Meptyldinocap (Ref: DE 126)

Meptyldinocap (Ref: DE 126)	Last updated: 18/07/2024
(Also known as: GF-1478)

SUMMARY

Meptyldinocap is a protectant, curative and eradicant fungicide. It has a low aqueous solubility, it is volatile and, based on its chemical properties, is unlikely to leach to groundwater. It is not persistent in soil and will usually degrade in water systems quickly. It is moderately toxic to mammals and bioaccumulation may be a concern. Whilst it is not highly toxic to birds, it is more toxic to many aquatic species including fish and algae.

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: Potential for particle bound transport: Medium	Ecotoxicity High alert: Birds chronic ecotoxicity: High; Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A dinitrophenol fungicide that is a single isomer of dinocap and active against powdery mildew mainly on fruit and other crops

Example pests controlled

Powdery mildew

Example applications

Vines; Curcubits; Fruit including apples, pears, peaches, plums, straberries, grapes,

Efficacy & activity

Availability status

Current

Introduction & key dates

2007, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2025

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/03/2025

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

Chile, Africa, India, Morocco

Chemical structure

Isomerism

Isomer of the existing active substance dinocap

Chemical formula

C₁₈H₂₄N₂O₆

Canonical SMILES

CCCCCCC(C)C1=CC(=CC(=C1OC(=O)C=CC)[N+](=O)[O-])[N+](=O)[O-]

Isomeric SMILES

CCCCCCC(C)C1=CC(=CC(=C1OC(=O)/C=C/C)[N+](=O)[O-])[N+](=O)[O-]

International Chemical Identifier key (InChIKey)

NIOPZPCMRQGZCE-WEVVVXLNSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H24N2O6/c1-3-5-6-7-8-9-11-14-12-15(19(22)23)13-16(20(24)25)18(14)26-17(21)10-4-2/h4,10,12-13H,3,5-9,11H2,1-2H3/b10-4+

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Dinitrophenol fungicide

Minimum active substance purity

900 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Protectant, curative and eradicant activity by inhibiting spore germination. Uncoupler of oxidative phosphorylation

CAS RN

131-72-6

Alternative/old CAS RN

6119-92-2

EC number

228-088-8

CIPAC number

811

US EPA chemical code

036000

PubChem CID

5284389

CLP index number

No data found

Molecular mass

364.39

PIN (Preferred Identification Name)

IUPAC name

(RS)-2-(1-methylheptyl)-4,6-dinitrophenyl crotonate

CAS name

2-(1-methylheptyl)-4,6-dinitrophenyl (2E)-2-butenoate

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

Yellowish brown liquid

Related substances & organisms

dinocap

dinocap 4

dinocap 6

Formulations

Property

Value

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

Dow AgroSciences
Landseer

Example products using this active

Kindred
karathane
GF-1478

Formulation and application details

Usually supplied as an emulsifiable concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.248

Low

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

252000

Acetone

256000

Ethyl acetate

251000

n-Heptane

256000

Xylene

Melting point (°C)

-22.5

Freezing point

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

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

3.55 X 10⁰⁶

Calculated

Log P

6.55

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.11

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.00792

Low volatility

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

1.16 X 10^-02

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral & Acidic solution: 240nm = 16727, 310nm = 2155
Basic solution: 260nm = 6575, 372nm = 12980, 405nm = 10969

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

12.0

Non-persistent

DT₅₀ (lab at 20 °C)

12.0

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

64.7

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4.1-22.4 days, DT₉₀ range 13.7-122 days; Manufacturers published lab studies range 4-24 days (E3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.8

Note

Mango fruit, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.4

Fast

Note

Natural light 40 deg N

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

Value

Moderately persistent

Note

pH sensitive: 447 days at pH4, 229 days at pH5, 56 and 30.4 days at pH7, 0.7 and 9.3 days at pH9, all at 20 °C

Water-sediment DT₅₀ (days)

3.54

Fast

Water phase only DT₅₀ (days)

5.7

Moderately fast

Sediment phase only DT₅₀ (days)

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)

705

Non-mobile

K_foc (mL g⁻¹)

958245

¹/_n

1.05

Notes and range

EU dossier K_f range 52-3102mL g⁻¹, K_foc range 2889-310200 mL g⁻¹, ¹/_n range 0.9-1.73, Soils=6; EU dossier and Manufacturers published data gives K_foc/K_oc range 2889-310200 mL g⁻¹

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-2.33

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

1.9

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

992

Whole fish

Threshold for concern

CT₅₀ (days)

0.6

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

2,4-dinitro-6-octylphenol

Major fraction

0.22

dinocap (Ref: ENT 24727)

Major fraction

0.832

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

2,4-dinitro-6-octylphenol

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2,4-diacetaminonitro-6-(1-methylpentanoate)phenol

Rat (Urine)

2-acetoamino-4-nitro-6-(1-methyl-alpha,beta-pentenoate)phenol

Rat (Urine)

2,4-dinitro-6-(1-methylpentanoate)phenol

Rat (Urine)

2,4-dinitro-6-(1-methylbutanoate)phenol

Rat (Urine)

2,4-dinitro-6-(1-methyl-beta-hydroxypentanoate)phenol

Rat (Urine)

2,4-dinitro-6-(1-methyl-alpha,beta-pentanoate)phenol

Rat (Urine)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

> 32.4

Rabbit Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Colinus virginianus for dinocap

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

344 mg kg bw⁻¹ day⁻¹

Colinus virginianus as dinocap

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

6.1

Colinus virginianus NOEL

High

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

302

Eisenia foetida corr

Moderate

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

Soil micro-organisms

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

Dose: 0.62 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

84.8

Moderate

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

Moderate

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

Chronic

Notes

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 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)

Beneficial insects (Parasitic wasps) as % Mortality at dose 0.84 kg ha⁻¹

16.7

Aphidius rhopalosiphi

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

10.91

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 490 g ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.0569

Lepomis macrochirus

High

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

0.00286

Pimephales promelas 34 day

High

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

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

0.0041

Daphnia pulicaria

High

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

0.00076

Daphnia magna

High

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

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)

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

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

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

2.12

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

> 2000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.24

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.016

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

0.12

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

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

0.008

Dermal penetration studies (%)

1.0-10.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable risks for proposed uses

Occupational

Acceptable risks for proposed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

EU MRL levels for some commodities subject to change in mid-2022

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver and thyroid toxicant

Handling issues

Property

Value and interpretation

General

Flammable
Not explosive or oxidising
IMDG Transport Hazard Class 9

CLP classification 2013

Handling: H226
Health: H302, H315, H317, H319, H332, H336, H360, H373
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

meptyldinocap

French

meptyldinocap

German

Meptyldinocap

Danish

meptyldinocap

Italian

meptyldinocap

Spanish

meptildinocap

Greek

Polish

meptyldinokap

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	18/07/2024
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