Dinobuton (Ref: OMS 1056)

Dinobuton (Ref: OMS 1056)	Last updated: 14/01/2021
(Also known as: ENT 27244; MC 1053; dinofen; UC 19786)

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

Unknown

Introduction & key dates

1960, developed in UK

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

Not applicable

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

Chemical structure

Isomerism

A chiral molecule existing in the R- and S-forms

Chemical formula

C₁₄H₁₈N₂O₇

Canonical SMILES

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

Isomeric SMILES

No data

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

Substance group

Dinitrophenol

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

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not known

Fungicide Resistance Classification (FRAC)

Not known

Examples of recorded resistance

Physical state

Pale yellow crystals

Related substances & organisms

tetradifon

Formulations

Property

Value

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

Acrex

Example products using this active

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)

Not expected to self ignite; Not highly flammable

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

8.71 X 10⁰³

Calculated

Log P

3.94

High

Bulk density (g ml⁻¹)

0.9

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

Low volatility

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

1.64 X 10^-03

Non-volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

4944

Notes and range

Estimated

Freundlich

K_f

K_foc

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

300

Estimated

Threshold for concern

CT₅₀ (days)

Not available

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 gallus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.014

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

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

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)

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

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)

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

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

European MRLs

EU MRL pesticide database

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Moderately toxic

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H301
Environment: H400, H410

EC Risk Classification

T - Toxic: R25
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S37, S45, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

2799

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

dinobuton

French

dinobuton

German

Dinobuton

Danish

dinobuton

Italian

dinobuton

Spanish

dinobuton

Greek

dinobuton

Polish

dinobuton

Swedish

Hungarian

Dutch

dinobuton

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