| bromoxynil butanoate |
 |
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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 
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: 
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 |
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Also used in: Australia, Latin America, USA
Chemical structure:
| 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 |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Bromoxynil | Parent |  |
General status:
| 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 |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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  |
- | - | - | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | - | - | - |
| Note | - | |||
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 0.58 |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
|
| bromoxynil (Ref: ENT 20852) |
Soil | 0.379 | Major fraction, Relevant | |
| 3,5-di-bromo-4-hydroxybenzamide |
Soil | 0.150 | Major fraction, Relevant | |
| 3,5-di-bromo-4-hydroxybenzoic acid | Soil | 0.057 | Major fraction, Relevant | |
ECOTOXICOLOGY
for bromoxynil butanoate
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (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 | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
IMDG Transport Code is usually 6.1 Not explosive or oxidising |
|||
| CLP classification 2013 | Health: H301, H317, H319, H332, H360d Environment: H400, H410 |
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| EC Risk Classification |
Reproduction risk category 3: R63 Xn - Harmful: R20/22, R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
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 |
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