<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3874</id>
  <title>T3D3819</title>
  <common-name>Cymoxanil</common-name>
  <description>Cymoxanil is a solid compound with the formula C7H10N4O3 and an average molecular weight of 198.18 g/mol. Cymoxanil belongs to the oximes, a subclass of organonitrogen compounds within the organic compounds. This exogenous fungicide is used as both a curative and preventative foliar fungicide and operates as a local systemic. It penetrates rapidly into the plant, which prevents it from being washed off by rain, and it controls diseases during the incubation period to prevent crop damage. The compound is primarily active against fungi in the Peronosporales order, including Peronospora, Phytophthora, and Plasmopara. In Europe, it is sold for use on sugarbeets, tomatoes, potatoes, grapes, hops, and other vegetable crops, though it is not currently registered in the U.S. Cymoxanil is characterized by low chronic and acute toxicity.

The compound is found in or released from six recorded sources: drinking water and water supply, agriculture and land management (pesticides), food, food processing and cookware (preparation of malt), and building and construction (tents or canopies, ladders, and floors). Recorded exposure routes include touch, oral, and inhalation. There are five recorded protein targets for cymoxanil: urokinase-type plasminogen activator (PLAU), C-C motif chemokine 2 (CCL2), urokinase plasminogen activator surface receptor (PLAUR), sulfotransferase 2A1 (SULT2A1), and one other protein.</description>
  <cas>57966-95-7</cas>
  <pubchem-id>5364079</pubchem-id>
  <chemical-formula>C7H10N4O3</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)</mechanism-of-toxicity>
  <metabolism>Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is a man-made compound that is used as a pesticide.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2013-04-25T07:56:50Z</created-at>
  <updated-at type="dateTime">2026-03-31T17:32:49Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C18498</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCNC(=O)NC(=O)C(=N\OC)\C#N</moldb-smiles>
  <moldb-formula>C7H10N4O3</moldb-formula>
  <moldb-inchi>InChI=1S/C7H10N4O3/c1-3-9-7(13)10-6(12)5(4-8)11-14-2/h3H2,1-2H3,(H2,9,10,12,13)/b11-5+</moldb-inchi>
  <moldb-inchikey>XERJKGMBORTKEO-VZUCSPMQSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">198.1793</moldb-average-mass>
  <moldb-mono-mass type="decimal">198.075290206</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL59983</chembl-id>
  <chemspider-id>4516330</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002780</chemdb-id>
  <dsstox-id>DTXSID6032358</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00009143</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>103.58000000000001</moldb-polar-surface-area>
  <moldb-refractivity>46.778000000000006</moldb-refractivity>
  <moldb-polarizability>18.780844772228857</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>5</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>7.385165972186631</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.5566052266416834</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-0.16</moldb-alogps-logp>
  <moldb-alogps-logs>-1.87</moldb-alogps-logs>
  <moldb-alogps-solubility>2.68e+00 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic nitrogen compounds</superklass>
  <klass>Organonitrogen compounds</klass>
  <subklass>Oximes</subklass>
  <paper-count type="integer">354</paper-count>
  <sync-id>CED0012527</sync-id>
  <structure-inchikey>XERJKGMBORTKEO-VZUCSPMQSA-N</structure-inchikey>
  <structure-fingerprint>800000000000000000000000000004008000008000000000000002000000000000000000000000000000000100000000000000000000000000009000000000000000000000000020000020010100040004000000000000000300110000000040000000000000000000000000000000000000000000000000000040000000000000010000000080000000000000200800000000000000000000000000000000000000008000000002000000000000000000000000000000000000000000000000008000000000000000000000000200000000000000000000000000000000000000000000000440000000000000000400000000000000</structure-fingerprint>
  <structure-pattern-fingerprint>2000000102060000000000010820000000000000050000002400600200000c4000005000800000000021000080000004600002808c10010200443000b0000084110000000000000080100000e20000000000004000003200000420000009800c2000000044020000000000d0100000200080100d014004313c02000010000a004000180440000808000200080800081004000a444010020000080000800000004310000008400000000900042c201082c0000000010800000201000000020001000004040000000080000400010300000000000000400000000000080000000000080000200004010000004000200800000010004000100000008050010006</structure-pattern-fingerprint>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:56Z</structure-indexed-at>
</compound>
