Cymoxanil (Ref: DPX T3217)

Cymoxanil (Ref: DPX T3217)	Last updated: 12/01/2021
(Also known as: cimoxanil)

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

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

Efficacy has been demonstrated from pilot studies and extensive global use.

Availability status

Current

Introduction & key dates

1976, first reported; mid 1970s first marketed

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Lithuania/Finland

Date EC 1107/2009 inclusion expires

31/08/2021

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓	✓	✓	✓	✓	✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
	✓	✓	✓	✓	✓	✓	✓	✓

Also used in

USA

Chemical structure

Isomerism

Exists as both E and Z isomers but the E-isomer is overwhelmingly favoured thermodynamically. Minimum E:Z ratio 99:1

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

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cymoxanil	-

General status

Pesticide type

Fungicide

Substance group

Cyanoacetamide oxime

Minimum active substance purity

970 g kg⁻¹

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

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)

Examples of recorded resistance

Physical state

White to pale pink crystals

Related substances & organisms

famoxadone

metalaxyl-M

mancozeb

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Besiege
Curzate
Matilda WG
Option
Tanos
Wakil XL
Cymoxanil 45WG

Example products using this active

Belchim
DuPont
Headland
Nufarm
Syngenta

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

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

780

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

28000

Ethyl acetate

62400

Acetone

5290

Toluene

n-Hexane

Melting point (°C)

160

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

156

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

4.68 X 10⁰⁰

Calculated

Log P

0.67

Low

Bulk density (g ml⁻¹)

1.31

Dissociation constant pKa) at 25 °C

9.3

Weak acid

Vapour pressure at 20 °C (mPa)

0.15

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.30 X 10^-05

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

244nm = 9333 & 9297

Surface tension (mN m⁻¹)

68.7

at 19°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.7

Non-persistent

DT₅₀ (lab at 20 °C)

1.4

Non-persistent

DT₅₀ (field)

3.5

Non-persistent

DT₉₀ (lab at 20 °C)

4.7

Non-persistent

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

Note

Potato tuber, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.7

Moderately fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

1.1

Non-persistent

Note

Stable at pH 4 and pH 5 at 20°C, DT₅₀ 0.02 days at pH 9 and 25 °C

Water-sediment DT₅₀ (days)

0.3

Fast

Water phase only DT₅₀ (days)

0.3

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

0.302

Mobile

K_foc

19.6

¹/_n

0.87

Notes and range

EU 2020 DAR dossier kf range 0.014-0.91, K_foc range 2.7-87.1 mL g⁻¹, ¹/_n range 0.77--0.96, Soils=11

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.47

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

3.24 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

0.700

Major fraction, Relevant

2-cyano-2-methoxyiminoacetic acid (Ref: IN-W3595)

Soil

0.181

Major fraction, Relevant

3-ethyl-4-(methoxyamino)-2,5-dioxoimidazolidine-4-carboxamide (Ref: IN-KQ960)

Soil

0.099

Minor fraction, Relevant

3-ethyl-4-(methoxyamino)-2,5-dioxoimidazolidine-4-carbonitrile (Ref: IN-JX915)

Soil

0.082

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

cyano(methoxyimino)acetic acid (Ref: IN-U3595)

ethylimidazolidinetrione-5-(o-methyloxime)

Soil (Aerobic)

{[(ethylamino)carbonyl]}ethylamino)carbonyl]amino}oxoacetic acid (Ref: IN-KP533)

1-ethyl-5-(methoxyimino)2,4-imidazolidin-2,4-dione (Ref: R3273)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

356

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

47.6

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

31.6

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 486

Anas platrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

14.9

Anas platyrhynchos NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.22

Oncorhynchus mykiss LOEC

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.067

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

44.4

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

Lemna gibba

Moderate

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.254

Anabaena flos-aquae

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 85.3

Apis mellifera

Moderate

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

6.6

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

480

>
Aphidius rhopalosiphi adult

% Effect

0 / 34

Mortality / Fecundity [Dose: 0.26 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

480

>
Typhlodromus pyri

% Effect

98.9 / 100

Mortality / Reproduction [Dose: 0.13 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 1.44 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

356

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.06

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.013

Dog SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.08

Rabbit SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.01

Dog SF=100

Dermal penetration studies (%)

1.0-75.0

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

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible testes, liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H302, H317, H361fd, H373
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22, R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S36/37, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

cymoxanil

French

cymoxanil

German

Cymoxanil

Danish

cymoxanil

Italian

cimoxanil

Spanish

cimoxanilo

Greek

Polish

cymoksanil

Swedish

cymoxanil

Hungarian

cymoxanil

Dutch

cymoxanil

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242