| cymoxanil (Ref: DPX T3217) |
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Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
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 |
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Also used in: USA
Chemical structure:
| 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 |
General status:
| 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:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | None | |||
| Formulation and application details | Often supplied as wettable granules or powders that are mixed with water and applied as a spray or used as a seed treatment. | |||
ENVIRONMENTAL FATE
for cymoxanil
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 780 | A5 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 28000 | A5 - Ethyl acetate | - | |
| 65300 | A5 - Acetone | - | ||
| 5290 | A5 - Toluene | - | ||
| 37 | A5 - n-Hexane | - | ||
| Melting point (oC) | 161 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 156 | A3 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 4.68 X 1000 | Calculated | - |
| Log P | 0.67 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.31 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 9.3 | A5 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 20oC (mPa) | 0.15 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 3.80 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
0.34 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.15 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | 244nm = 9333 & 9297 | A5 | - | |
| Surface tension (mN m-1) | 68.7 | A5 at 19oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 0.7 |
K4 | Non-persistent |
| DT50 (lab at 20oC) | 1.4 | A5 | Non-persistent | |
| DT50 (field) | 3.5 | H4 | Non-persistent | |
| DT90 (lab at 20oC) | 4.7 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier Lab studies DT50 range 0.2-7.3 days, DT90 range 0.5-33.3 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 1.2 | R3 | - |
| Note | Potato tuber, n=1 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 1.7 | A5 | Moderately fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 1.1 | A5 | Non-persistent |
| Note | Stable at pH 4 and pH 5 @20deg C, DT50 0.02 days at pH 9 and 25 degC | |||
| Water-sediment DT50 (days) | 0.3 | A5 | Fast | |
| Water phase only DT50 (days) | 0.3 | A5 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 0.580 | A5 | Mobile |
| Kfoc | 43.6 | |||
| 1/n | 0.86 | |||
| Notes and range | EU dossier kf range 0.09-0.91, Kfoc range 15.1-87.1 mL/g, 1/n range 0.81-0.88, Soils=4 | |||
| pH sensitivity | No | |||
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) |
- | - | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | A5 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 760 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 47.6 | F4 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2945 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 29 | A5 Lepomis macrochirus | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.22 | F4 Oncorhynchus mykiss, LOEC | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 27 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.067 | F4 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 44.4 | F3 Americamysis bahia | Moderate | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | > 0.7 | A5 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.254 | A5 Anabaena flos-aquae | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 85.3 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 Eisenia foetida | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 6.6 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 480 | > A5 Aphidius rhopalosiphi, adult |
- |
| % Effect | 0 34 |
Mortality Fecundity Dose: 0.26 kg ha-1 A5 Aphidius rhopalosiphi, adult |
- | |
| Other arthropod (2) | LR50 g ha-1 | 480 | > A5 Typhlodromus pyri |
- |
| % Effect | 98.9 100 |
Mortality Reproduction Dose: 0.13 kg ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.44 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
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 Limits | - | - | - | |
| 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 | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | No further information available | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H302, H317, H361fd, H373 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R22, R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S36/37, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | Usually 3077 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| 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: Thursday 23 August 2018
Contact: aeru@herts.ac.uk