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Cyazofamid

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Cyazofamid
Names
IUPAC name
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)imidazole-1-sulfonamide
Other names
IKF 916
Identifiers
3D model (JSmol)
9064229
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.111.751 Edit this at Wikidata
EC Number
  • 601-671-8
KEGG
UNII
  • 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
  • CC1=CC=C(C=C1)C2=C(N=C(N2S(=O)(=O)N(C)C)C#N)Cl
Properties[1]
C13H13ClN4O2S
Molar mass 324.78 g·mol−1
Density 1.45 g/cm3
Melting point 152.7 °C
0.107 mg/L (20 °C)
log P 3.2
Hazards[2]
GHS labelling:
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 Qi center of Coenzyme Q – cytochrome c reductase.[3][4]

Cyazofamid is most often sold under the brand name Ranman.[5]

Synthesis

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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]

Synthesis of the fungicide cyazofamid

References

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  1. ^ Pesticide Properties Database. "Cyazofamid". University of Hertfordshire.
  2. ^ PubChem Database. "Cyazofamid".
  3. ^ 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.
  4. ^ 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.
  5. ^ "Fungicides". ISKBC – ISK Biosciences CORPORATION. Retrieved 2021-05-25.
  6. ^ 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. 
  7. ^ 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.

Further reading

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