cymoxanil (Ref: DPX T3217) |
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SUMMARY
Cymoxanil is a fungicide approevd for use in the EU and many other countries. It is highly soluble in water and considered quite volatile. It has a low potential for leaching to groundwater, is non persistent in soil and water systems. Cymoxanil is moderately toxic to mammals, may cause adverse effects on reproduction/development and has a high potential to bio-concentrate. It is moderately toxic to most aquatic organisms, earthworms and honeybees but less so to birds. GENERAL INFORMATION
for cymoxanil
Description: A fungicide used to control pathogens on a range of crops including potatoes and other crops.
Example pests controlled: Foliar late blight; Downy mildew; Powdery mildew
Example applications: Potatoes; Tomatoes; Grapes; Hops; Sugarbeet; Vines
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1976, first reported; mid 1970s first marketed
EC Regulation 1107/2009 (repealing 91/414):
Status | Approved |
Dossier rapporteur/co-rapporteur | Lithuania/Finland |
Date inclusion expires | 31/08/2021 |
EU Candidate for substitution (CfS) | No |
Listed in EU database | Yes |
Approved for use () or known to be used (
) in the following European countries:
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
Also used in: USA
Isomerism | Exists as both E and Z isomers but the E-isomer is overwhelmingly favoured thermodynamically |
Chemical formula | C7H10N4O3 |
Canonical SMILES | CCNC(=O)NC(=O)C(=NOC)C#N |
Isomeric SMILES | CCNC(=O)NC(=O)/C(=N/OC)/C#N |
International Chemical Identifier key (InChIKey) | XERJKGMBORTKEO-UHFFFAOYSA-N |
International Chemical Identifier (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+ |
2D structure diagram/image available? | Yes |
Pesticide type | Fungicide | |
Substance group | Cyanoacetamide oxime | |
Minimum active substance purity | 970 g/kg | |
Known relevant impurities | EU dossier - None declared | |
Substance origin | Synthetic | |
Mode of action | Foliar with protective and curative activity. | |
CAS RN | 57966-95-7 | |
EC number | 261-043-0 | |
CIPAC number | 419 | |
US EPA chemical code | 129106 | |
PubChem CID | 5364079 | |
Molecular mass (g mol-1) | 198.18 | |
PIN (Preferred Identification Name) | (2E)-2-cyano-N-(ethylcarbamoyl)-2-(methoxyimino)acetamide | |
IUPAC name | 1-[(EZ)-2-cyano-2-methoxyiminoacetyl]-3-ethylurea | |
CAS name | 2-cyano-N-((ethylamino)carbonyl)-2-(methoxyimino)acetamide | |
Other status information | - | |
Relevant Environmental Water Quality Standards | - | |
Herbicide Resistance Classification (HRAC) | Not applicable | |
Herbicide Resistance Classification (WSSA) | Not applicable | |
Insecticide Resistance Classification (IRAC) | Not applicable | |
Fungicide Resistance Classification (FRAC) | 27 | |
Examples of recorded resistance | - | |
Physical state | White to pale pink crystals | |
Related substances & organisms |
Formulations:
ENVIRONMENTAL FATE
for cymoxanil
Key metabolites:
Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy ![]() |
|
1-ethyl 5,6-di-2,4(1H,3H)pyridenedione (Ref: IN-U3204) ![]() |
Soil | 0.247 | Major fraction, Relevant | |
2-cyano-2-methoxyiminoacetic acid (Ref: IN-W3595) ![]() |
Soil | 0.101 | Major fraction, Relevant | |
3-ethyl-4-(methoxyamino)-2,5-dioxoimidazolidine-4-carboxamide (Ref: IN-KQ960) | Soil | 0.063 | Minor fraction, Relevant | |
3-ethyl-4-(methoxyamino)-2,5-dioxoimidazolidine-4-carbonitrile (Ref: IN-JX915) | Soil | 0.076 | Minor fraction, Relevant |
Other known metabolites:
Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
ethylimidazolidinetrione-5-(o-methyloxime) | - | Soil (Aerobic) | - | - |
{[(ethylamino)carbonyl]}ethylamino)carbonyl]amino}oxoacetic acid (Ref: IN-KP533) |
- | - | - | - |
cyano(methoxyimino)acetic acid (Ref: IN-U3595) |
- | - | - | - |
1-ethyl-5-(methoxyimino)2,4-imidazolidin-2,4-dione (Ref: R3273) |
- | - | - | - |
HUMAN HEALTH AND PROTECTION
for cymoxanil
General:
Property ![]() |
Value | Source/Quality Score/Other Information ![]() |
Interpretation ![]() |
|
Threshold of Toxicological Concern (Cramer Class) ![]() |
High (class III) | - | - | |
Mammals - Acute oral LD50 (mg kg-1) | 760 | A5 Rat | Moderate | |
Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
Mammals - Inhalation LC50 (mg l-1) | > 5.6 | A5 Rat, 4 hr (nose only) | - | |
Other Mammal toxicity endpoints | - | - | ||
ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.013 | A5 Dog, SF=100 | - | |
ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.08 | A5 Rabbit, SF=100 | - | |
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.01 | A5 Dog, SF=100 | - | |
Dermal penetration studies (%) | 1.0-75.0 | A5 concentration dependent | - | |
Dangerous Substances Directive 76/464 | - | - | - | |
Exposure Routes | Public | Acceptable risk to bystanders for intended uses | ||
Occupational | Acceptable risk to operators wearing protective clothing | |||
European MRLs | Click here for the EU MRL pesticide database | |||
Drinking Water Standards | - | - | - | |
Drinking Water MAC (μg l-1) | 0.1 | EU Dir 89/778/EC limit; A5 | - |
Health issues:
Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
A3; B3; C3; D0; E0 | - |
|||||||
Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
- |
|
|||||||
General human health issues | No further information available | |||||||
Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other![]() ![]() ![]() - : No data found |
Handling issues:
Language | Name |
English | cymoxanil |
French | cymoxanil |
German | Cymoxanil |
Danish | cymoxanil |
Italian | cimoxanil |
Spanish | cimoxanilo |
Greek | - |
Slovenian | cimoksanil |
Polish | cymoksanil |
Swedish | cymoxanil |
Hungarian | cymoxanil |
Dutch | cymoxanil |
Record last updated: Friday 08 November 2019
Contact: aeru@herts.ac.uk