Cyazofamid

Cyazofamid
Names

IUPAC name 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)imidazole-1-sulfonamide
Other names IKF 916
Identifiers
CAS Number	120116-88-3^Y
3D model (JSmol)	Interactive image
Beilstein Reference	9064229
ChEBI	CHEBI:81841
ChEMBL	ChEMBL1863429
ChemSpider	8037772
ECHA InfoCard	100.111.751
EC Number	601-671-8
KEGG	C18573
PubChem CID	9862076
UNII	QJC4S2YQ4B
CompTox Dashboard (EPA)	DTXSID9034492
InChI InChI=1S/C13H13ClN4O2S/c1-9-4-6-10(7-5-9)12-13(14)16-11(8-15)18(12)21(19,20)17(2)3/h4-7H,1-3H3 Key: YXKMMRDKEKCERS-UHFFFAOYSA-N
SMILES CC1=CC=C(C=C1)C2=C(N=C(N2S(=O)(=O)N(C)C)C#N)Cl
Properties^[1]
Chemical formula	C₁₃H₁₃ClN₄O₂S
Molar mass	324.78 g·mol⁻¹
Density	1.45 g/cm³
Melting point	152.7 °C
Solubility in water	0.107 mg/L (20 °C)
log P	3.2
Hazards^[2]
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H410
Precautionary statements	P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Cyazofamid is a fungicide that is highly-specific in controlling oomycete plant pathogens such as Phytophthora infestans, the organism which causes late blight in potato. Its mode of action is thought to involve binding to the Q_i center of Coenzyme Q – cytochrome c reductase.^[3]^[4]

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.
^ PubChem Database. "Cyazofamid".
^ 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.
^ "Fungicides". ISKBC – ISK Biosciences CORPORATION. Retrieved 2021-05-25.
^ 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.
^ Ning, Bin-Ke; Xu, Cheng; Li, Zong-Ying; Wang, Yue-Mei; Sun, Qiao-Nan (2013). "CCDC 958848: Experimental Crystal Structure Determination". Cambridge Structural Database. Cambridge Crystallographic Data Centre. doi:10.5517/cc115rlk.