Cyclobutrifluram	Last updated: 19/09/2024
(Not known by any other names)

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SUMMARY

Cyclobutrifluram is a multi-use pesticide which is mostly used as a nematicide. It is slightly soluble in water, very soluble in most organic solvents and is non-volatile. It can be persistent in soil systems under certain conditions - it degrades quicker in moist soils than in dry ones. It tends to demonstrate a low toxicity to humans or biodiversity.

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 High alert: Persistent; GUS: High leachability	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Bees acute unknown ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Low alert

GENERAL INFORMATION

Description	A multi-use pesticide that offers control of a broad spectrum of nematode pests and diseases across all major crops
Example pests controlled	Nematodes including Ring, Southern Sting, Root-knot, Stuby, Dagger, Sheath, Spiral and Beet cyst nematodes; Soil-borne diseases, especially Fusarium
Example applications	Soybean; Cotton; Romaine lettuce; Ornamentals; Turf; Cucumber; Tomato; Corn; Sugarbeet; Banana; Pepper; Coffee; Melon; Tobacco
Efficacy & activity	Efficacy as a nematicide established from extensive field trials
Availability status	Current
Introduction & key dates	2103, first patent; 2020, introduction

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Not applicable
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	Not applicable
Date EC 1107/2009 inclusion expires	Not applicable
EU Candidate for substitution (CfS)	Not applicable
Listed in EU database	No
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	Australia; Argentina; Chile; China; Belize; Columbia; El Salvador; Paraguay; South Korea; Vietnam; Zimbabwe; Guatemala

Chemical structure

Isomerism	Isomeric - containing 80–100% of the (1S,2S)-enantiomer and 20–0% of the (1R,2R)-enantiomer
Chemical formula	C₁₇H₁₃Cl₂F₃N₂O
Canonical SMILES	-
Isomeric SMILES	-
International Chemical Identifier key (InChIKey)	GBFKIHJZPMECCF-FZMZJTMJSA-N
International Chemical Identifier (InChI)	InChI=1S/C17H13Cl2F3N2O/c18-9-3-4-10(13(19)8-9)11-5-6-14(11)24-16(25)12-2-1-7-23-15(12)17(20,21)22/h1-4,7-8,11,14H,5-6H2,(H,24,25)/t11-,14-/m0/s1
2D structure diagram/image available?	Yes

General status

Pesticide type	Fungicide, Nematicide
Substance groups	Pyridine fungicide; Amide fungicide; Pyridine nematricide; Amide nematicide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	An SDHI fungicide. Inhibitor of the mitochondrial electron transport chain complex II
CAS RN	1460292-16-3
EC number	856-353-3
CIPAC number	None allocated
US EPA chemical code	126002
PubChem CID	-
Molecular mass	389.2
PIN (Preferred Identification Name)	N-[2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide
IUPAC name	N-[2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide
CAS name	rel-N-[(1R,2R)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)-3-pyridinecarboxamide
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Class (HRAC MoA class)	Not applicable
Herbicide Resistance Class (WSSA MoA class)	Not applicable
Insecticide Resistance Class (IRAC MoA class)	N-3
Fungicide Resistance Class (FRAC MOA class)	C2
Examples of recorded resistance	None identified
Physical state	Solid, off-white coloured, odourless crystalline powder

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Syngenta
Example products using this active	Tymirium Victrato Trefinti Turf nematicide Vaniva
Formulation and application details	Formulated for application as a suspension concentrate via soil treatment or as a seed treatment.

