to bind Azazel hand and foot, and to cast him into the a hole in the desert (Duda’el) that the Lord had made. Raphael threw rugged and sharp rocks and covered Azazel’s face so that he would not see light. Michael was commanded to bound Semyaza and his associates in the valleys of the earth. They will remain there until the day of judgment when he will be cast into the fire.
1 Enoch 85-90 gives a similar account of the fall of the angels. In these passages, a star, Azazel, fell from heaven and began to pasture among the oxen (mankind). A number of stars then fell and were transformed into bulls. They began to cover the cows (the angels married mortal women), who then gave birth to elephants, camels, and asses (the giants). The oxen then became restless and began to fight, but they became prey to the wild beasts.
The archangels then appear in the disguise of men. One seizes the first of the fallen stars and casts it into the abyss. A second gives the elephants, camels, and asses a sword so that they will slay each other. A third archangel stones the other fallen stars and casts them into the gulf. The story then goes on to describe the Maccabean revolt, which leads to a description of the final struggle between good and evil.
The Book of Jubilees tells an account of the fall of the angels similar to that of 1 Enoch. It explains that the Watchers originally descended to the earth to teach mankind and do what is just, but they ‘inned with the daughters of men because these had begun to mix with earthly women so that they became defiled.’ (Jubilees 4:22) God was displeased with the angels because of their lust for the daughters of men
“Malalael “named [his son] Jared because during his lifetime the angels of the Lord who were called Watchers descended to earth to teach mankind and to do what is just and upright upon the earth” Jubilees 4:15
In Jubilees, Mastema is the chief of the spirits. As God commanded the angels to bind all the evil spirits, Mastema came and asked the Lord that some of the spirits might be allowed to remain with him to do his will. God granted his request and allowed one tenth of the spirits to remain with Mastema, while the other nine parts would be condemned.
“When Mastema, the leader of the spirits, came, he said: ‘Lord creator, leave some of them before me; let them listen to me and do everything that I tell them, because if none of them is left for me I shall not be able to exercise the authority of my will on mankind. For they are meant for (the purposes of) destroying and misleading before my punishment because the evil of mankind is great.’ Then he said that a tenth of them should be left before him, while he would make nine parts descend to the place of judgment.” – Jubilees 10:8-9