Clove bud oil: an efficient, economical and widely available oil for the inhibition of wheat seed germination

Pre-harvest sprouting refers to the precocious germination of the grain in the spike prior to harvest as a result of moist weather conditions at harvest time. From the agricultural viewpoint, it is necessary to impose an exogenous dormancy to wheat seeds in order to improve the resistance of seed to pre-harvest sprouting. In this regard, we found that clove bud essential oil is a strong inhibitor for wheat seed germination. The extract obtained from clove bud by supercritical fluid extraction using CO₂ as solvent minimized the number of extracts to two compounds, eugenol and eugenyl acetate. Eugenol, as the main constituent of the oil, was responsible for its strong inhibitory activity in wheat seeds. The aqueous solution of clove bud oil was submitted to germination assay at various concentrations from 50 to 400 mg/L. Complete inhibition of seed germination was recorded when the concentration was 400 mg/L. Roots and sprouts have similar sensitivity to inhibitory effect. In an empirical study, the synergistic cooperation of eugenol and eugenyl acetate from clove bud oil in the inhibition of seed germination was found to be a 1:1 ratio. The clove bud essential oil is widely available and will broaden the horizon of applications for natural and safe inhibitors in the fields.     

Green synthesis of 1,3-dihydrobenzimidazol-2-ones from aromatic diamines by microwave in a tetrabutylammonium bromide–ethanol molten salt paste

Environmental Chemistry Letters - The replacement of hazardous solvents by greener alternatives is a major goal in green chemistry. Benzimidazol-2-ones are heterocycles exhibiting a wide range of...     

Silica-supported antimony(III) chloride as a mild and reusable catalyst for the Paal–Knorr pyrrole synthesis

Heterogeneous catalysts are used for control of environmental pollution. Heterogeneous catalysts are easily separated from the reaction mixture, thus allowing their recovery and re-use. There is a need for catalysts that are efficient under mild conditions. Here, we show that silica-supported antimony(III) chloride (SbCl₃/SiO₂) acts as a highly efficient heterogeneous Lewis acid catalyst for the Paal–Knorr pyrrole synthesis at room temperature. We found that condensation of hexane-2,5-dione with aromatic and aliphatic primary amines in hexane using SbCl₃/SiO₂ with 7.6 wt% SbCl₃ was the best reaction condition. The silica support facilitated the workup of the reaction mixture and provided a reusable catalyst at least for 7 runs without significant loss in activity. Indeed, the yield was 98% for the first run and 84% for the 7th run. We conclude that low catalyst loading, operational simplicity, practicability and applicability to various substrates make this reaction an interesting alternative to previously applied procedures. From the environmental standpoint, this eco-friendly catalyst is stable, highly active, easy to prepare and handle.     

Vitamin B1 as a metal-free organocatalyst for greener Paal–Knorr pyrrole synthesis

This investigation discloses a greener reaction to prepare pyrrole derivatives. Metal-free catalysts are greener alternatives to existing metal catalysts in synthetic organic chemistry. Indeed, transition metals are often costly and toxic. They may be found as traces in health reaction products such as pharmaceuticals. Alternatively small organic molecules termed “organocatalysts” allow the synthesis of valuable products without traces of toxic metals. Here, we show for the first time the use of vitamin B₁ as new organocatalyst for the Paal–Knorr pyrrole synthesis under ambient conditions. Reaction conditions were optimized for the reaction of hexane-2,5-dione with 4-methoxyaniline. Ethanol was the most effective solvent. The conversion was quantitative using vitamin B₁, by comparison with a low yield of 30?% without catalysis. The best conditions were performed in ethanol with 5?mol % of vitamin B₁ during 1?h. This reaction was tested using various aromatic amines. To conclude the use of vitamin B₁ for the Paal–Knorr pyrrole, cyclocondensation has mild reaction conditions, is simple to perform, and gives moderate to excellent yields. It is therefore a promising reaction for the preparation of various pyrrole derivatives.