Fluoroglycofen	Last updated: 19/12/2024
(Also known as: fluoroglycofene; benzofluorfen)

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SUMMARY

Fluoroglycofen is a nitrophenyl ether compound used as a post-emergence herbicide. It has a low aqueous solubility and a low volatility. Under most conditions it tends not to be environmentally persistent. It is moderately toxic to mammals via the oral route. Information on chronic health risks is missing. It is highly toxic to birds and algae but less so to other species.

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 Moderate alert: Moderately persistent; GUS: Transition state; Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity High alert: Earthworms acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects Warning: Significant data are missing

GENERAL INFORMATION

Description	A nitrophenyl ether post-emergence herbicide for the control of mainly annual weeds
Example pests controlled	Grasses, Broad-leaved weeds
Example applications	Cereals including wheat, barley, oats; Rice; Peanuts; Soyabeans
Efficacy & activity	-
Availability status	Current
Introduction & key dates	1987, registered USA

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
GB LERAP status	No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	-
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	-
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	South Africa

Chemical structure

Isomerism	None
Chemical formula	C₁₆H₉CIF₃NO₇
Canonical SMILES	C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)OCC(=O)O
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	DHAHEVIQIYRFRG-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C16H9ClF3NO7/c17-11-5-8(16(18,19)20)1-4-13(11)28-9-2-3-12(21(25)26)10(6-9)15(24)27-7-14(22)23/h1-6H,7H2,(H,22,23)
2D structure diagram/image available?	Yes

General status

Pesticide type	Herbicide
Substance groups	Diphenyl ether herbicide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Induces the accumulation of tetrapyroles which attack plant cells. Inhibition of protoporphyrinogen oxidase (PPO) - cell membrane disruption
CAS RN	77501-60-1
EC number	616-467-4
CIPAC number	523
US EPA chemical code	-
PubChem CID	92395
CLP index number	No data found
Molecular mass	419.69
PIN (Preferred Identification Name)	O-(5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoyl)glycolic acid
IUPAC name	O-(5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoyl)glycolic acid
CAS name	carboxymethyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Class (HRAC MoA class)	E
Herbicide Resistance Class (WSSA MoA class)	14
Insecticide Resistance Class (IRAC MoA class)	Not applicable
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	-
Physical state	Dark amber solid

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Rohm and Haas Dow AgroScience
Example products using this active	Estrad Trenox Duplo Compete Simitar
Formulation and application details	Usually supplied as an emulsifiable concentrate and wettable powder.

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		0.6	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		10000	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data Hexane	-
Melting point (°C)		65	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)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	4.47 X 1003	Calculated	-
	Log P	3.65	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	High
Fat solubility of residues	Solubility	Likely to be soluble	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	-
	Data type	Based on chemical group	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	-
Density (g ml⁻¹)		1.28	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		5.30 X 10-05	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		1.03 X 10-07	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
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)	2	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	Non-persistent
	DT₅₀ (lab at 20 °C)	2	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data	Non-persistent
	DT₅₀ (field)	58	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data	Moderately persistent
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) on and in plant matrix	Value	1.8	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	-
	Note	Soybean, whole plant, n=1
Aqueous photolysis DT₅₀ (days) at pH 7	Value	0.25	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	Fast
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	14	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	Non-persistent
	Note	-
Water-sediment DT₅₀ (days)		50	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	Moderately fast
Water phase only DT₅₀ (days)		20	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	Slow
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	-	-
	Koc (mL g⁻¹)	-
	Notes and range	-
Freundlich	Kf (mL g⁻¹)	5.4	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes	Slightly mobile
	Kfoc (mL g⁻¹)	892
	1/n	1.00
	Notes and range	Kf range 2.5-7.5 mL g⁻¹, Kfoc range 126-2208 mL g⁻¹, 1/n - no data, Soils=5
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		1.85	Calculated	Transition state
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	6.47 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		Medium	Calculated	-
Potential for loss via drain flow		Slightly mobile	Calculated	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
acifluorfen (Ref: RH 5781)	-	-	-

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		1480	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Rat	Moderate
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)		1418	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Colinus virginianus	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		6	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source	High
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)	> 100	B3 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 3 = Unverified data of known source	Low
	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	-	-	-
	Notes	-
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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		23	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Oncorhynchus mykiss	Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		0.038	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Oncorhynchus mykiss	Moderate
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		30	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Daphnia magna	Moderate
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		0.00018	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Scenedesmus subspicatus	High
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

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)		1480	B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		5000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		7.5	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat as formulation	-
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		List II	-	-
Exposure Routes	Public	-
	Occupational	-
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 No data found A3 A = Chromosome aberration (EFSA database) 3 = Negative ; B3 B = DNA damage/repair (EFSA database) 3 = Negative ; C3 C = Gene mutation (EFSA database) 3 = Negative ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ?Possibly, status not identified XNo, known not to cause a problem No data found Respiratory tract irritant Skin irritant Skin sensitiser No data found ?Possibly, status not identified No data found Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		Possible blood, Kidney and liver toxicant

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	Health: H302
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	fluoroglycofen
French	fluoroglycophène
German	Fluoroglycofen
Danish	fluoroglycofen
Italian	fluoroglicofene
Spanish	fluroglicofen
Greek	-
Polish	fluoroglikofen
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	19/12/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242