bromoxynil (Ref: ENT 20852) ** butil chlorofos ** bromotril ** bromoxynil phenol ** Translations

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SUMMARY

A widely used herbicide approved for use in the EU. It has a high aqueous solubility and is not considered to be volatile. The potential for leaching to groundwater is considered low, and it is not expected to be persistent in soil or water systems. It is highly toxic to mammals, is an endocrine distrupter and may cause negative reproduction or development effects. It is moderately toxic to most aquatic and terrestrial biodviersity. The main exceptions are a low toxicity to algae and honeybees by the contact route (not the oral route).

GENERAL INFORMATION
for bromoxynil

Description: An HBN herbicide used for post-emergence control of annual broad-leaved weeds. it is also a pesticide transformation product

Example pests controlled: Pigweed; Mayweed; Knotweed; Shepherd's purse; Goosefoot; Morning glory; Dwarf marigold; Stinkweed; Cocklebur; Wild radish

Example applications: Cereals including wheat, barley, oats; Lucerne; Corn; Sorghum; Onions; Flax; Mint; Turf; Non-crop land

Efficacy & activity: Proved as effective by extensive use over a prolonged period and via field experiments

Availability status: Current

Introduction & key dates: 1963, first reported.

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

Also used in: Australia

Chemical structure:

Isomerism	None
Chemical formula	C7H3Br2NO
Canonical SMILES	C1=C(C=C(C(=C1Br)O)Br)C#N
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	UPMXNNIRAGDFEH-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams:

Common Name	Relationship	Link
Bromoxynil	-

General status:

Pesticide type	Herbicide, Metabolite
Metabolite Type	Soil
Substance group	Hydroxybenzonitrile
Minimum active substance purity	970 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Selective, contact action with some systemic activity. Inhibits photosynthesis (photosystem II).
CAS RN	1689-84-5
EC number	216-882-7
CIPAC number	87
US EPA chemical code	035301
PubChem CID	15531
Molecular mass (g mol-1)	276.9
PIN (Preferred Identification Name)	3,5-dibromo-4-hydroxybenzonitrile
IUPAC name	3,5-dibromo-4-hydroxybenzonitrile
CAS name	3,5-dibromo-4-hydroxybenzonitrile
Other status information	Marine Pollutant; PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards	UK Environment Agency non-statutory standard for the protection of aquatic life: freshwater and saltwater annual average 100 ug/L; max acceptable conc: 1000 ug/L
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	Clear to white crystalline solid
Related substances & organisms	diflufenican ioxynil ethofumesate mecoprop-P prosulfuron terbuthylazine

Can be a metabolite of:

Parent		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
bromoxynil octanoate		Soil	0.446	Major fraction, Relevant
bromoxynil heptanoate		Soil	0.317	Major fraction, Relevant
bromoxynil butanoate		Soil	0.379	Major fraction, Relevant

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Barclay Nufarm Dow AgroSciences
Example products using this active	Emblem Brominex Chipco Buctril Brominal Plus
UK LERAP status	Buffer probably required in UK - see product label
Formulation and application details	Spray application.

