benfluralin (Ref: EL-110) ** bethrodine ** benfuraline ** benefin ** benthrodine ** balan ** Translations

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SUMMARY

Benfluralin is a pre-emergence herbicide that has EU regulatory approval for use. It has a low aqueous solubility and is quite volatile. It is not expected to leach to groundwater. It is moderately persistent in soil systems and not usually persistent in water. It has a low mammalian toxicity but there is concern regarding its potential to bioaccumulate. It is moderately toxic to birds, honeybees, earthworms and most aquatic organisms.

GENERAL INFORMATION
for benfluralin

Description: A pre-emergence herbicide used for grass and other weed control in a range of edible and non-food crops

Example pests controlled: Johnssongrass; Chickweed; Lambsquarter; Purslane; Knotweed; Clover; Pigweed; Plantains

Example applications: Alfalfa; Turf; Lettuce; Ornamentals including Christmas trees; Non-bearing fruit and nut trees; Non-cropped areas such as rights-of-way, pavements, railways

Availability status: Current

Introduction & key dates: 1963, USA

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	Belgium
Date inclusion expires	28/02/2019

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

General status:

Pesticide type	Herbicide
Substance group	Dinitroaniline
Minimum active substance purity	960 kg/kg
Known relevant impurities	EU dossier - ethyl-butyl-nitrosamine: < 0.1 mg/kg
Substance origin	Synthetic
Mode of action	Microtubule assembly inhibition
CAS RN	1861-40-1
EC number	217-465-2
CIPAC number	285
US EPA chemical code	084301
Chiral molecule	No
Chemical formula	C13H16F3N3O4
SMILES	[O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCCC)CC)C(F)(F)F
International Chemical Identifier key (InChIKey)	SMDHCQAYESWHAE-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C13H16F3N3O4/c1-3-5-6-17(4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	335.28
PIN (Preferred Identification Name)	N-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline
IUPAC name	N-butyl-N-ethyl-α,α,α-trifluoro-2,6-dinitro-p-toluidine
CAS name	N-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)benzenamine
Other status information	OSPAR soc
Herbicide Resistance Classification (HRAC)	K1
Herbicide Resistance Classification (WSSA)	3
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	-
Physical state	Colourless to yellow crystals depending on purity
Related substances & organisms	ethyl butyl nitrosamine oryzalin trifluralin

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Sigma-Aldrich Dow AgroSciences Helena Chemical Co Makhteshim Agan
Example products using this active	Bonalan Carpidor Benefex Emblem Balan
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Often available as an emulsifiable concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE
for benfluralin

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.065	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		250000	A5 - Xylene	-
		39100	A5 - Methanol	-
		250000	A5 - Acetone	-
		250000	A5 - Ethyl acetate	-
Melting point (oC)		66.4	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		205	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.55 X 1005	Calculated	-
	Log P	5.19	A5	High
Bulk density (g ml-1)/Specific gravity		1.42	A5	-
Dissociation constant (pKa) at 25oC		-0.59	A5 -	-
		Note: Very strong acid
Vapour pressure at 25oC (mPa)		1.73	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		9.1	A5	Moderately volatile
Henry's law constant at 20oC (dimensionless)		3.66 X 10-03	Calculated	Volatile
GUS leaching potential index		-0.05	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	5.35 X 10-03	Calculated	-
	Note	Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW
Potential for particle bound transport index		-	Calculated	High
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 239nm = 9180, 283nm = 8010; [Acidic solution: 248nm = 4390, 298nm = 4580, 448nm = 3870; [Basic solution: 238nm = 7550, 283nm = 6370, 431nm = 3720	A5	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	40	W4	Moderately persistent
	DT50 (lab at 20oC)	38.2	A5	Moderately persistent
	DT50 (field)	53	A5	Moderately persistent
	DT90 (lab at 20oC)	199	A5	-
	DT90 (field)	175	A5	-
	Note	EU dossier lab studies DT50 range 20-86 days, DT90 range 89.7-385 days; field studies DT50 range 34-73 days, DT90 range 115-242 days
Plant matrix DT50 (days)	Value	61.6	R4	-
	Note	Turfgrass, leaves
Aqueous photolysis DT50 (days) at pH 7	Value	0.1	A5	Fast
	Note	Unstable in UV light
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 4 to pH 9
Water-sediment DT50 (days)		1.2	A5	Fast
Water phase only DT50 (days)		0.75	A5	Fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	A5	Non-mobile
	Koc	10777
	Notes and range	EU dossier 8519-14400 mL/g; Other literature Koc range 4000-10,700 mL/g
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	91/414 relevancy
2,6-dinitro-4-(trifluoromethyl)phenol		Soil	0.052	Minor, Relevancy unknown

