title: Formulation factors that can reduce the formation of the phytotoxic impurity, N,N'-dibutylurea, from benomyl.
abstract: Fungicide benomyl is easily decomposed to carbendazim (MBC) and butyl isocyanate (BIC) in formulation, BIC is further hydrolyzed to butylamine. The BIC also reacts with butylamine to form N,N'-dibutylurea (DBU), a phytotoxic compound. The purpose of this study was to investigate the effects of selected additives and the manufacturing method of benomyl water dispersible granules (WG) on reducing DBU content in benomyl formulations. The manufacturing methods studied were granulation by extrusion, fluid bed spray, and spray dry. For the extrusion method, each benomyl powder formulation was homogenized by kneading with 20% v/w of 95% ethanol instead of water. After granulation, the percentages of the active ingredient benomyl and its degradation product carbendazim in each formulation were determined. For the fluid bed spray method, two formulations of wettable powders were formed. The first sample was granulated using 5% Na(2)SO(4) as the binder solution; the second sample used 2% urea. Changes in the active ingredient content after granulation were determined for each sample. For the spray dry method, four basic formulations of 70% benomyl, 5% sodium dodecyl sulfate (SDS) and 10% or 20% sodium sulfate were prepared, to study the effects of HMTA, urea and dispersant on reducing DBU formation in formulation. The DBU content of each formulation was measured for the fresh samples and after 1 year of storage. The results showed that urea had a stabilizing effect on benomyl, and reduced DBU formation. BIC increased benomyl yield during manufacturing, which reduced DBU content in fresh samples but allowed a greater potential for future DBU formation since it did not stabilize the extra benomyl. HMTA was found to reduce DBU in both aqueous BIC and prepared formulations. The study discusses how each of the selected constituents affected DBU formation and how commercial formulations can be improved to reduce DBU formation. From this study, it is clear that a safer benomyl formulation can be developed.
authors.affiliation: Department of Agricultural Chemistry, National Taiwan University, Taipei 106, Taiwan.
authors.forename: Ming-Hsun
authors.initials: MH
authors.lastname: Ho
authors.forename: Kao-Yung
authors.initials: KY
authors.lastname: Lin
authors.forename: Yei-Shung
authors.initials: YS
authors.lastname: Wang
mesh_terms: D001542:Benomyl / Q000737:chemistry / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid; D005659:Fungicides, Industrial / Q000737:chemistry / Q000633:toxicity; D007700:Kinetics; D010944:Plants / Q000187:drug effects*; D013501:Surface-Active Agents / Q000737:chemistry; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D017155:Wettability
chemical_list: D005659:Fungicides, Industrial; D013501:Surface-Active Agents; D014508:Urea; C483182:N,N'-dibutylurea; D001542:Benomyl