Dimethomorph (Ref: CME 151)

Dimethomorph (Ref: CME 151)	Last updated: 21/08/2024
(Also known as: dimethomorphe; AC 336379; CL 336379; BAS 550F)

SUMMARY

Dimethomorph is a systemic fungicide. It has a low aqueous solubility and a low volatility. It may be moderately persistent in both soil and water systems. Risks to biodiversity are generally in the moderate to low range. Dimethomorph has a low mammalian oral toxicity and is an irritant.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Moderately persistent; GUS: Transition state; Drainflow: Moderately mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate; Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide effective against various fungal pathogens in vines and other crops

Example pests controlled

Downy mildew; Anthracnose; Phytophthora cactorum, Septoria leaf spot; Late blight; Root rot; Crown rot

Example applications

Curcubits; Grapevines; Head lettuce; Onions; Potatoes; Fruit including blackberries, raspberries, strawberries, grapes

Efficacy & activity

Substance has been authorised and extensively used in the EU for > 10 years

Availability status

Current

Introduction & key dates

1988, first reported; 1993, first introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2027

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Netherlands/Germany

Date EC 1107/2009 inclusion expires

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
✓	✓	✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway
	✓

Additional information

Also used in

Australia, Iran, Morocco

Chemical structure

Isomerism

Isomeric - a mixture of two isomers (E & Z) but only the Z-isomer has fungicidal activity

Chemical formula

C₂₁H₂₂ClNO₄

Canonical SMILES

COC1=C(C=C(C=C1)C(=CC(=O)N2CCOCC2)C3=CC=C(C=C3)Cl)OC

Isomeric SMILES

COC1=C(C=C(C=C1)/C(=C/C(=O)N2CCOCC2)/C3=CC=C(C=C3)Cl)OC

International Chemical Identifier key (InChIKey)

QNBTYORWCCMPQP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H22ClNO4/c1-25-19-8-5-16(13-20(19)26-2)18(15-3-6-17(22)7-4-15)14-21(24)23-9-11-27-12-10-23/h3-8,13-14H,9-12H2,1-2H3/b18-14-

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
dimethomorph	Unstated isomer

General status

Pesticide type

Fungicide

Substance groups

Morpholine fungicide

Minimum active substance purity

965 g kg⁻¹ (E/Z isomer ratio 44/56)

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with good protective activity. Cellulose synthesis inhibitor.

CAS RN

110488-70-5

EC number

404-200-2

CIPAC number

483

US EPA chemical code

268800

PubChem CID

5889665

CLP index number

613-102-00-0

Molecular mass

387.86

PIN (Preferred Identification Name)

(2EZ)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-(morpholin-4-yl)prop-2-en-1-one

IUPAC name

(EZ)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine

CAS name

4-(3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)morpholine

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

Colourless to grey crystalline powder

Formulations

Property

Value

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

BASF
FCC
Nufarm
BOC Sciences

Example products using this active

Invader
Paraat
Forum
Acrobat
Pilaraxanil
Cabrio duo

Formulation and application details

Often available as a dispersible concentrate formulation.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

28.95

Low

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

100400

Acetone

112

Hexane

39000

Methanol

49500

Toluene

Melting point (°C)

125.2

Boiling point (°C)

584.9

Degradation point (°C)

280

Flashpoint (°C)

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

4.79 X 10⁰²

Calculated

Log P

2.68

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.2

Dissociation constant pKa) at 25 °C

-1.3

Calculated, Very strong acid

Vapour pressure at 20 °C (mPa)

9.7 X 10^-04

Low volatility

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

2.5 X 10^-05

Z-isomer

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

24 hr

From soil surface

Negligible

24 hr

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

200nm = 45000, 205nm = 30000, 221nm = 16000, 242nm = 20000, 286nm = 9100, 312nm = 4500

Surface tension (mN m⁻¹)

60.8

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

72.7

Moderately persistent

DT₅₀ (lab at 20 °C)

