Cyazofamid
{{Chembox
| ImageFile = Cyazofamid_200.svg
| IUPACName = 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)imidazole-1-sulfonamide
| OtherNames = IKF 916
|Section1={{Chembox Identifiers
| CASNo = 120116-88-3
| CASNo_Ref = {{Cascite|correct|CAS}}
| Beilstein = 9064229
| ChEBI = 81841
| ChEMBL = 1863429
| ChemSpiderID = 8037772
| EC_number = 601-671-8
| KEGG = C18573
| PubChem = 9862076
| UNII = QJC4S2YQ4B
| StdInChI=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
| StdInChIKey = YXKMMRDKEKCERS-UHFFFAOYSA-N
| SMILES = CC1=CC=C(C=C1)C2=C(N=C(N2S(=O)(=O)N(C)C)C#N)Cl
}}
|Section2={{Chembox Properties
|C=13|H=13|Cl=1|N=4|O=2|S=1
| Appearance=
| Density= 1.45 g/cm3
| MeltingPt= 152.7 °C
| BoilingPt=
| Solubility= 0.107 mg/L (20 °C)
| LogP=3.2
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|410}}
| PPhrases = {{P-phrases|273|391|501}}
}}
|Section8={{Chembox Related
}}
}}
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.{{cite journal |last1=Mitani |first1=Shigeru |last2=Araki |first2=Satoshi |last3=Takii |first3=Yasuko |last4=Ohshima |first4=Takeshi |last5=Matsuo |first5=Norifusa |last6=Miyoshi |first6=Hideto |title=The Biochemical Mode of Action of the Novel Selective Fungicide Cyazofamid: Specific Inhibition of Mitochondrial Complex III in Phythium spinosum |journal=Pesticide Biochemistry and Physiology |date=October 2001 |volume=71 |issue=2 |pages=107–115 |doi=10.1006/pest.2001.2569}}{{cite journal |last1=Mitani |first1=Shigeru |last2=Araki |first2=Satoshi |last3=Yamaguchi |first3=Tomona |last4=Takii |first4=Yasuko |last5=Ohshima |first5=Takeshi |last6=Matsuo |first6=Norifusa |title=Antifungal Activity of the Novel Fungicide Cyazofamid against Phytophthora infestans and Other Plant Pathogenic Fungi in Vitro |journal=Pesticide Biochemistry and Physiology |date=June 2001 |volume=70 |issue=2 |pages=92–99 |doi=10.1006/pest.2001.2541}}
Cyazofamid is most often sold under the brand name Ranman.{{cite web | title=Fungicides | website=ISKBC – ISK Biosciences CORPORATION | url=http://www.iskbc.com/products/fungicides/ | access-date=2021-05-25}}
Synthesis
Processes to manufacture cyazofamid were disclosed in patents from Ishihara Sangyo Kaisha, Ltd.{{cite patent |country=US |number=5869683 |status=patent |gdate=1999-02-09 |fdate=1997-11-03 |pridate=1994-09-08 |inventor =Jonishi H. et al. |title=Processes for producing 1-substituted-2-cyanoimidazole compounds |assign1=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.{{cite journal |doi=10.5517/cc115rlk |doi-access=free |year=2013 |last1=Ning |first1=Bin-Ke |last2=Xu |first2=Cheng |last3=Li |first3=Zong-Ying |last4=Wang |first4=Yue-Mei |last5=Sun |first5=Qiao-Nan |title=CCDC 958848: Experimental Crystal Structure Determination |publisher=Cambridge Crystallographic Data Centre |journal=Cambridge Structural Database}}
References
{{reflist}}
Further reading
- {{cite journal | last1=Ohshima | first1=Takeshi | last2=Komyoji | first2=Terumasa | last3=Mitani | first3=Shigeru | last4=Matsuo | first4=Norifusa | last5=Nakajima | first5=Toshio | title=Development of a Novel Fungicide, Cyazofamid | journal=Journal of Pesticide Science | publisher=Pesticide Science Society of Japan | volume=29 | issue=2 | year=2004 | issn=1348-589X | eissn=1349-0923 | doi=10.1584/jpestics.29.147 | pages=147–152 | s2cid=84909424 | language=ja| doi-access=free }} AGRIS id [http://agris.fao.org/agris-search/search.do?recordID=JP2004007452 JP2004007452]. CiNii NAID [http://ci.nii.ac.jp/naid/130004444938/ 130004444938]. ISSN-L [http://portal.issn.org/resource/ISSN-L/0385-1559 0385-1559].
- {{cite journal | last1=Anastassiadou | first1=Maria | last2=Arena | first2=Maria | last3=Auteri | first3=Domenica | last4=Brancato | first4=Alba | last5=Bura | first5=Laszlo | last6=Carrasco Cabrera | first6=Luis | last7=Chaideftou | first7=Eugenia | last8=Chiusolo | first8=Arianna | last9=Crivellente | first9=Federica | last10=De Lentdecker | first10=Chloe | last11=Egsmose | first11=Mark | last12=Fait | first12=Gabriella | last13=Greco | first13=Luna | last14=Ippolito | first14=Alessio | last15=Istace | first15=Frederique | last16=Jarrah | first16=Samira | last17=Kardassi | first17=Dimitra | last18=Leuschner | first18=Renata | last19=Lostia | first19=Alfonso | last20=Lythgo | first20=Christopher | last21=Magrans | first21=Oriol | last22=Mangas | first22=Iris | last23=Miron | first23=Ileana | last24=Molnar | first24=Tunde | last25=Padovani | first25=Laura | last26=Parra Morte | first26=Juan Manuel | last27=Pedersen | first27=Ragnor | last28=Reich | first28=Hermine | last29=Santos | first29=Miguel | last30=Sharp | first30=Rachel | last31=Sturma | first31=Juergen | last32=Szentes | first32=Csaba | last33=Terron | first33=Andrea | last34=Tiramani | first34=Manuela | last35=Vagenende | first35=Benedicte | last36=Villamar-Bouza | first36=Laura | title=Updated peer review of the pesticide risk assessment of the active substance cyazofamid | journal=EFSA Journal | publisher=European Food Safety Authority (Wiley) | volume=18 | issue=9 | year=2020 | issn=1831-4732 | doi=10.2903/j.efsa.2020.6232 | page=1-25| pmid=32994826 | pmc=7507320 | doi-access=free }}
External links
- {{cite web | title=Cyazofamid | website=PubChem | url=http://pubchem.ncbi.nlm.nih.gov/compound/9862076 | access-date=2021-05-17}}
- {{cite web|title=Pesticides - Fact Sheet for Cyazofamid - US EPA|website=US EPA|url=http://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-085651_01-Sep-04.pdf}}