Turpentine Derived Secondary Amines for Sustainable Crop Protection: Synthesis, Activity Evaluation and QSAR Study

Abstract

In this study, we will report on the synthesis and application of efficient botanical agrochemicals from turpentine for sustainable crop protection. Two series of turpentine derived secondary amines were synthesized and identified by FT-IR, ¹H NMR, ¹³C NMR, and HRMS. The herbicidal activities against <i>Echinochloa crus-galli</i> were evaluated. The potential toxicity of the synthesized compounds was tested by MTT cytotoxicity analysis. The effect of structure of the synthesized secondary amines and corresponding Schiff base compounds on their activities was investigated by quantitative structure-activity relationship (QSAR) study. All target products were found to be low toxicity, with similar or higher herbicidal activities than commercial herbicides diuron and Glyphosate. Results of QSAR study showed that a best four-descriptor QSAR model with <i>R</i>² of 0.880 and <i>R</i>_loo² of 0.818 was obtained. The four descriptors most relevant to the herbicidal activities are <i>the min valency of a N atom</i>, <i>the max total interaction for a C-H bond</i>, <i>the relative number of aromatic bonds</i>, and <i>the min partial charge (Q</i>_<i>min</i><i>)</i>.