Synthesis, characterization, and bioactivity of rosin quaternary ammonium salt derivatives

Abstract

Two series of rosin quaternary ammonium salts (QAS) were synthesized using the same path. The structure of the target products was characterized by HPLC, MS, IR, and 1HNMR, and the bioactivity was determined by filter paper method using Trametes versicolor (white-rot fungus) and Gloeophyllum trabeum (brown-rot fungus), which are two kinds of general wood decay fungi in nature. The results showed that all compounds tested had a satisfactory anti-fungal effect at the molarity of 0.025 mmol/mL. Hereinto, acrylpimaric Gemini QAS had better bioactivity than dehydrogenated or tetrahydrogenated rosin QAS against Trametes versicolor. To this fungus, quaternary ammonium groups, which wraps up the membrane of microorganism and disrupts the balance in cell membrane, plays the leading role for its bioactivity. To Gloeophyllum trabeum, the inhibition activity of acrylpimaric QAS and dehydrogenated rosin QAS are almost at the same level and larger than tetrahydrogenated rosin QAS, so we conclude that both quaternary ammonium group and aromatic group play important roles. Compared with dodecyl dimethyl benzyl ammonium chloride (1227), which is a commercially available quaternary ammonium salt type fungicide, acrylpimaric acid quaternary ammonium salts have approximate bioactivity against Gloeophyllum trabeum. In conclusion, rosin derivatives with functional groups would do well in wood preservative applications.