Dinobuton (Ref: OMS 1056)

Dinobuton (Ref: OMS 1056)	Last updated: 29/08/2024
(Also known as: ENT 27244; MC 1053; dinofen; UC 19786)

SUMMARY

Dinobuton is a dinitrophenol multi-use pesticide which is not approved for use in the UK nor the EU. It has a low aqueous solubility but soluble in most organic solvents. Limited information is available regarding its environmental fate but is reported as being non-mobile. It is moderately toxic to mammals, birds and bees but considered highly toxic to fish. Limited data is available on its toxicity to humans but some reports suggest it is a possible cardiovascular, liver and kidney toxicant

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 Low alert: Drainflow: Non-mobile Warning: Significant data are missing	Ecotoxicity High alert: Fish acute ecotoxicity: High Warning: Significant data are missing	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A dinitrophenol acaricide and fungicide used mainly on fruit and vegetables

Example pests controlled

Red spider mites; Powdery mildew

Example applications

Apples; Cucumber; Aubergine; Hops; Tomatoes; Vines; Pome fruit

Efficacy & activity

Availability status

Introduction & key dates

1960, developed in UK

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a plant protection agent

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

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

Chemical structure

Isomerism

A chiral molecule existing in the R- and S-forms. Substance is racemic.

Chemical formula

C₁₄H₁₈N₂O₇

Canonical SMILES

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

Isomeric SMILES

International Chemical Identifier key (InChIKey)

HDWLUGYOLUHEMN-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H18N2O7/c1-5-9(4)11-6-10(15(18)19)7-12(16(20)21)13(11)23-14(17)22-8(2)3/h6-9H,5H2,1-4H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Acaricide; Fungicide; Insecticide

Substance groups

Dinitrophenol insecticide; Dinitrophenol acaricide; Dinitrophenol fungicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Non-systemic, rapid contact action. Uncoupler of oxidative phosphorylation via disruption of proton gradient.

CAS RN

973-21-7

EC number

213-546-1

CIPAC number

223

US EPA chemical code

228700

PubChem CID

13783

CLP index number

006-028-00-X

Molecular mass

326.30

PIN (Preferred Identification Name)

rac-2-[(2R)-butan-2-yl]-4,6-dinitrophenyl propan-2-yl carbonate

IUPAC name

(RS)-2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate

CAS name

1-methylethyl 2-(1-methylpropyl)-4,6-dinitrophenyl carbonate

Other status information

Marine Pollutant; Phytotoxic to some crops including seedling cherries, blackcurrant

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

Physical state

Pale yellow crystals

Formulations

Property

Value

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

Example products using this active

Acrex

Formulation and application details

Often supplied as an emulsifiable liquid or a concentrate in an aromatic solvent

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3.97

at 25 °C

Low

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

1200000

Acetone

83000

Ethanol

89000

Xylene

19000

n-Hexane

Melting point (°C)

61.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

8.71 X 10⁰³

Calculated

Log P

3.94

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

0.9

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

Low volatility. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

1.64 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.8

Note

Green bean leaves, undercover, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

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)

Non-mobile

K_oc (mL g⁻¹)

4944

Notes and range

Estimated

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

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

Bio-concentration factor

BCF (l kg⁻¹)

300

Estimated

Threshold for concern

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

140

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

4.5

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

150

Gallus domesticus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

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

Soil micro-organisms

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)

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

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

> 50

Moderate

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)

Beneficial insects (Predatory mites)

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)

0.014

Oncorhynchus mykiss

High

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

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

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

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

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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)

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

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)

140

Rat

Moderate

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

3200

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.08

Rat 4 hr

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Toxic by inhalation and ingestion

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

General human health issues

Moderately toxic
Possible cardiovascular, liver and kidney toxicant
Consumption may cause yellow staining of skin

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2811

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

dinobuton

French

dinobuton

German

Dinobuton

Danish

dinobuton

Italian

dinobuton

Spanish

dinobuton

Greek

dinobuton

Polish

dinobuton

Swedish

Hungarian

Dutch

dinobuton

Norwegian

Record last updated:	29/08/2024
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