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Butafenacil (Ref: CGA 276854)
(Not known by any other names)
SUMMARY
Butafenacil is a herbicide used to control annual and perennial broad-leaved weeds. Iit has a low aqueous solubility and a low volatility. It is not usually persistant in soil systems but may be moderately persistent in aquatic systems, depending on local conditions. It is moderraely toxic to honeybees and most aquatic species but less so to birds and earthworms. It has a low oral mammalian toxicity and is an irritant,
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
Moderate alert:
Drainflow: Moderately mobile
Warning:
Significant data are missing
Ecotoxicity
High alert:
Fish chronic ecotoxicity: High; Daphnia chronic ecotoxicity: High
Human health
Low alert
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
                 
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; Brazil; Japan; Thailand
Chemical structure
Isomerism
None
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
-
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 groups
Uracil herbicide; Phenyluracil herbicide
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
603-837-4
CIPAC number
None allocated
US EPA chemical code
122004
PubChem CID
11826859
CLP index number
No data found
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
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Syngenta Crop Protection
Example products using this active
  • Logran B-Power Herbicide
  • Touchdown B-Power
  • Inspire EC
Formulation and application details
Usually supplied as water dispersible granules and emulsifiable concentrates
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 non-EU, UK or US Governments and Regulators
4 = Verified data
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
113
P4 P = Other non-EU, UK or US 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 non-EU, UK or US Governments and Regulators
4 = Verified data
 -
Flashpoint (°C)
- - -
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
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.37
P4 P = Other non-EU, UK or US 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 non-EU, UK or US 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 non-EU, UK or US 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 non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
 Fast
Water phase only DT₅₀ (days)
Slow, DT50 25-30 days
P3 P = Other non-EU, UK or US 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 non-EU, UK or US 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 -
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
1-carboxy-1-methylethyl 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)benzoate (Ref: CGA 293731)
- - -
1-carboxy-1-methylethyl 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl] benzoate (Ref: CGA 293730)
Major fraction 0.780 -
Ref: CGA 380963
- - Aerobic
Known groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
-
Note: Very persistent		 CGA 98166 Water - -
Ref: 1165 CGA 293730 Plant - -
- CGA 380963 - - -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
P4 P = Other non-EU, UK or US 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 non-EU, UK or US 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)
- - -
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)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
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)
- - -
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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
3.9
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Oncorhynchus mykiss		 Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.011
P3 P = Other non-EU, UK or US 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 non-EU, UK or US Governments and Regulators
4 = Verified data
Daphnia magna		 Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
> 0.009
P3 P = Other non-EU, UK or US 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)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.0025
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Scenedesmus subspicatus		 High
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
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 non-EU, UK or US Governments and Regulators
4 = Verified data
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
P4 P = Other non-EU, UK or US 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 
Great Britain
GB MRL Register 
Notes
-
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Mammalian dose elimination route and rate
- - -
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 Hazard Class 9
Not expected to autoignite; Not highly flammable
CLP classification 2013
Health: H373
Environment: H400, H410
WHO Classification
III (Slightly hazardous)
UN Number
UN3077
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
butafenacil
French
-
German
-
Danish
-
Italian
-
Spanish
butafenacilo
Greek
-
Polish
butafenacyl
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
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