flurtamone (Ref: RPA 590515) ** SX 1802 ** RE 40885 ** Translations

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SUMMARY

Flurtamone is an approved herbicide under EU regulations and used to control broad-leaved weeds and grasses. It has a low aqueous solubility, low volatility and, based on its chemical properties, is not expected to leach to groundwater. It is not normally persistent in soil or water-sediment systems. It has a low mammalian toxicity and no serious health risks have been identified from the literature. It has a low to moderate toxicity to most terrestrial and aquatic species, with the exception of aquatic plants for which toxicity is high.

GENERAL INFORMATION
for flurtamone

Description: A pre-emergence or post-emergence herbicide used pre-planting and soil incorporated to control broad-leaved and some grasses

Example pests controlled: Broad-leaved weeds, Grasses

Example applications: Cereals including barley, wheat, oats, rye; Sunflower; Cotton; Peas

Efficacy & activity: Many products using flurtamone have been in use in the EU more many years with efficiacy proven in the field and under test conditions.

Availability status: Current

Introduction & key dates: circa 1990

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

Status	Approved
Dossier rapporteur/co-rapporteur	Czech Republic/Ireland
Date inclusion expires	31/10/2019
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

Chemical structure:

Isomerism	A chiral molecule existing in the R- and S-forms
Chemical formula	C18H14F3NO2
Canonical SMILES	CNC1=C(C(=O)C(O1)C2=CC=CC=C2)C3=CC(=CC=C3)C(F)(F)F
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	NYRMIJKDBAQCHC-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C18H14F3NO2/c1-22-17-14(12-8-5-9-13(10-12)18(19,20)21)15(23)16(24-17)11-6-3-2-4-7-11/h2-10,16,22H,1H3
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams:

Common Name	Relationship	Link
Flurtamone	Unstated isomer

General status:

Pesticide type	Herbicide
Substance group	Pyridazinone
Minimum active substance purity	982 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Bleaching: inhibition of carotenoid biosynthesis.
CAS RN	96525-23-4
EC number	None allocated
CIPAC number	569
US EPA chemical code	-
PubChem CID	91755
Molecular mass (g mol-1)	333.30
PIN (Preferred Identification Name)	-
IUPAC name	(RS)-5-methylamino-2-phenyl-4-(α,α,α-trifluoro-m-tolyl)furan-3(2H)-one
CAS name	5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3(2H)-furanone
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	F1
Herbicide Resistance Classification (WSSA)	12
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	-
Physical state	Pale yellow powder
Related substances & organisms	diflufenican

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Bayer CropScience Aventis Rhone-Poulenc
Example products using this active	Bacara Graduate Ingot Chevron Dolmen
UK LERAP status	None
Formulation and application details	Usually supplied as a soluble concentrate applied as an aqueous sloution using standard spraying equipment. at 0.5 L product in 200-400 L water / ha.

ENVIRONMENTAL FATE
for flurtamone

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		10.7	A5 - @pH5	Low
Solubility - In organic solvents at 20oC (mg l-1)		350000	A5 - Acetone	-
		199000	A5 - Methanol	-
		18	A5 - Hexane	-
		133000	A5 - Ethyl acetate	-
Melting point (oC)		148.5	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		190	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.74 X 1003	Calculated	-
	Log P	3.24	A5	High
Bulk density (g ml-1)/Specific gravity		1.38	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		7.0 X 10-07	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		2.03 X 10-08	A5	Non-volatile
GUS leaching potential index		1.64	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	2.74 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 276.2nm=28128; [Acidic solution: 272.6nm=23912; [Basic solution: 215.6nm=17530, 272.6nm=18755	A5	-
Surface tension (mN m-1)		72.1	A5 at 20 degC, 99.1%	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		Not considered to be readily biodegradable
Soil degradation (days) (aerobic)	DT50 (typical)	10.7	A5	Non-persistent
	DT50 (lab at 20oC)	10.7	A5	Non-persistent
	DT50 (field)	35.8	A5	Moderately persistent
	DT90 (lab at 20oC)	250	A4	-
	DT90 (field)	184	A5	-
	DT50 modelling endpoint	-	-	-
	Note	EU 2017 dossier lab studies DT50 range 9.1-11.7 days, DT90 range 30.2-39.9 days, Soils=4; field studies DT50 range 46-65 days, DT90 range 152-216 days
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	1.0	A5	Moderately fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5 to pH 9 at 25 degC
Water-sediment DT50 (days)		82.4	A5	Moderately fast
Water phase only DT50 (days)		16.0	A5	Slow

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	6.95	A4	Moderately mobile
	Kfoc	257.3
	1/n	0.876
	Notes and range	EU 2016 dossier Kf range 4.47-10.62 mL/g, Kfoc range 225-288 mL/g, 1/n range 0.87-0.86, Soils=5
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
trifluoroethanoic acid		Soil	0.055	Minor fraction, Relevant
3-trifluoromethylbenzoic acid (Ref: RE-54488)		Soil	0.247	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
benzoic acid (Ref: ) Note: Major fraction, Relevant	-	Soil	-	-

ECOTOXICOLOGY
for flurtamone

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	27.5	A5 Whole fish	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	6.3	B5 Rat	High
	(ppm diet)	100		-
Birds - Acute LD50 (mg kg-1)		> 2530	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 6000 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		7	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.63	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		13	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.071	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)		0.0099	A5 Lemna gibba	High
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.02	A4 Raphidocelis subcapitata, 72 hour	Moderate
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)	> 304	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 1800	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	33.8	Mortality Dose: 0.25 kg ha-1 A5 Aphidius rhopalosiphi, adult	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	92.1	Mortality Dose: 0.25 kg ha-1 A5 Typhlodromus pyri	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: <5% slight stimulation of soil respiration	A3 Dose: Not stated	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for flurtamone

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 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 2.2	A5 Rat 4hr (whole body)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.03	A3	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A3	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		0.19	A3 Rat, SF=300	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.02	A3 Dog, 1 year, SF=100	-
Dermal penetration studies (%)		0.3-8.0%	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks for bystanders identified
	Occupational	No unacceptable risks to operators or workers identified
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		Possible kidney, liver and spleen 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 IMDG Transport Code is usually 9
CLP classification 2013		Environment: H400, H410
EC Risk Classification		N - Dangerous for the environment: R50, R53
EC Safety Classification		S61, S60
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		No consensus across products or no products available	-	-
UN Number		Usually 3077
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for flurtamone

Language	Name
English	flurtamone
French	flurtamone
German	Flurtamone
Danish	flurtamon
Italian	flurtamone
Spanish	flurtamone
Greek	flurtamone
Slovenian	flurtamon
Polish	flurtamon
Swedish	flurtamon
Hungarian	-
Dutch	flurtamone

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Record last updated: Monday 05 November 2018
Contact: aeru@herts.ac.uk