Dinocap (Ref: ENT 24727)

Dinocap (Ref: ENT 24727)	Last updated: 16/02/2021
(Also known as: DPC; DNOPC; crotothane; meptyldinocap; dinocap 4; dinocap 6)

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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

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)

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

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

Substance group

Dinitrophenol

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

131-72-6

Alternative/old 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

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not known

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Typhlodromus pyri

Physical state

Dark reddish brown, oily liquid

Related substances & organisms

meptyldinocap

dinocap 4

dinocap 6

Formulations

Property

Value

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

Karathane liquid
Crotothane
Caprane
Ezenosan
Mildex
Isocothane

Example products using this active

Landseer
Rohm & Haas

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

Bulk 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

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 on plant matrix

Value

5.8

Note

Mango, n=1

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

5500

Notes and range

Freundlich

K_f

633

Non-mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2,4-dinitro-6-octylphenol

Soil

0.220

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

992

Whole fish

Threshold for concern

CT₅₀ (days)

0.8

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0053

Lepomis macrochirus

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00179

Pimephales promelas

High

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

0.0042

Daphnia magna

High

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

0.00094

Daphnia magna

High

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)

Non-target plants

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

0.32

Scenedemus subspicatus

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)

29.3

Moderate

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

6.4

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)

Eisenia foetida corr

Moderate

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

4.06

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 0.49 kg ha⁻¹]
Aphidius rhopalosiphi adults

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 0.49 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 2.1 kg ha⁻¹; 28 days

Mesocosm study data

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)

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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 Code is usually 6.1

CLP classification 2013

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

EC Risk Classification

Reproduction risk category 2: R61
Xn - Harmful: R20/22, R48/22, R43
Xi - Irritant: R38
N - Dangerous for the environment: R50, R53

EC Safety Classification

S45, S53, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group I (great danger)

TRANSLATIONS

Language

Name

English

dinocap

French

dinocap

German

Dinocap

Danish

dinocap

Italian

dinocap

Spanish

dinocap

Greek

dinocap

Polish

dinokap

Swedish

Hungarian

dinikap

Dutch

dinocap

Record last updated:	16/02/2021
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