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Dinoseb (Ref: HOE 26150)
(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 know irritant. It is highly toxic to birds, moderately toxic to fish but presents less of a risk to honeybees.
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
Environmental fate
High alert:
GUS: High leachability; Drainflow: Mobile
Ecotoxicity
High alert:
Birds acute ecotoxicity: High; Fish acute ecotoxicity: High; Fish chronic 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
-
Availability status
Considered obsolete but may be available in some countries; Banned in many countries
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
                 
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
A chiral molecule. Substance is racemic.
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
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); 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
Dark reddish brown solid or orange viscous liquid depending upon temperature
Related substances & organisms
Formulations
Property
Value
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.
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. Available online but no longer updated. (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. Dataset is no longer available.
4 = Verified data
 Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.35
Q2 Q = Miscellaneous data from online sources
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. Dataset is no longer available.
4 = Verified data
 -
Weak acid
Vapour pressure at 20 °C (mPa)
6.7
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (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. Dataset is no longer available.
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. Available online but no longer updated. (click here )
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
30
Q2 Q = Miscellaneous data from online sources
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. Dataset no longer available.
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. Dataset is no longer available.
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 -
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 -
Known metabolites

None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
25
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (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 / FAO data, IPCS INCHEM data (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)
- - -
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)
0.044
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (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 / FAO data, IPCS INCHEM data (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 / FAO data, IPCS INCHEM data (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 / FAO data, IPCS INCHEM data (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)
- - -
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 / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Chlamydomonas moewusii 7 day		 Low
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. Available online but no longer updated. (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)
- - -
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
?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
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
-
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