The Fluorine-Containing α-Aminophosphonates as Agrochemical Agents

α-Aminophosphonates are structural analogues of amino acids in which the carboxylic acid functionality is replaced by a phosphonic acid group. These compounds exhibit a broad spectrum of biological activity and have found applications in agriculture and medicinal chemistry, particularly as bioactive agents in crop protection and enzyme inhibition. This study focuses on the synthesis of novel imidazole-containing α-aminophosphonates and the evaluation of their effects on seed germination and early plant growth under controlled laboratory conditions. A series of α-aminophosphonates was synthesized via a one-pot, three-component Kabachnik–Fields reaction using imidazole-substituted amines, ۲- and ۳-(trifluoromethyl)benzaldehydes, and dialkyl phosphites in benzene at ۸۰ °C. The reactants were combined in a molar ratio of amine:aldehyde:phosphite of ۱:۱.۲:۱.۲. A Dean–Stark apparatus was used to remove water produced during the reaction, and the mixture was heated and stirred for ۳۵ h. The isolated yields of the target compounds ranged from ۷۳ to ۸۱%. The α-aminophosphonates were characterized by IR, ۱H-NMR, and ۱۳C-NMR spectroscopy. For biological evaluation, the α-aminophosphonates were complexed with β-cyclodextrin (KhZR-۱۰۳-۱۰۵) as follows: each compound was dissolved in ethanol, mixed with β-cyclodextrin at a ۱:۱ molar ratio, and then dried at ۵۰ °C. For the growth assays, wheat seeds (Kazakhstan ۱۰) and soybean seeds (Zhansaya) were sterilized and soaked in aqueous solutions of the complexes (۵۰ mg/L) for ۶ h before incubation in Petri dishes under laboratory conditions. Biological tests showed that KhZR-۱۰۳ led to much better germination energy, laboratory germination, and germination intensity in wheat (Kazakhstan ۱۰) compared to the control and other treatments.

کلیدواژه ها:

Fluorine-containing &alpha ، -aminophosphonate ، Kabachnik&ndash ، Fields reaction ، &beta ، -Cyclodextrin complex ، plant growth-promoting activity