72.7

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

551

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2017 dossier lab studies DT₅₀ (normalised) range 17.8-599.1days, DT₉₀ range 159->1000 days, Soils=7; 2006 Dossier field studies DT₅₀ range 34-54 days; Other sources: DT₅₀ 92 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.9

Note

Published literature RL₅₀ range 2.1-14.8 days, 5 field & undercover grown crops, various matrices, n=7

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Seasonal variation: DT₅₀ 28 days summer, 86-107 days spring

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

Value

Moderately persistent

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Moderately fast

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

6.07

Moderately mobile

K_foc (mL g⁻¹)

419.4

¹/_n

0.86

Notes and range

EU 2017 dossier K_f range 2.09-19.7 mL g⁻¹, K_foc range 290-566 mL g⁻¹, ¹/_n range 0.814-0921, Soils=11

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.26

Calculated

Transition state

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

Value

1.10 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

3.6

Calculated using the Atkinson method. Assumed 0.5E+06 OH/cm³, 24 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-[3-(4-chlorophenyl)-3-3,4-dimethoxyphenyl)-1-oxo-2-propenyl-glycine

dimethomorph metabolite CUR 7117

Animal

4-[(E)-and(Z)-beta-(p-chlorophenyl)-3-hydroxy-4-methoxycinnamoyl]morpholine

dimethomorph metabolite Z67

Plant; Animal

4-[(E)-and(Z)-beta-(p-chlorophenyl)-4-hydroxy-3-methoxycinnamoyl]morpholine

dimethomorph metabolite Z69

Plant; Animal

4-chloro-3’,4’-dimethoxy-benzophenone

dimethomorph metabolite Z7

Plant

4-[3-(4-chlorophenyl)-3-3,4-dimethoxy-phenyl)-1-oxo-2-propenyl]-2-oxo-morpholine

dimethomorph metabolite Z37

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

3900

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 728.3 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

60.4

Colinus virginianus NOAEL

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

60.0

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 53.3 mg product/kg soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 2970

dicots & monocots
Vegetative vigour, ER₅₀
as g ha⁻¹

> 2970

dicots & monocots
Seedling emergence ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 102

Apis mellifera

Low

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

> 32.4

Apis mellifera

Moderate

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

2733

Apis mellifera

Bumblebees (Bombus spp.)

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

> 300

Bombus terrestris NOEC

Low

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

> 283.2

Bombus terrestris NOEC

Low

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 bee species (1)

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

Mode of exposure

Other bee species (2)

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

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as Mortality LR₅₀ g ha⁻¹

> 1360

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 6000

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 2210

Typhlodromus pyri

Beneficial insects (Ground beetles) as Mortality LR₅₀ g ha⁻¹

400

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

6.1

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.056

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

11.22

Danio rerio EC₅₀ Embryo

Moderate

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

> 20.1

Daphnia magna

Moderate

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

0.22

Daphnia magna

Moderate

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

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

12.0

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)

4.11

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

1.0

Lemna gibba

Moderate

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

29.2

Scenedesmus subspicatus

Low

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

9.8

Unknown species

Low

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

3900

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.2

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.05

Dog SF=100

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

0.6

Rat SF=100

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

0.6

Rat SF=100

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

0.15

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapid and extensive elimination via faeces (80%). At low doses biliary excretion is prominant.

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

May cause acute lung injury if inhaled
Possible liver & prostate toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H411

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions. Limited shelf-life. Store at 2-8 DegC

TRANSLATIONS

Language

Name

English

dimethomorph

French

dimethomorphe

German

Dimethomorph

Danish

dimethomorph

Italian

dimetomorf

Spanish

dimetomorf

Greek

Polish

dimetomorf

Swedish

dimetomorf

Hungarian

dimetomorf

Dutch

dimethomorf

Norwegian

dimetomorf

Record last updated:	21/08/2024
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