Butafenacil (Ref: CGA 276854)	Last updated: 02/01/2021
(Not known by any other names)

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GENERAL INFORMATION

Description	Used to control annual and perennial broad-leaved weeds in fruit and other crops
Example pests controlled	Annual ryegrass; Capeweed; Clover; Sowthistle; Field beans; Poppies; Prickly lettuce; Wild radish; Rocket; Paradoxa grass; Fathen; Bermudagrass
Example applications	Cotton; Fruit including apples, pears, citrus, plums, apricots, cherries, grapes; Garlic & onions; Non-cropped land; Cereals incuding wheat
Efficacy & activity	-
Availability status	Current
Introduction & key dates	circa 2000

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Not applicable
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	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

Also used in

Also used in	Australia; Argentina; Brazil; Japan; Thailand

Chemical structure

Isomerism	-
Chemical formula	C₂₀H₁₈ClF₃N₂O₆
Canonical SMILES	CC(C)(C(=O)OCC=C)OC(=O)C1=C(C=CC(=C1)N2C(=O)C=C(N(C2=O)C)C(F)(F)F)Cl
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	JEDYYFXHPAIBGR-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C20H18ClF3N2O6/c1-5-8-31-17(29)19(2,3)32-16(28)12-9-11(6-7-13(12)21)26-15(27)10-14(20(22,23)24)25(4)18(26)30/h5-7,9-10H,1,8H2,2-4H3
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
butafenacil	-

General status

Pesticide type	Herbicide
Substance group	Uracil
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Inhibitor of protoporphyrinogen oxidase (PPO), non-selective, contact action absorbed by foliage.
CAS RN	134605-64-4
EC number	-
CIPAC number	None allocated
US EPA chemical code	122004
PubChem CID	11826859
Molecular mass	474.81
PIN (Preferred Identification Name)	2-methyl-1-oxo-1-(prop-2-en-1-yloxy)propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]benzoate
IUPAC name	1-(allyloxycarbonyl)-1-methylethyl 2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate
CAS name	1,1-dimethyl-2-oxo-2-(2-propenyloxy)ethyl 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]benzoate
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	Fine white to grey powder
Related substances & organisms	glyphosate

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Logran B-Power Herbicide Touchdown B-Power
Example products using this active	Syngenta Crop Protection
Formulation and application details	Usually supplied as water dispersible granules

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		10.0	P4 P = Other governments and regulators 4 = Verified data	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		113	P4 P = Other governments and regulators 4 = Verified data	-
Boiling point (°C)		270	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Degradation point (°C)		293	P4 P = Other governments and regulators 4 = Verified data	-
Flashpoint (°C)		Not expected to self ignite; Not highly flammable	P3 P = Other governments and regulators 3 = Unverified data of known source	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.58 X 1003	Calculated	-
	Log P	3.2	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	High
Bulk density (g ml⁻¹)		1.37	P4 P = Other governments and regulators 4 = Verified data	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		7.4 X 10-06	P4 P = Other governments and regulators 4 = Verified data	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		3.5 X 10-07	L3 L = Pesticide manuals and hard copy reference books / other sources 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)	1.5	P4 P = Other governments and regulators 4 = Verified data	Non-persistent
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Australian registration dossier states DT₅₀ 0.2-2.2 days aerobic soils, slower in water logged, anaerobic soils
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	28	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Slow
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	98	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Moderately persistent
	Note	-
Water-sediment DT₅₀ (days)		27	P3 P = Other governments and regulators 3 = Unverified data of known source	Fast
Water phase only DT₅₀ (days)		Slow, DT50 25-30 days	P3 P = Other governments and regulators 3 = Unverified data of known source	Slow, DT50 25-30 days

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	P4 P = Other governments and regulators 4 = Verified data	Moderately mobile
	Koc	365
	Notes and range	Literature values for Koc range 149-581 mL g⁻¹ in four soils
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		0.25	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	5.84 X 10-04	Calculated	-
	Note	-
Potential for particle bound transport index		Low	Calculated	-
Potential for loss via drain flow		Moderately mobile	Calculated	-

Key metabolites

Metabolite	Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
1-carboxy-1-methylethyl 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)benzoate (Ref: CGA 293731)	Soil	-	Not assessed under 91/414 or 1107/2009
Ref: CGA 293730	Soil	0.780	Not assessed under 91/414 or 1107/2009

Other known metabolites

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
-	CGA 293731	Soil (Aerobic)	-	-
-	CGA 293730	Soil (Aerobic)	-	-
-	CGA 380963	Soil (Aerobic)	-	-
- Note: Very persistent	CGA 98166	Water	-	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 5000	P4 P = Other governments and regulators 4 = Verified data 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)		> 2250	P4 P = Other governments and regulators 4 = Verified data Colinus virginianus	Low
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		3.9	P4 P = Other governments and regulators 4 = Verified data Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.011	P3 P = Other governments and regulators 3 = Unverified data of known source Oncorhynchus mykiss survival	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		8.6	P4 P = Other governments and regulators 4 = Verified data Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		> 0.009	P3 P = Other governments and regulators 3 = Unverified data of known source Daphnia magna growth	High
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)		0.0025	P4 P = Other governments and regulators 4 = Verified data 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)	20	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Moderate
	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)		1250	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low
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)		> 5000	P4 P = Other governments and regulators 4 = Verified data Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2000	P4 P = Other governments and regulators 4 = Verified data Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		> 5.1	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
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
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

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 ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data XNo, known not to cause a problem Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant XNo, known not to cause a problem XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser ✓Yes, known to cause a problem ✓Yes, known to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem No data found
General human health issues		Possible liver toxicant

Handling issues

Property	Value and interpretation
General	Not oxidising or explosive IMDG Transport code 9
CLP classification 2013	Health: H373 Environment: H400, H410
EC Risk Classification	None allocated at this time
EC Safety Classification	-
WHO Classification	III (Slightly hazardous)
UN Number	3077
Waste disposal & packaging	Packaging Group III (minor danger)

TRANSLATIONS

Language	Name
English	butafenacil
French	-
German	-
Danish	-
Italian	-
Spanish	butafenacilo
Greek	-
Polish	butafenacyl
Swedish	-
Hungarian	-
Dutch	-

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Record last updated:	02/01/2021
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