Dimoxystrobin (Ref: BAS 505F)

Dimoxystrobin (Ref: BAS 505F)	Last updated: 14/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A fungicide used for disease control in cereals and some other crops

Example pests controlled

Brown rust; Ear blight; Stem rot; Stem canker; Dark leaf and pod spot; Light leaf spot

Example applications

Wheat; Oilseed rape

Efficacy & activity

Availability status

Current

Introduction & key dates

2003

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/01/2021

EU Candidate for substitution (CfS)

Yes - low ADI / ARfD / AOEL; two 'Persistent-Bioaccumulative-Toxic' criteria; endocrine disrupting properties

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

Chemical structure

Isomerism

Isomeric, existing in the E- and Z-forms. The E-isomer is dominant and accounts for around 88-98% of dimoxystrobin,

Chemical formula

C₁₉H₂₂N₂O₃

Canonical SMILES

CC1=CC(=C(C=C1)C)OCC2=CC=CC=C2C(=NOC)C(=O)NC

Isomeric SMILES

CC1=CC(=C(C=C1)C)OCC2=CC=CC=C2/C(=N\OC)/C(=O)NC

International Chemical Identifier key (InChIKey)

WXUZAHCNPWONDH-DYTRJAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H22N2O3/c1-13-9-10-14(2)17(11-13)24-12-15-7-5-6-8-16(15)18(21-23-4)19(22)20-3/h5-11H,12H2,1-4H3,(H,20,22)/b21-18+/f/h20H

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Strobilurin

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Protectant, curative and translaminar. Respiration inhibitor (QoL fungicide).

CAS RN

149961-52-4

EC number

CIPAC number

739

US EPA chemical code

PubChem CID

10936292

Molecular mass

326.39

PIN (Preferred Identification Name)

(2E)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide

IUPAC name

(E)-2-(methoxyimino)-N-methyl-2-[a-(2,5-xylyloxy)-o-tolyl]acetamide

CAS name

(αE)-2-[(2,5-dimethylphenoxy)methyl]-α-(methoxyimino)-N-methylbenzeneacetamide

Other status information

PAN Listed as Highly Hazardous Chemical

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 crystalline solid

Related substances & organisms

epoxiconazole

Formulations

Property

Value

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

Swing-Gold
Pictor

Example products using this active

BASF

Formulation and application details

Often available as a suspension concentrate comprising of dimoxystrobin and other active substances.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

4.3

Low

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

72000

Acetone

22500

Toluene

22500

Methanol

37000

Ethyl acetate

Melting point (°C)

138.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

300

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.89 X 10⁰³

Calculated

Log P

3.59

High

Bulk density (g ml⁻¹)

1.24

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

6.00 X 10^-06

Low volatility

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

4.55 X 10^-08

Non-volatile

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

205nm = 3000, 254nm = 4800, 290nm = 290, No absorbance maximum >290nm

Surface tension (mN m⁻¹)

64.3

at 20°C 0.5%w/w

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

210

Persistent

DT₅₀ (lab at 20 °C)

210

Persistent

DT₅₀ (field)

22.9

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

365

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 88-262 days, field study DT₅₀ range 2-39 days, DT₉₀ ~1 year

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 4 to pH 9 over 30 days, up to 50 °C

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

15.3

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

9.6

Moderately mobile

K_foc

486

¹/_n

0.92

Notes and range

EU dossier kf range 0.58-18.62, K_foc range 195.8-935.3 mL g⁻¹, ¹/_n range 0.894-0.942, Soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.79

Calculated

Low leachability

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

Value

5.13 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(E-O-(2-hydroxycarbonyl-5-methyl)phenoxymethyl)-2-methoxyimino-N-methylphenyl acetamide

Soil

0.121

Major fraction, Relevant

(E-O-(5-hydroxycarbonyl-2-methyl)phenoxymethyl)-2-methoxyimino-N-methylphenyl acetamide

Soil

0.130

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(2E)-2-{2-[(5-carboxy-4-hydroxy-2-methylphenoxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide

505M76

Animal (Tissue, Milk)

(E)-2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methyl-acetamide

505M01

Soil (Photolysis)

(E)-O-(2,5-dimethyl-4-hydroxy phenoxymethyl)-2-methoxyimino-N-methylphenylacetamide

505M02

Animal (Tissue, Milk)

4-({2-[(1E)-N-methoxy-2-(methylamino)-2-oxoethanimidoyl] benzyl}oxy)-2,5-dimethylphenylglucopyranosiduronic acid

505M78

Animal (Liver, Fat)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

0.5

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

136

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1043 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Anas platyrhynchos NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0434

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.01

Oncorhynchus mykiss 28 day

Moderate

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

0.0394

Daphnia magna

High

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

0.0125

Daphnia magna

Moderate

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

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.01

Chironomus riparius

Moderate

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

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

Non-target plants

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

0.017

Pseudokirchneriella subcapitata

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)

> 79.4

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)

23.65

Eisenia foetida

Moderate

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

0.089

Eisenia foetida

High

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

30 / 30

Mortality / Reproduction [Dose: 0.2 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

30 / 30

Mortality / Reproduction [Dose: 0.2 kg ha⁻¹]
Typhlodromus pyri adult

Soil micro-organisms

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

Dose: 20 kg ha⁻¹ 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.005

Aquatic invertebrates Algae

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.3

Rat

Other Mammal toxicity endpoints

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

0.004

Mouse SF=1000

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

0.004

Rat SF=200

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

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

0.02

Rat 7 day SF=200

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=60.0 µg l⁻¹

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Harmful if inhaled

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Code is usually 9

CLP classification 2013

Health: H332, H351, H361d
Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R63
Xn - Harmful: R20
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S36/37, S46, S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

dimoxystrobin

French

dimoxystrobine

German

Dimoxystrobin

Danish

dimoxystrobin

Italian

dimoxystrobin

Spanish

dimoxistrobin

Greek

Polish

dimoksystrobina

Swedish

Hungarian

Dutch

Record last updated:	14/01/2021
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