Cyazofamid is most often sold under the brand name Ranman.[5]
Synthesis
Processes to manufacture cyazofamid were disclosed in patents from Ishihara Sangyo Kaisha, Ltd.[6] An acetophenone derivative was first treated with aqueous glyoxal and hydroxylamine to form an oxime-substituted imidazole ring system. This intermediate was treated with thionyl chloride and disulfur dichloride to convert the oxime to a cyano group and chlorinate the imidazole in the position next to the phenyl ring. Finally, treatment with dimethylsulfamoyl chloride gave cyazofamid, with the desired regiochemistry. This placed the sulfamoyl group on the nitrogen adjacent to the phenyl ring rather than the chlorine atom. The structure of the fungicide has been confirmed by X-ray crystallography.[7]
References
^Pesticide Properties Database. "Cyazofamid". University of Hertfordshire.
^Mitani, Shigeru; Araki, Satoshi; Takii, Yasuko; Ohshima, Takeshi; Matsuo, Norifusa; Miyoshi, Hideto (October 2001). "The Biochemical Mode of Action of the Novel Selective Fungicide Cyazofamid: Specific Inhibition of Mitochondrial Complex III in Phythium spinosum". Pesticide Biochemistry and Physiology. 71 (2): 107–115. doi:10.1006/pest.2001.2569.
^Mitani, Shigeru; Araki, Satoshi; Yamaguchi, Tomona; Takii, Yasuko; Ohshima, Takeshi; Matsuo, Norifusa (June 2001). "Antifungal Activity of the Novel Fungicide Cyazofamid against Phytophthora infestans and Other Plant Pathogenic Fungi in Vitro". Pesticide Biochemistry and Physiology. 70 (2): 92–99. doi:10.1006/pest.2001.2541.
^US patent 5869683, Jonishi H. et al., "Processes for producing 1-substituted-2-cyanoimidazole compounds", issued 1999-02-09, assigned to Ishihara Sangyo Kaisha Ltd.