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		19	P4 P = Other non-EU, UK or US Governments and Regulators 4 = Verified data	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		500000	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Acetone	-
		420000	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Methanol	-
		390000	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Ethyl acetate	-
		69000	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Octanol	-
Melting point (°C)		124.6	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.58 X 1003	Calculated	-
	Log P	3.2	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	High
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		1.4	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		6.2 X 10-03	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		7.3 X 10-05	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		Acidic soln: 225nm=12817 Basic soln: 225nm=12970 Neutral soln: 225nm=11792	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	-
Surface tension (mN m⁻¹)		-	-	-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT₅₀ (typical)	23	P4 P = Other non-EU, UK or US Governments and Regulators 4 = Verified data	Non-persistent
	DT₅₀ (lab at 20 °C)	23	P4 P = Other non-EU, UK or US Governments and Regulators 4 = Verified data	Non-persistent
	DT₅₀ (field)	138	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Persistent
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Australian dossier 2024: Lab study: DT₅₀ in moist soil = 14.7 days, in dry soil DT₅₀ 52.8 days. Field studies: DT₅₀ slow under dark aerobic conditions DT₅₀ range 27.1-248 days
Dissipation rate RL₅₀ (days) on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	18	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Slow
	Note	DT₅₀ of 11 to 24 days under summer sunlight
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Stable
	Note	Stable at pH4,7 & 9 at temps up to 70 °C
Water-sediment DT₅₀ (days)		697	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Stable
Water 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)	6.46	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	Moderately mobile
	Kfoc (mL g⁻¹)	333
	1/n	0.87
	Notes and range	Australian dossier: Kf range 3.39-9.53 L/kg, Koc range 210-585 L/kg
pH sensitivity		Weak correlation with OC

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		3.16	Calculated	High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	4.12 X 10-01	Calculated	-
	Note	-
Potential for particle bound transport index		Medium	Calculated	-
Potential for loss via drain flow		Moderately mobile	Calculated	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		1.73	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Calculated using the Atkinson method, 12 hr	Below the level of concern for long-range air transport
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
Ref: CGA177291	Major fraction	0.140	P5
Ref: EXC8199	Major fraction	0.115	P5

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction
Ref: SYN510275	-	Rat; Animal; Plant	-
Ref: SYN549104	-	Plant; Animal	-
Ref: SYN552301	-	Plant	-
Ref: SYN552202	-	Plant	-
Ref: SYN510275	-	Plant	-
Ref: SYN510260	-	Plant	-
trifluoroacetic acid	-	Plant	-

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 5000	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Rat	Low
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)		> 1264	P5 P = Other non-EU, UK or US Governments and Regulators 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)		> 500	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Eisenia andrei	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		212	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Eisenia andrei	Low
Soil micro-organisms		-	-	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Non-target plants		> 900	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Various plants n=10 Seedling emergence, ER₅₀ as g ha⁻¹	-
		> 900	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Various plants n=10 Vegetative vigour, ER₅₀ as g ha⁻¹	-
Honeybees (Apis spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	> 200	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Apis mellifera	Low
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	> 72	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Apis mellifera	Moderate
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	> 30	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Apis mellifera Larvae	Moderate
	Chronic	-	-	-
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)		11.0	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Pimephales promelas	Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.33	P4 P = Other non-EU, UK or US Governments and Regulators 4 = Verified data Cassostrea virginica	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)		9.5	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Raphidocelis subcapitata	Moderate
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)		> 5000	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		-	-	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		0.08	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes Australia	-
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		-	-	-
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		Excretion usually in 72-168 hrs after dosing, Major route is via bile and urine	P5 P = Other non-EU, UK or US Governments and Regulators 5 = Verified data used for regulatory purposes	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor XNo, known not to cause a problem A0 A = Chromosome aberration (EFSA database) 0 = No data ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant XNo, known not to cause a problem No data found XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser No data found XNo, known not to cause a problem XNo, known not to cause a problem Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		No information available

Handling issues

Property	Value and interpretation
General	Not flammable Not explosive Slightly corrosive to some metals
CLP classification 2013	-
WHO Classification	Not listed (Not listed)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	Stable at room temperature >1 yr.

TRANSLATIONS

Language	Name
English	cyclobutrifluram
French	cyclobutrifluram
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	19/09/2024
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