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

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
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
-

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