Plants emit an extraordinary diversity of chemicals that provide information about their identity and mediate their interactions with insects. However, most studies of this have focused on a few model species in controlled environments, limiting our capacity to understand plant-insect chemical communication in ecological communities. Here, by integrating information theory with ecological and evolutionary theories, we show that a stable information structure of plant volatile organic compounds (VOCs) can emerge from a conflicting information process between plants and herbivores. We corroborate this information " arms race" theory with field data recording plant-VOC associations and plant-herbivore interactions in a tropical dry forest. We reveal that plant VOC redundancy and herbivore specialization can be explained by a conflicting information transfer. Information-based communication approaches can increase our understanding of species interactions across trophic levels.