Preparation and characterization of inclusion complex of iprodione and beta-cyclodextrin to improve fungicidal activity.
The effect of beta-cyclodextrin (beta-CD) on the improvement of the fungicidal activity of iprodione has been investigated. The inclusion complexation of beta-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 electron microscopy) and molecular simulation methods. The beta-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/beta-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 beta-CD as compared with the solubility of iprodione in deionized water in the absence of beta-CD. The bioassay demonstrated that the complex displayed over two-fold increase of the fungicidal activity. In addition, the possible structure of the beta-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.
Zhu
Xiao-Lei
XL
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Wang
Hong-Bo
HB
Chen
Qiong
Q
Yang
Wen-Chao
WC
Yang
Guang-Fu
GF
D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D004347:Drug Interactions; D005659:Fungicides, Industrial / Q000494:pharmacology*; D006827:Hydantoins / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D047392:beta-Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology*
D005659:Fungicides, Industrial; D006827:Hydantoins; D047392:beta-Cyclodextrins; D000620:Aminoimidazole Carboxamide; C031215:betadex; C033148:iprodione