Dinocap (Ref: ENT 24727)

Dinocap (Ref: ENT 24727)	Last updated: 15/03/2024
(Also known as: DPC; DNOPC; crotothane; meptyldinocap; dinocap 4; dinocap 6)

SUMMARY

Dinocap is a dinitrophenol fungicide which is not approved for use in the UK nor the EU. It has a low aqueous solubility but soluble in most organic solvents. It is not considered persistent in soil and is non-mobile. Based on its physico-chemical parameters, Dinocap is not expected to leach to groundwater. It is moderately toxic to mammals, earthworms and bees but considered highly toxic to fish and aquatic invertebrates. Limited data is available on its toxicity to humans but some reports suggest it is a possible reproduction/developmental toxin.

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: 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 protectant fungicide for powdery mildew control but also suppresses mites

Example pests controlled

Powdery mildew; Spidermites

Example applications

Fruit including apple, apricot, cherry, citrus, grape, peach, pear; Cucumbers; Pumpkins; Squash; Hops

Efficacy & activity

Availability status

Current

Introduction & key dates

cica 1991, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Chemical structure

Isomerism

A chiral molecule - the the most active is (RS)-2-(1-methylheptyl)-4,6-dinitrophenyl (2E)-2-butenoate (meptyldinocap)

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, Acaricide, Insecticide

Substance groups

Dinitrophenol insecticide; Dinitrophenol acaricide; Dinitrophenol fungicide

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier 2,6-dinitro-4-octylphenol and 2,4-dinitro-6-octylphenol at ~26g/Kg

Substance origin

Synthetic

Mode of action

Contact with protective and curative action. Respiration inhibitor. Uncoupler of oxidative phosphorylation via disruption of proton gradient.

CAS RN

39300-45-3

EC number

228-088-8/254-408-0

CIPAC number

US EPA chemical code

036001

PubChem CID

5284389

CLP index number

609-023-00-6

Molecular mass

364.18

PIN (Preferred Identification Name)

mixture of 2,4-dinitro-6-octanylphenyl (2E)-but-2-enoate and 2,6-dinitro-4-octanylphenyl (2E)-but-2-enoate in which “octanyl” is a mixture of octan-2-yl, octan-3-yl and octan-4-yl groups

IUPAC name

mixture of 2,4-dinitro-6-octylphenyl crotonates and 2,6-dinitro-4-octylphenyl crotonates in which “octyl” is a mixture of 1-methylheptyl, 1-ethylhexyl and 1-propylpentyl groups

CAS name

2(or 4)-isooctyl-4,6(or 2,6)-dinitrophenyl (2E)-2-butenoate

Other status information

Marine pollutant

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 known

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Typhlodromus pyri

Physical state

Dark reddish brown, oily liquid

Related substances & organisms

meptyldinocap

dinocap 4

dinocap 6

dinocap

Formulations

Property

Value

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

Landseer
Rohm & Haas

Example products using this active

Karathane liquid
Crotothane
Caprane
Ezenosan
Mildex
Isocothane

Formulation and application details

Supplied in a variety of formulations including emulsifiable concentrates, wettable powders and dusts

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.183

Low

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

22000

Methanol

9000

n-Heptane

250000

Xylene

250000

Ethyl acetate

Melting point (°C)

-25

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

(closed cup)

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

3.16 X 10⁰⁶

Calculated

Log P

6.5

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.14

Dissociation constant pKa) at 25 °C

12.7

Strong base

Vapour pressure at 20 °C (mPa)

0.0073

Low volatility

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

1.62 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

240nm = 16727, 310nm = 2155

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

5.2

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4-24 days, DT₉₀ range 14-113 days; Defra give DT₅₀ range 4.5-6.1 days; Other sources: DT₅₀ 5 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

5.8

Note

Mango, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

10.1

Note

Published literature RL₅₀ range 5.8-14.4 days, fruit from 2 undercover crops, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.2

Fast

Note

pH sensitive: DT₅₀ 0.68 days at pH 4, 0.2 days at pH 5

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

Value

Non-persistent

Note

pH and temperature sensitive: DT₅₀ 280 days at pH 4 and 20 °C, 73 days at pH 4 and 30 °C, 6.5 days at pH 9 and 20 °C, 1.7 days at pH 9 and 30 °C. Values mean of 2,4- and 2,6- isomers. 2,6- isomer hydrolyses quickest.

Water-sediment DT₅₀ (days)

8.4

Fast

Water phase only DT₅₀ (days)

3.5

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)

Non-mobile

K_oc (mL g⁻¹)

5500

Notes and range

Freundlich

K_f (mL g⁻¹)

633

Non-mobile

K_foc (mL g⁻¹)

58245

¹/_n

1.05

Notes and range

EU dossier kf range 52-3102 mL g⁻¹, K_foc range 2889-310200 mL g⁻¹, ¹/_n range 0.87-1.73, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.83

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

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)

0.8

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

0.220

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1212

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

18.2

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

22989 mg kg feed⁻¹

Colinus virginianus

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

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

Eisenia foetida corr

Moderate

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

4.06

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 2.1 kg ha⁻¹; 28 Day

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)

29.3

Apis mellifera

Moderate

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

6.4

Apis mellifera

Moderate

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

Chronic

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 0.49 kg ha⁻¹

100

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as % Mortality at dose 0.49 kg ha⁻¹

100

Typhlodromus pyri Protonymph

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.0053

Lepomis macrochirus

High

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

0.00179

Pimephales promelas

High

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

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

0.0042

Daphnia magna

High

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

0.00094

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)

0.240

Chironomus riparius

Moderate

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)

0.32

Scenedesmus subspicatus

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)

1212

Rat

Moderate

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.0

Rat 4 hr

Other Mammal toxicity endpoints

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

0.004

Dog SF=100

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

0.004

Dog 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)

0.003

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Moderately toxic
Chronic occupational exposure has been shown to lead to cataracts and sometimes glaucoma

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Hazard Class 9

CLP classification 2013

Health: H302, H315, H317, H332, H360D, H373
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

dinocap

French

dinocap

German

Dinocap

Danish

dinocap

Italian

dinocap

Spanish

dinocap

Greek

dinocap

Polish

dinokap

Swedish

Hungarian

dinikap

Dutch

dinocap

Norwegian

Record last updated:	15/03/2024
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