Preparation and Characterization of Inclusion Complex of Iprodione and β-Cyclodextrin to Improve Fungicidal Activity

• Published in: Journal of agricultural and food chemistry Vol. 55; no. 9; pp. 3535 - 3539
• Main Authors: Zhu, Xiao-Lei, Wang, Hong-Bo, Chen, Qiong, Yang, Wen-Chao, Yang, Guang-Fu
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 02.05.2007
• Subjects: Aminoimidazole Carboxamide - analogs & derivatives; Aminoimidazole Carboxamide - chemistry; Aminoimidazole Carboxamide - pharmacology; antifungal properties; beta-cyclodextrin; beta-Cyclodextrins - chemistry; beta-Cyclodextrins - pharmacology; Biological and medical sciences; chemical stability; cyclodextrins; Drug Interactions; Food industries; Fundamental and applied biological sciences. Psychology; Fungicides, Industrial - pharmacology; Hydantoins - chemistry; Hydantoins - pharmacology; inclusion complexes; iprodione; Models, Molecular; pesticide formulations; Physalospora; Physalospora piricola; Solubility; Spectrometry, Mass, Electrospray Ionization; Thanatephorus cucumeris; water solubility; Characterization; inclusion complex; Antifungal agent; Cyclodextrin; Inclusion; iprodione; molecular modeling; Preparation; Cyclodextrins; Modeling; antifungal activity
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf070197f

The effect of β-cyclodextrin (β-CD) on the improvement of the fungicidal activity of iprodione has been investigated. The inclusion complexation of β-CD with iprodione has been prepared and characterized by integrating some analytical techniques (such as electrospray ionization−mass spectrometry, differential scanning calorimetry, thermogravimetry, x-ray diffraction, and scanning eletron microscopy) and molecular simulation methods. The β-CD/iprodione inclusion complex has exhibited different spectroscopic features and properties from iprodione. The stoichiometric ratio and stability constant describing the extent of formation of inclusion complexes have been determined by phase solubility studies. The calculated apparent stability constant of the iprodione/β-CD complex was 407.5 M-1. The obtained inclusion complexes were found to significantly improve the water solubility of iprodione, and there is a 4.7-fold increase in the presence of 13 mM β-CD as compared with the solubility of iprodione in deionized water in the absence of β-CD. The bioassay demonstrated that the complex displayed over two-fold increase of the fungicidal activity. In addition, the possible structure of the β-CD/iprodione complex was proposed according to the results of the molecular dynamic simulation. The present study provided useful information for a more rational application of iprodione, diminishing the use of organic solvents and increasing its efficacy. Keywords: Cyclodextrins; iprodione; inclusion complex; antifungal activity; molecular modeling