Dinoseb acetate (Ref: HOE 02904)	Last updated: 21/09/2023
(Also known as: DNBPA)

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SUMMARY

Dinoseb acetate is a banned herbicide that was once widely used. It has a high aqueous solubility and is volatile. It is highly toxic to mammals and may cause development/reproduction effects. Dinoseb is also a known irritant.

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
		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	-
Availability status	Considered obsolete but may be available in some countries; Banned in many countries
Introduction & key dates	1960, first reported

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Not applicable
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	Not applicable
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 acetate is a chiral molecule. Substance is racemic.
Chemical formula	C₁₂H₁₄N₂O₆
Canonical SMILES	CCC(C)C1=CC(=CC(=C1OC(=O)C)[N+](=O)[O-])[N+](=O)[O-]
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	RDJTWDKSYLLHRW-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C12H14N2O6/c1-4-7(2)10-5-9(13(16)17)6-11(14(18)19)12(10)20-8(3)15/h5-7H,4H2,1-3H3
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
dinoseb	Parent

General status

Pesticide type	Herbicide
Substance groups	Dinitrophenol herbicide
Minimum active substance purity	>94%
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Inhibits respiratory electron transport, and uncouples oxidative phosphorylation - membrane disruption. Selective, non-systemic. Contact action.
CAS RN	2813-95-8
EC number	No data found
CIPAC number	403
US EPA chemical code	-
PubChem CID	17776
CLP index number	609-025-00-7
Molecular mass	282.2
PIN (Preferred Identification Name)	rac-2-[(2R)-butan-2-yl]-4,6-dinitrophenyl acetate
IUPAC name	(RS)-2-sec-butyl-4,6-dinitrophenyl acetate
CAS name	2-(1-methylpropyl)-4,6-dinitrophenyl acetate
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 Classification (HRAC)	M
Herbicide Resistance Classification (WSSA)	24
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	-
Physical state	Brown coloured oil
Related substances & organisms	dinoseb dinoseb sodium dinoseb trolamine dinoseb acetate

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Hoechst Rhone-Poulenc
Example products using this active	Ivosit Phenotan
Formulation and application details	Available in a variety of formulations including emulsifiable concentrates and wettable powders

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		2200	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		26	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Boiling point (°C)		170	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	-	-	-
	Log P	-	-	-
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		28.0	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Highly volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
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	-	-	-
	Note	-
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	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	-	-	-
	Kfoc	-
	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		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
dinoseb (Ref: HOE 26150)	-	-	-

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 60	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source 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)		-	-	-
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)	-	-	-
	Chronic	-	-	-
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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
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

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)		> 60	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		1.3	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
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 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 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 ; E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ✓Yes, known to cause a problem XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser No data found ✓Yes, known to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem No data found
General human health issues		Highly toxic

Handling issues

Property	Value and interpretation
General	Incompatible with alkaline substances
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 acetate
French	dinoseb ace
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	21/09/2023
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