Fluoroglycofen	Last updated: 02/07/2019
(Also known as: fluoroglycofene; benzofluorfen)

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GENERAL INFORMATION

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

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
UK LERAP status	No UK approval for use

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

Also used in

Also used in	South Africa

Chemical structure

Isomerism	-
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 group	Diphenyl ether
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).
CAS RN	77501-60-1
EC number	-
CIPAC number	523
US EPA chemical code	-
PubChem CID	92395
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 Classification (HRAC)	E
Herbicide Resistance Classification (WSSA)	14
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	-
Physical state	Dark amber solid
Related substances & organisms	isoproturon

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Estrad Trenox Duplo Compete Simitar
Example products using this active	Rohm and Haas Dow AgroScience
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 (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 (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 (click here ) 5 = Verified data used for regulatory purposes	High
Bulk density (g ml⁻¹)		1.28	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (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 (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 / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	Non-volatile
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 (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 (click here ) 4 = Verified data	Non-persistent
	DT₅₀ (field)	58	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data	Moderately persistent
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	-
Dissipation rate RL₅₀ on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ 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 (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 (click here ) 5 = Verified data used for regulatory purposes	Non-persistent
	Note	-
Water-sediment DT₅₀ (days)		50	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	Moderately fast
Water phase only DT₅₀ (days)		20	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	Slow

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	5.4	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Slightly mobile
	Kfoc	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		Low	Calculated	-
Potential for loss via drain flow		Slightly mobile	Calculated	-

Key metabolites

Metabolite	Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
acifluorfen (Ref: RH 5781)	Soil	-	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	Low risk	F2 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 2 = Unverified data of unknown source	Low risk
	CT₅₀ (days)	Not available		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		1480	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (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 (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)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		23	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.038	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		30	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes 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)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		0.00018	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Scenedemus subspicatus	High
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
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 (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)	-	-	-
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 pollinators (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other pollinators (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		6	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source	High
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Other soil macro-organisms	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Other arthropod (1)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Other arthropod (2)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-

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 (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)		0.0095	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data UK ACP 1999	-
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	-
European MRLs		EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

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
EC Risk Classification	Not classified: Obsolete
EC Safety Classification	Not classified: Obsolete
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

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

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Record last updated:	02/07/2019
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