Synthesis and study of substituted 1-((1,3-dioxolan-4-yl)methyl)-1H-1,2,4-triazoles as plant growth regulators

¹ Moscow Institute of Physics and Technology, 141701, Dolgoprudny, Moscow Region, Russian Federation
² Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russian Federation

¹ Corresponding author: talismanov@phystech.edu

Abstract

The search for new effective plant growth regulators characterized by low application rates, low toxicity, and rapid biodegradability in plant-based products, soil, and the environment has become increasingly important in light of the growing regulatory requirements for pesticides. The search for new plant growth stimulants among the well-studied 1,2,4-triazole and 1,3-dioxolane derivatives allows for the combination of the growth-regulating properties of both 1,2,4- triazole and 1,3-dioxolane in a single molecule. An effective two-step method for the synthesis of substituted 1-((1,3-dioxolan-4-yl)methyl)-1H- 1,2,4-triazoles has been developed for the purpose of testing their growth- regulating activity. Using azeotropic removal of water, this reaction produced intermediate 4-chloromethyl-1,3-dioxolanes in high yields and with a high level of purity. In the second stage, the resulting 4-chloromethyl- 1,3-dioxolanes were alkylated with the sodium salt of 1,2,4-triazole by refluxing in dimethylformamide. The compounds were obtained in moderate yields and required purification by column chromatography and conversion to stable and easy-to-handle oxalate salts. The compounds were identified using NMR and IR spectroscopy. The synthesized compounds were tested for growth-regulating activity in vivo using agar medium on cucumber seedlings at concentrations ranging from 0.001 to 10 mg/L. Water was used as a reference standard. Tests were conducted over an 8-day period. The test results demonstrated significant retardant properties of the studied compounds when applied to the above-ground parts of plants, with the compounds stimulating the accumulation of both wet and dry biomass at a range of concentrations. The conducted studies demonstrated the potential of searching for new retardants in the 1-((1,3-dioxolan-4-yl)methyl)-1H- 1,2,4-triazole series.