fbpx
Wikipedia

Cyazofamid

January 01, 1970

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
Names
IUPAC name
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)imidazole-1-sulfonamide
Other names
IKF 916
Identifiers
  • 120116-88-3 Y
3D model (JSmol)
  • Interactive image
9064229
ChEBI
  • CHEBI:81841
ChEMBL
  • ChEMBL1863429
ChemSpider
  • 8037772
ECHA InfoCard 100.111.751
EC Number
  • 601-671-8
KEGG
  • C18573
  • 9862076
UNII
  • QJC4S2YQ4B
  • DTXSID9034492
  • 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:
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 most often sold under the brand name Ranman.[5]

Synthesis edit

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 edit

  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 edit

  • Ohshima, Takeshi; Komyoji, Terumasa; Mitani, Shigeru; Matsuo, Norifusa; Nakajima, Toshio (2004). "Development of a Novel Fungicide, Cyazofamid". Journal of Pesticide Science (in Japanese). 29 (2). Pesticide Science Society of Japan: 147–152. doi:10.1584/jpestics.29.147. eISSN 1349-0923. ISSN 1348-589X. S2CID 84909424. AGRIS id JP2004007452. CiNii NAID 130004444938. ISSN-L 0385-1559.
  • Anastassiadou, Maria; Arena, Maria; Auteri, Domenica; Brancato, Alba; Bura, Laszlo; Carrasco Cabrera, Luis; Chaideftou, Eugenia; Chiusolo, Arianna; Crivellente, Federica; De Lentdecker, Chloe; Egsmose, Mark; Fait, Gabriella; Greco, Luna; Ippolito, Alessio; Istace, Frederique; Jarrah, Samira; Kardassi, Dimitra; Leuschner, Renata; Lostia, Alfonso; Lythgo, Christopher; Magrans, Oriol; Mangas, Iris; Miron, Ileana; Molnar, Tunde; Padovani, Laura; Parra Morte, Juan Manuel; Pedersen, Ragnor; Reich, Hermine; Santos, Miguel; Sharp, Rachel; Sturma, Juergen; Szentes, Csaba; Terron, Andrea; Tiramani, Manuela; Vagenende, Benedicte; Villamar-Bouza, Laura (2020). "Updated peer review of the pesticide risk assessment of the active substance cyazofamid". EFSA Journal. 18 (9). European Food Safety Authority (Wiley): 1-25. doi:10.2903/j.efsa.2020.6232. ISSN 1831-4732. PMC 7507320. PMID 32994826.

External links edit

  • "Cyazofamid". PubChem. Retrieved 2021-05-17.
  • "Pesticides - Fact Sheet for Cyazofamid - US EPA" (PDF). US EPA.

January 01, 1970
cyazofamid, fungicide, that, highly, specific, controlling, oomycete, plant, pathogens, such, phytophthora, infestans, organism, which, causes, late, blight, potato, mode, action, thought, involve, binding, center, coenzyme, cytochrome, reductase, names, iupac. 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 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 3H3Key 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 C 13H 13Cl N 4O 2S 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 Cyazofamid is most often sold under the brand name Ranman 5 Contents 1 Synthesis 2 References 3 Further reading 4 External linksSynthesis editProcesses 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 nbsp References edit 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 Further reading editOhshima Takeshi Komyoji Terumasa Mitani Shigeru Matsuo Norifusa Nakajima Toshio 2004 Development of a Novel Fungicide Cyazofamid Journal of Pesticide Science in Japanese 29 2 Pesticide Science Society of Japan 147 152 doi 10 1584 jpestics 29 147 eISSN 1349 0923 ISSN 1348 589X S2CID 84909424 AGRIS id JP2004007452 CiNii NAID 130004444938 ISSN L 0385 1559 Anastassiadou Maria Arena Maria Auteri Domenica Brancato Alba Bura Laszlo Carrasco Cabrera Luis Chaideftou Eugenia Chiusolo Arianna Crivellente Federica De Lentdecker Chloe Egsmose Mark Fait Gabriella Greco Luna Ippolito Alessio Istace Frederique Jarrah Samira Kardassi Dimitra Leuschner Renata Lostia Alfonso Lythgo Christopher Magrans Oriol Mangas Iris Miron Ileana Molnar Tunde Padovani Laura Parra Morte Juan Manuel Pedersen Ragnor Reich Hermine Santos Miguel Sharp Rachel Sturma Juergen Szentes Csaba Terron Andrea Tiramani Manuela Vagenende Benedicte Villamar Bouza Laura 2020 Updated peer review of the pesticide risk assessment of the active substance cyazofamid EFSA Journal 18 9 European Food Safety Authority Wiley 1 25 doi 10 2903 j efsa 2020 6232 ISSN 1831 4732 PMC 7507320 PMID 32994826 External links edit Cyazofamid PubChem Retrieved 2021 05 17 Pesticides Fact Sheet for Cyazofamid US EPA PDF US EPA Retrieved from https en wikipedia org w index php title Cyazofamid amp oldid 1165966498, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.