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To follow the transdisciplinary ambition in much information science and philosophy leading to cognitive science we need to include a phenomenological and hermeneutical ground in order to encompass a theory of interpretative meaning and signification to achieve a transdisciplinary theory of knowing and communication. This is also true if we start in cybernetics and system theory that also have transdisciplinary aspirations for instance in Batesons ecological concept of information as a difference that makes a difference and in Luhmann’s triple autopoietic communication-based system theory. Charles Sanders Peirce’s pragmaticist semiotics integrates logic and information in interpretative semiotics. But although Peirce’s information theory is built on meaningful signs and he connects information to the growth of symbols, his information theory is empirically based in a realistic worldview, which in the development to modern biosemiotics include all living systems.