This work was aimed at developing a prototype system based on multispectral digital photogrammetry to support tests required by international regulations for new Plant Protection Products (PPPs). In particular, the goal was to provide a system addressing the challenges of a new PPP evaluation with a higher degree of objectivity with respect to the current one, which relies on expert evaluations. The system uses Digital Photogrammetry, which is applied to multispectral acquisitions and Artificial Intelligence (AI). The goal of this paper is also to simplify the present screening process, moving it towards more objective and quantitative scores about phytotoxicity. The implementation of an opportunely trained AI model for phytotoxicity prediction aims to convert ordinary human visual observations, which are presently provided with a discrete scale (forbidding a variance analysis), into a continuous variable. The technical design addresses the need for a reduced dataset for training the AI model and relating discrete observations, as usually performed, to some proxy variables derived from the photogrammetric multispectral 3D model. To achieve this task, an appropriate photogrammetric multispectral system was designed. The system operates in multi-nadiral-view mode over a bench within a greenhouse exploiting an active system for lighting providing uniform and diffuse illumination. The whole system is intended to reduce the environmental variability of acquisitions tending to a standard situation. The methodology combines advanced image processing, image radiometric calibration, and machine learning techniques to predict the General Phytotoxicity percentage index (PHYGEN), a crucial measure of phytotoxicity. Results show that the system can generate reliable estimates of PHYGEN, compliant with existing accuracy standards (even from previous PPPs symptom severity models), using limited training datasets. The proposed solution addressing this challenge is the adoption of the Logistic Function with LASSO model regularization that has been shown to overcome the limitations of a small sample size (typical of new PPP trials). Additionally, it provides the estimate of a numerical continuous index (a percentage), which makes it possible to tackle the objectivity problem related to human visual evaluation that is presently based on an ordinal discrete scale. In our opinion, the proposed prototype system could have significant potential in improving the screening process for new PPPs. In fact, it works specifically for new PPPs screening and, despite this, it has an accuracy consistent with the one ordinarily accepted for human visual approaches. Additionally, it provides a higher degree of objectivity and repeatability.