Ino Yamanaka

The flower shop maiden was an easy choice. Not only was she the Director of Konoha's Intelligence, but she also processes a technique which allows her to control others. Not to mention, she spent a lot of time at her flower shop which gave Kawaki relatively easy access to her. Her son, Inojin and her husband, Sai were also not home too often. Making her a relatively easy target if he could quickly subdue her.

Although most other ninja would probably focus more on Ino than anyone else in the village due to her attractive proportions and beautiful face, Kawaki didn't think too much of her. She was a means to an end, although potential offspring he could seed her with could have huge potential in his subjugated empire. She could also help his desire to rebel from Kara and take control of the Otsutsuki's power instead of being taken control by it.

So his plan was put into effect.... all he had to do was execute it.