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Butroxydim (Ref: ICIA0500)
Last updated: 03/07/2019
(Not known by any other names)

SUMMARY
Butroxydim is an obsolete herbicide without EU regulatory approval for use. It has a low aqueous solubility, is relatively volatile and, based on its chemical properties, is non-mobile and would not be expected to leach to groundwater. It is generally non-persistent in soil systems but may persist in aquatic systems under certain conditions. It is not generally susceptible to hydrolysis. It has a moderate mammalian toxicity and has a high potential to bioaccumulate. It is moderately toxic to most aquatic species, birds and earthworms but relatively non-toxic to honey bees.
GENERAL INFORMATION
Description
Used for the control of Digitaria spp. and other grass species in soya and other broad leaved crops.
Example pests controlled
Annual ryegrass; Barley grass; Wild oats; Brome grass; Velvetgrass; Crabgrass; Barnyard grass; Johnsson grass
Example applications
Soybeans; vegetables including peas, beans, chickpeas, lentils; Linseed; Lucerne; Lupins; