Dinobuton (Ref: OMS 1056)-Pesticide database

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Dinobuton (Ref: OMS 1056)

(Also known as: ENT 27244; MC 1053; dinofen; UC 19786)

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

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; Possible Reproduction/development effects

GENERAL INFORMATION

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

UK regulatory status

UK COPR regulatory status

Date COPR inclusion expires

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

EU Candidate for substitution (CfS)

Listed in EU database

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

Chemical structure

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?

Acaricide, Fungicide, Insecticide

Substance groups

Dinitrophenol insecticide; Dinitrophenol acaricide; Dinitrophenol fungicide

Minimum active substance purity

Known relevant impurities

Substance origin

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

US EPA chemical code

CLP index number

PIN (Preferred Identification Name)

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

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

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)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Pale yellow crystals

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

Source; quality score; and other information

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

V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source

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

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Melting point (°C)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source

Fat solubility of residues

Density (g ml⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source

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

Surface tension (mN m⁻¹)

Source; quality score; and other information

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

Dissipation rate RL₅₀ on plant matrix

Dissipation rate RL₅₀ on and in plant matrix

R3 R = Peer reviewed scientific publications
3 = Unverified data of known source

Green bean leaves, undercover, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

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

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Source; quality score; and other information

Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source

Notes and range

Notes and range

Source; quality score; and other information

GUS leaching potential index

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

Cannot be calculated

Potential for particle bound transport index

Potential for loss via drain flow

Bio-concentration factor

BCF (l kg⁻¹)

Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source

Threshold for concern

CT₅₀ (days)

Known metabolites

None

Terrestrial ecotoxicology

Source; quality score; and other information

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Mammals - Short term dietary NOEL

L1 L = Pesticide manuals and hard copy reference books / other sources
1 = Estimated data with little or no verification

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

Birds - Acute LD₅₀ (mg kg⁻¹)

L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source

Gallus domesticus

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

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)

Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source

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

Source; quality score; and other information

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data

Oncorhynchus mykiss

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)

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

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

Source; quality score; and other information

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Mammals - Inhalation LC₅₀ (mg l⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

Toxic by inhalation and ingestion

EU MRL pesticide database

GB MRL Register

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Specific human health issues

Endocrine disruptor

XNo, known not to cause a problem

A0 A = Chromosome aberration (EFSA database)
0 = No data

B0 B = DNA damage/repair (EFSA database)
0 = No data

C0 C = Gene mutation (EFSA database)
0 = No data

D0 D = Genome mutation (EFSA database)
0 = No data

E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data

Reproduction / development effects

Acetyl cholinesterase inhibitor

?Possibly, status not identified

XNo, known not to cause a problem

XNo, known not to cause a problem

Respiratory tract irritant

Skin sensitiser

?Possibly, status not identified

?Possibly, status not identified

?Possibly, status not identified

General human health issues

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

Handling issues

Value and interpretation

Not expected to autoignite; Not highly flammable
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

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