Cyazofamid

Cyazofamid

File:Cyazofamid 200.svg
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 checkY
3D model (JSmol)	Interactive image
Beilstein Reference	9064229
ChEBI	CHEBI:81841
ChEMBL	ChEMBL1863429
ChemSpider	8037772
ECHA InfoCard
EC Number	601-671-8
E number
KEGG	C18573
PubChem CID	9862076
UNII	QJC4S2YQ4B
CompTox Dashboard (EPA)	{{#property:P3117}}
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
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
GHS labelling:
Pictograms	GHS09: Environmental hazard
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

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.

Cyazofamid is most often sold under the brand name Ranman.

Synthesis

Processes to manufacture cyazofamid were disclosed in patents from Ishihara Sangyo Kaisha, Ltd. 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.

Synthesis of the fungicide cyazofamid

Further reading

• AGRIS id JP2004007452. CiNii NAID 130004444938. ISSN-L 0385-1559.