The influence of β-cyclodextrin-epichlorohydrin (β-CD-EP) polymers on the improvement of the solubility and antifungal activity of carbendazim has been investigated. Meanwhile, the potential of the chitosan and β-CD-EP composite film used as a plant healthcare material for carbendazim-controlled release to protect rape against Sclerotinia sclerotiorum (Lib.) de Bary has been evaluated. β-CD-EP-1 and 2 (β-CD content, 750 mg/g and 440 mg/g, respectively) were found to significantly improve the solubility of the guest molecule carbendazim (17.9 and 18.5 times, respectively) and the 1:1 stoichiometry of the host-guest was confirmed by the Job’s plot. A slight synergism was observed for the β-CD-EP/carbendazim complex against S. sclerotiorum (Lib.) de Bary, indicating an enhancement to the bioavailability of carbendazim. The in vitro release studies revealed that β-CD-EP polymers could efficiently modulate carbendazim release behaviors, such as the release retard and rate. The in vivo efficacy experiments demonstrated that the β-CD-EP/carbendazim and chitosan composite film could significantly prolong the effective duration of carbendazim at a concentration of 100 μg/mL compared with spraying carbendazim at 500 μg/mL. Thereby, a highly useful and strategic concept in plant disease control by a plant healthcare material—the chitosan and polymeric β-CD-EP composite film—is provided, which could also serve as a concept for related plant diseases.
The reaction of isodehydracetic acid with amines was serendipitously found to afford β-enaminones in the presence of the coupling agent 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC). Under the optimal reaction condition, 23 examples of α-aminomethylene glutaconic anhydride were obtained at approximately 30−80% yields. This is a concise, operationally simple method to expediently synthesize a new type of β-enaminone-containing compound.
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