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Prince Demande (anime)
Leader of the Black Moon Clan
Saphir (younger brother)
Prince Demande lead the Black Moon Clan to destroy Crystal Tokyo in the 30th Century. Eventually, he shifted his attention to conquer the past, specifically 20th Century Tokyo.
Sailor Moon R
Demande first sent Rubeus into the past, but Rubeus was defeated by the Sailor Senshi, and destroyed along with his ship. Esmeraude was then sent into the past, but the Sailor Senshi kept foiling her plans. Esmeraude was in love with Prince Demande. After her death, Demande's younger brother Saphir found out that Wiseman was only using them for his own twisted goals, and attempted to warn him, but was killed by Wiseman.
Shortly after, Demande attempted to hypnotize Sailor Moon so he could rule the universe with her by his side as his queen, and was about to kiss her, but Tuxedo Mask comes and rescues her.
Later he hypnotizes Sailor Moon again and nearly succeeds in winning her, but then she remembers her friends, Mamoru and escapes Demande's hypnotic powers. She was able to warn him about Wiseman's deception. Enraged, he turns on him up learning that he had killed Saphir in trying to warn him about the treachery. When Wiseman directed two dark energy blades at Sailor Moon, Demande jumped in front of her and took the hit, and died as a result of this injury. However, he was able to damage Wiseman, shattering his arms, but Wiseman came back together. Before his death Demande was able to tell Sailor Moon his true feelings for her - he did love her as a person.
His dark moon symbol becomes a third eye, which is able to stun and control his victims. He is also able to fire powerful energy blasts from his hands.