ENVIRONMENTAL FATE
for bromoxynil

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		38000	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		186000	A5 - Acetone	-
		80500	A5 - Methanol	-
		46700	A5 - n-Octanol	-
		51100	A5 - Acetonitrile	-
Melting point (oC)		190.5	A5	-
Boiling point (oC)		Decomposes before boiling	A4	-
Degradation point (oC)		270	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.86 X 1000	Calculated	-
	Log P	0.27	A5	Low
Bulk density (g ml-1)/Specific gravity		1.63	A5	-
Dissociation constant (pKa) at 25oC		3.86	A5	-
		Note: Weak acid
Vapour pressure at 20oC (mPa)		0.12	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		8.7 X 10-07	A5	Non-volatile
GUS leaching potential index		0.03	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	5.30 X 10-04	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		In methanol: 221.2nm = 30343, 286.8nm = 18302, 295.0nm=16215	A5	-
Surface tension (mN m-1)		73.0	A5 at 20 degC, 90%	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	1.04	A5	Non-persistent
	DT50 (lab at 20oC)	1.04	A5	Non-persistent
	DT50 (field)	8	Y4	Non-persistent
	DT90 (lab at 20oC)	5.16	A5	-
	DT90 (field)	-	-	-
	DT50 modelling endpoint	-	-	-
	Note	EU 2017 dossier lab studies DT50 range 0.15-4.42 days, DT90 range 0.60-24.17 days, Soils=17; Other sources: field studies from literature (R3), generally DT50 7-10 days (Q3)
Dissipation rate RL50 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL50 on and in plant matrix	Value	2.2	R4	-
	Note	Published literature RL50 range 1.1-3.2 days, 2 field crops, various matrices, n=2
Aqueous photolysis DT50 (days) at pH 7	Value	0.5	A5	Fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	-
Water-sediment DT50 (days)		13	A5	Fast
Water phase only DT50 (days)		13	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	R3	Moderately mobile
	Koc	302
	Notes and range	-
Freundlich	Kf	2.84	A5	Moderately mobile
	Kfoc	127.2
	1/n	0.98
	Notes and range	EU 2017 dossier kf range 0.8-5.9 mL/g; Kfoc range 57-256 mL/g; 1/n range 0.937-1.009, Soils=5
pH sensitivity		Yes - lower mobility at low pH

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
3,5-di-bromo-4-hydroxybenzoic acid		Soil	0.348	Major fraction, Relevant
3,5-di-bromo-4-hydroxybenzamide		Soil	0.216	Major fraction, Relevant

ECOTOXICOLOGY
for bromoxynil

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	Low risk	A5 Based on LogP < 3	Low potential
	CT50 (days)	-		-
Mammals - Acute oral LD50 (mg kg-1)		130	A5 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	16.6	L2 Rat, 2 year	High
	(ppm diet)	100		-
Birds - Acute LD50 (mg kg-1)		217	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		1380 mg kg feed-1	A5 Anas platyrhynchos	-
Fish - Acute 96 hour LC50 (mg l-1)		29.2	A5 Lepomis macrochirus	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		2.0	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		12.5	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		3.1	A5 Daphnia magna	Moderate
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)		0.033	A5 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.12	A4 Navicula pelliculosa, 72 hour	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		3.13	F4 Green algae population study	Low
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	150	A5 Apis mellifera	Low
	Oral acute 48 hour LD50 (μg bee-1)	10.9	A5 Apis mellifera	Moderate
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		45	A5 Eisenia foetida	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		4.5	A5 Eisenia foetida	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	17.9 -23.6	Mortality Parasitism Dose: 0.45 kg ha-1 A3 Aphidius rhopalosiphi, adults	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	0	Mortality Dose: 0.45 kg ha-1 A3 Typhlodromus pyri	-
Soil micro-organisms		Nitrogen mineralisation: Low, transient effect Carbon mineralisation: Low, transient effect	A5 {Dose: 3.73 mg kg-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for bromoxynil

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)		130	A5 Rat	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		0.15	A5 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.03	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.013	A5 Rat, SF=300	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		0.013	A5 Rat, SF=300	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.003	A5 Dog, SF=100	-
Dermal penetration studies (%)		3.5	A5	-
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	Low risk from registered uses with PPE/PPC, High risk without PPE/PPC
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		USEPA - possible human carcinogen Possible liver and thyroid 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, H330, H360d Environment: H400, H410
EC Risk Classification		Reproduction risk category 3: R63 T+ - Very toxic: R26 T - Toxic: R25 Xn - Harmful: R43 N - Dangerous for the environment: R50, R53
EC Safety Classification		S1/2, S27/28, S36/37, S45, S60, S61, S63
WHO Classification		II	-	Moderately hazardous
US EPA Classification (formulation)		II	-	Warning - Moderately toxic
UN Number		2588
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for bromoxynil

Language	Name
English	bromoxynil
French	bromoxynil
German	Bromoxynil
Danish	bromoxynil
Italian	bromoxinil
Spanish	bromoxinil
Greek	bromoxynil
Slovenian	bromoksinil
Polish	bromoksynil
Swedish	-
Hungarian	bromoxynil
Dutch	bromoxynil

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Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk