cymoxanil (Ref: DPX T3217) ** cimoxanil ** Translations

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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

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

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
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	famoxadone metalaxyl-M mancozeb

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Belchim DuPont Headland Nufarm Syngenta
Example products using this active	Besiege Curzate Matilda WG Option Tanos Wakil XL
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		1.28	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	2.94 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)	-	-	-	-

ECOTOXICOLOGY
for cymoxanil

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 (Apis spp.)	Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	> 100	A5 Apis mellifera	Low
	Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	> 85.3	A5 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	A5 Eisenia foetida	Low
Earthworms - Chronic NOEC, reproduction (mg kg-1)		6.6	A5 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	> 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 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 : 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
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
for cymoxanil

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

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Record last updated: Tuesday 03 March 2020
Contact: aeru@herts.ac.uk