Preparation and Applications of Flusulfamide Fungicide
Hillebrand S, et al. Modern Crop Protection Compounds, 2019, 2, 911-932.
Flusulfamide is a rather polar compound, but, due to its high melting point, its water solubility is relatively low. The compound is stable in water. Flusulfamide can be prepared by the reaction of 2-chloro-4-nitro- phenylaniline with 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride.
Applications of Flusulfamide
· Flusulfamide has been developed to control diseases caused by soil-borne pathogens from the order Plasmodiophorales (the only order of the plasmodiophorid group).
· Flusulfamide is used mainly as a soil treatment for the control of the causal agent of clubroot disease of Brassicae (crucifer) crops, Plasmodiophora brassicae.
· Furthermore, it has demonstrated efficacy against another member of the Plasmodiophorales in reducing the incidence of powdery scab on potatoes (Spongospora subterranea var. subterranea) in field trials, following soil treatment prior to planting or after spray treatment of the seed tubers (tuber dip).
· Although flusulfamide also shows antifungal activity on a cell test level against fungal plant pathogens, such as B. cinerea, Pythium aphanidermatum, and others, it has never been registered for use against these diseases.
Fluorine NMR Quantitative Analysis Method for Flusulfamide
Yamazaki T, et al. Journal of Chemical Metrology, 2017, 11(1), 16-22.
A new method for precise quantitative determination by 19F NMR spectroscopy can be used for the purity determination of fluorosulfonamide with an accuracy of less than 1% relative to reference values. A comparison of the areas of signals originating from 19F in different regions of a given molecule was carried out to optimize the measurement parameters. The parameters were then applied to the quantitative analysis of 19F in different compounds, such as flusulfamide and diflubenzuron.
· Flusulfamide, diflubenzuron, and chlorfenapyr are RMs. For the intermolecular analysis, chlorfenapyr was used as the internal standard (IS) to determine the purities of flusulfamide and diflubenzuron as analytes.
· The purity of flusulfamide and diflubenzuron was determined from chlorfenapyl (IS) by 19F NMR measurement under the optimum conditions. The results obtained were compared to the purity of the RMs.
· The excitation pulse offset was set midway between the IS signal and the analyte signal. The NMR spectra of mixtures of flusulfamide and chlorfenapyl, and diflubenzuron and chlorfenapyl are shown in Fig. 4 (a) and (b), respectively. In Fig. 4 (a), the signals of flusulfamide and IS were approximately 6.5 ppm apart, which is considered to be a small chemical shift difference.