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
3-nitro-5(trifluoromethyl)-1,2-benzenediamine	des-alkylbenfluralin diamine	Water (Photolysis)	0.115	-
4-nitro-2-propyl-6-(trifluoromethyl)-1H-benzimidazole	propyl benzimidazole	Water (Photolysis)	0.164	-
2-methyl-4-nitro-6-(trifluoromethyl)-1H-benzimidazole	methyl benzimidazole	Water (Photolysis)	0.114	-
1-ethyl-7-nitro-2-prpyl-5-(trifluoromethyl)-1H-benzimidazole	ethyl propyl benzimidazole; U6#1	Water (Photolysis)	0.195	-
N2-butyl-N2-ethyl-3-nitro-5-(trifluoromethyl)-benzene-1,2-diamine	benfluralin diamine	Rat	-	-
N2-butyl-N2-ethyl-5-(trifluoromethyl)-1,2,3-benzenetriamine	-	Rat	-	-

ECOTOXICOLOGY
for benfluralin

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	1572	A5 Whole fish	Threshold for concern
	CT50 (days)	1.3		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	0.5	L3 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 5000 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		0.081	A5 Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l-1)		0.0019	A5 Oncorhynchus mykiss	High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 100	A5 Daphnia magna	Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.0155	A5 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.043	A5 Americamysis bahia	High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		0.231	A5 Chironomus riparius	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		0.112	A5 Chironomus riparius	Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		0.02	A5 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		> 100	A5 Pseudokirchneriella subcapitata	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 110.7	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 500	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		30.8	A3 Eisenia foetida, 8 week corr	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	5.5	A5 Folsomia candida, 28 day NOEC mg kg-1	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	3.4 -18.4	Mortality Reproduction Dose: 0.084 l ha-1 A5 Typhlodromus pyri, protonymphs	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	100.0	Mortality Dose: 0.084 l ha-1 A5 Aphidius rhopalosiphi	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 45 l product ha-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for benfluralin

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)		> 5000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 5000	A5 Rabbit	-
Mammals - Inhalation LC50 (mg l-1)		2.16	A5 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.005	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.005	A5	-
Dermal penetration studies (%)		0.6-4.5	A5 concentration dependant	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Negligible risk to bystanders
	Occupational	PPE/PPC required for operators and other farm workers
European MRLs		Click here for the EU MRL pesticide database
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 and kidney 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		Not explosive or oxidising
CLP classification 2013		-
EC Risk Classification		Carcinogen category 3: R40 Xn - Harmful: R43 Xi - Irritant: R38, R36
EC Safety Classification		-
WHO Classification		U	-	Unlikely to present an acute hazard
US EPA Classification (formulation)		-	-
UN Number		Usually 3077
Waste disposal & packaging		-

TRANSLATIONS
for benfluralin

Language	Name
English	benfluralin
French	benfluraline
German	Benfluralin
Danish	benfluralin
Italian	benfluralin
Spanish	benfluralina
Greek	-
Slovenian	benfluralin
Polish	benfluralina
Swedish	-
Hungarian	benfluralin
Dutch	-

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Record last updated: Monday 15 August 2016
Contact: aeru@herts.ac.uk