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bromoxynil butanoate
** bromoxynil butyrate ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

SUMMARY

A widely used herbicide approved for use in the EU. It has a low aqueous solubility and a low volatility. There is a low potential for leaching to groundwater based on its chemical properties. It is not expected to be persistent in soil or water systems. It is moderately toxic via the oral route to mammals, is an endocrine distrupting chemical and a skin sensitiser. It is highly toxic to fish but less so to other aquatic and terresitial biodiversity.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for bromoxynil butanoate

Description: An HBN herbicide used for post-emergence control of annual broad-leaved weeds

Example pests controlled: Ragweed; Smartweed; Nightshade; Kochia; Wild mustard

Example applications: Alfalfa; Garlic; Corn; Sorghum; Cereals including wheat, barley; Turf; Non-cropped areas including rights-of-way, pathways

Efficacy & activity: Efficiacy proven from prolonged use in the EU and from experimental studies

Availability status: Current

Introduction & key dates: circa 1980

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur France/Germany
Date inclusion expires 31/07/2019
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia, Latin America, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism None
Chemical formula C11H9Br2NO2
Canonical SMILES CCCC(=O)OC1=C(C=C(C=C1Br)C#N)Br
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) PGMZYNZXIYOOHJ-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C11H9Br2NO2/c1-2-3-10(15)16-11-8(12)4-7(6-14)5-9(11)13/h4-5H,2-3H2,1H3
2D structure diagram/image available? Yes

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Bromoxynil Parent Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Hydroxybenzonitrile
Minimum active substance purity 967 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Select contact action with some systemic activity. Inhibits photosynthesis (photosystem II).
CAS RN 3861-41-4
EC number 223-374-9
CIPAC number 87.403
US EPA chemical code -
PubChem CID 62526
Molecular mass (g mol-1) 347.0
PIN (Preferred Identification Name) 2,6-dibromo-4-cyanophenyl butanoate
IUPAC name 2,6-dibromo-4-cyanophenyl butyrate
CAS name 2,6-dibromo-4-cyanophenyl butanoate
Other status information Marine Pollutant; PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) C3
Herbicide Resistance Classification (WSSA) 6
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Light beige coloured powdery solid
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically -
Example products using this active -
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details Spray application.


ENVIRONMENTAL FATE

for bromoxynil butanoate

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 5.4 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 70000 A4 - Ethanol -
23000 A5 - n-Hexane -
600000 A5 - Toluene -
600000 A5 - Acetone -
Melting point (oC) 86 A5 -
Boiling point (oC) 353 A5 -
Degradation point (oC) 320 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 7.24 X 1003 Calculated -
Log P 3.86 A5 High
Bulk density (g ml-1)/Specific gravity - - -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.28 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.80 X 10-02 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index - - -
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value - - -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Low
Maximum UV-vis absorption L mol-1 cm-1 In methanol: 213nm= 48122, 283nm=723, 294nm=633 A5 -
Surface tension (mN m-1) 68.60 A5 at 20 degC, 97.6% -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 0.58 Click here to see a warning relating to modelling and this active substance A5 Non-persistent
DT50 (lab at 20oC) 0.58 A5 Non-persistent
DT50 (field) - - -
DT90 (lab at 20oC) 1.99 A5 -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note EU 2017 dossier lab studies DT50 range 0.5-0.67 days, DT90 range 1.69-2.29 days, Soils =2
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 0.12 A5 Fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 33 A5 Moderately persistent
Note DT50: pH 4: 44 days; pH 9: 1.1 days
Water-sediment DT50 (days) - - -
Water phase only DT50 (days) - - -

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
bromoxynil (Ref: ENT 20852) This metabolite may cause environmental pollution, click here for further information Soil   0.379   Major fraction, Relevant
3,5-di-bromo-4-hydroxybenzamide This metabolite may cause environmental pollution, click here for further information Soil   0.150   Major fraction, Relevant
3,5-di-bromo-4-hydroxybenzoic acid Soil   0.057   Major fraction, Relevant


ECOTOXICOLOGY

for bromoxynil butanoate

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) - - -
CT50 (days) - -
Mammals - Acute oral LD50 (mg kg-1) 116 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) 420 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.032 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.008 A5 Pimephales promelas High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.208 A5 Daphnia magna Moderate
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) 0.15 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.75 A5 Navicula pelliculosa, 96 hr Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) 199 A4 Apis mellifera, unknown test duration Low
Oral acute 48 hour LD50 (μg bee-1) 76.4 A4 Apis mellifera, unknown test duration Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) - - -
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 2.3 A4 Eisenia foetida, EC10 corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect - - -
Other arthropod (2) LR50 g ha-1 - - -
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: Low, transient effect A5 {Dose: 2.57 mg kg-1, 28 days -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for bromoxynil butanoate

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) 116 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.217 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.01 A5 Mouse, 18 mnths, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.04 A5 SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.01 A5 Dog, SF=100 -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded
Occupational -
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues Possible liver toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes IMDG Transport Code is usually 6.1
Not explosive or oxidising
CLP classification 2013 Health: H301, H317, H319, H332, H360d
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 3: R63
Xn - Harmful: R20/22, R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S36/37, S46, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number Usually 2558
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for bromoxynil butanoate

Language Name
English bromoxynil butanoate
French -
German -
Danish -
Italian -
Spanish -
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk