Dinoseb (Ref: HOE 26150)	Last updated: 16/01/2021
(Also known as: DNBP; dinosebe; dinitro-general; DN 289)

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SUMMARY

Dinoseb is a banned 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 know irritant. It is highly toxic to birds, moderately toxic to fish but presents less of a risk to honeybees.

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	Obsolete, Banned
Introduction & key dates	1945, first reported

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)	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

Also used in

Also used in	-

Chemical structure

Isomerism	A chiral molecule
Chemical formula	C₁₀H₁₂N₂O₅
Canonical SMILES	CCC(C)C1=CC(=CC(=C1O)[N+](=O)[O-])[N+](=O)[O-]
Isomeric SMILES	No data
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 group	Dinitrophenol
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	46
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
Other status information	Chemical subject to PIC regulations; Marine Pollutant; Rotterdam Convention (Class O)
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	Dark reddish brown solid or orange viscous liquid depending upon temperature

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Aretit Ivosit Supersevtox Premerge Caldon: Chemox Subitex Nitrapone
Example products using this active	DowElanco Hoeschst Schering
Formulation and application details	Available in a variety of formulations including soluble liquids and emulsifiable concentrates.

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		52	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data	Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)		480000	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source Ethanol	-
		270000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Ethanol	-
Melting point (°C)		38	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)		177	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.95 X 1002	Calculated	-
	Log P	2.29	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	Low
Bulk density (g ml⁻¹)		1.35	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source	-
Dissociation constant pKa) at 25 °C		4.62	DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. MS in preparation 4 = Verified data	-
		Weak acid
Vapour pressure at 20 °C (mPa)		6.7	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data	Moderately volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		6.01 X 10-04	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	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)	18	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data	Non-persistent
	DT₅₀ (lab at 20 °C)	30	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source	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 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	Stable	T4 T = UN EPFA database 4 = Verified data	Stable
	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	-	H3 H = The US ARS pesticide properties database (click here ) 3 = Unverified data of known source	Mobile
	Koc	30
	Notes and range	Other sources: 117-123 mL g⁻¹ (R3)
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		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	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	1.8	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source (whole body)	Low potential
	CT₅₀ (days)	Not available		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		25	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data 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	F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source Anas platyrhynchos	High
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.044	G3 G = Extension Toxicology network database EXTOXNET (click here ) 3 = Unverified data of known source Salmonidae	High
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.059	F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source Pimephales promelas 32 day	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.24	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)		0.170	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data 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 - 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)		1.201	F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source Chlamydomonas moewusii 7 day	Low
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)	Highly toxic	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Highly toxic
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	-	-	-
	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)		25	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data 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)		0.0011	F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source	-
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
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 ?Possibly, status not identified A3 A = Chromosome aberration (EFSA database) 3 = Negative ; 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 hazardous USEPA - possible human carcinogen

Handling issues

Property	Value and interpretation
General	An oxidising agent
CLP classification 2013	Health: H301, H311, H319, H360Df Environment: H400, H410
EC Risk Classification	Reproduction risk category 2 and 3: R62, R61 T - Toxic: R24/25 Xi - Irritant: R36 H - Handling risks: R44 N - Dangerous for the environment: R50, R53
EC Safety Classification	S45, S53, S60, S61
WHO Classification	Ib (Highly hazardous / Highly hazardous)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	dinoseb
French	dinosèbe
German	Dinoseb
Danish	dinoseb
Italian	dinoseb
Spanish	dinoseb
Greek	dinoseb
Polish	dinoseb
Swedish	-
Hungarian	-
Dutch	dinoseb

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Record last updated:	16/01/2021
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