Dinoseb (Ref: HOE 26150)

Dinoseb (Ref: HOE 26150)	Last updated: 28/08/2025
(Also known as: DNBP; dinosebe; dinitro-general; DN 289)

SUMMARY

Dinoseb is a herbicide that was once widely used. It has a moderate aqueous solubility, is volatile and has a high potential for leaching to groundwater. It is not generally persistent in soil systems but can be persistent in water. It is highly toxic to mammals and may cause development/reproduction effects. Dinoseb is also a known irritant. It is highly toxic to birds, moderately toxic to fish but presents less of a risk to honeybees.

Hazard 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. These hazard alerts do not take account of usage patterns or exposure, thus do not represent risk.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: GUS: High leachability; Drainflow: Mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High; Fish acute ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Reproduction/development effects

GENERAL INFORMATION

Description

An obsolete dinitrophenol herbicide that was used for post-emergence weed control in a variety of crops including cereals, vegetables and some soft fruit

Example pests controlled

Crabgrass; Barnyardgrass; Pigweed; Lambsquarters; Foxtails; Sorrel

Example applications

Soybeans; Cereals; Cotton; Fruit including citrus, grapes, bluebrries, currants, gooseberries; Nuts; Lucerne

Efficacy & activity

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

Dinoseb exhibits optical isomerism due to the presence of a chiral centre in its sec-butyl side chain. This chiral carbon is bonded to four different groups, allowing the molecule to exist as two enantiomers. In practice, dinoseb is often encountered as a racemic mixture, containing equal amounts of both enantiomers.

Chemical formula

C₁₀H₁₂N₂O₅

Canonical SMILES

CCC(C)C1=CC(=CC(=C1O)[N+](=O)[O-])[N+](=O)[O-]

Isomeric SMILES

International Chemical Identifier key (InChIKey)

OWZPCEFYPSAJFR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
dinoseb	Unstated isomer

General status

Pesticide type

Herbicide

Substance groups

Dinitrophenol herbicide

Minimum active substance purity

>95%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Contact. Inhibits respiratory electron transport and is an uncoupler of oxidative phosphorylation via disruption of proton gradient - membrane disruption.

CAS RN

88-85-7

EC number

201-861-7

CIPAC number

US EPA chemical code

037505

PubChem CID

6950

CLP index number

609-025-00-7

Molecular mass

240.22

PIN (Preferred Identification Name)

rac-2-[(2R)-butan-2-yl]-4,6-dinitrophenol

IUPAC name

(RS)-2-sec-butyl-4,6-dinitrophenol

CAS name

2-(1-methylpropyl)-4,6-dinitrophenol

Forever chemical

Other status information

Marine Pollutant; Rotterdam Convention (Class O) - subject to PIC regulations; Subject to the provisions of the UK Poisons Act 1972

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Dark reddish brown solid or orange viscous liquid depending upon temperature

Related substances & organisms

dinoseb acetate

dinoseb ammonium

dinoseb diolamine

dinoseb sodium

Commercial

Property

Value

Availability status

Considered obsolete but may be available in some countries; Banned in many countries

Introduction & key dates

1945, first reported; 1986, withdrawn EU & USA

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

DowElanco
Hoeschst
Schering

Example products using this active

Aretit
Ivosit
Supersevtox
Premerge
Caldon: Chemox
Subitex
Nitrapone

Formulation and application details

Available in a variety of formulations including soluble liquids and emulsifiable concentrates.

Commercial production

The production of dinoseb typically involves a multi-step synthesis starting from phenol. First, phenol undergoes alkylation with sec-butyl halide (such as sec-butyl chloride) in the presence of a Lewis acid catalyst like aluminium chloride, introducing the sec-butyl group at the ortho position. This is followed by nitration, where the alkylated phenol is treated with a mixture of concentrated nitric and sulfuric acids to introduce nitro groups at the 4 and 6 positions of the aromatic ring. The reaction conditions are carefully controlled to avoid over-nitration or degradation of the product. After nitration, the crude product is purified through recrystallisation or other separation techniques to yield the final compound.

Impact on climate of production and use

Data for the amount of life cycle GHGs produced by dinoseb are not available in the public domain. However, whilst estimates vary, more general data suggests that between 18 and 27 kilograms of CO₂e is emitted per kilogram of herbicide produced.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Moderate

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

480000

Ethanol

270000

Ethanol

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

177

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

1.95 X 10⁰²

Calculated

Log P

2.29

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.35

Dissociation constant pKa) at 25 °C

4.62

Weak acid

Vapour pressure at 20 °C (mPa)

6.7

Moderately volatile. 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)

6.01 X 10^-04

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)

Non-persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature data indicates DT₅₀ of 2 to 6 weeks

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Stable

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)

Mobile

K_oc (mL g⁻¹)

Notes and range

Other sources: 117-123 mL g⁻¹ (R3)

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

3.73

Calculated

High leachability

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

Value

6.36 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

1.8

Whole body

Low potential

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)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

9.5

Anas platyrhynchos

High

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

Vegetative vigour ER₅₀ (g ha⁻¹)

Seedling emergence ER₅₀ (g ha⁻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)

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)

0.044

Salmonidae spp.

High

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

0.059

Pimephales promelas 32 day

Moderate

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

0.19

Danio rerio Embryo

Moderate

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

0.24

Daphnia magna

Moderate

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)

0.170

Americamysis bahia

Moderate

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, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹)

Algae - Chronic (growth rate, fresh; mg l⁻¹) (7 day NOEC)

1.201

Chlamydomonas moewusii

Low

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)

Rat

High

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

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

Minimal risk at current time due to substance being obsolete

Occupational

Readily absorbed through the skin - PPE/PPC required

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

Highly hazardous
US EPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

An oxidising agent

CLP classification 2013

Health: H301, H311, H319, H360Df
Environment: H400, H410

WHO Classification

Ib (Highly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

dinoseb

French

dinosèbe

German

Dinoseb

Danish

dinoseb

Italian

dinoseb

Spanish

dinoseb

Greek

dinoseb

Polish

dinoseb

Swedish

Hungarian

Dutch

dinoseb

Norwegian

Record last updated:	28/08/2025
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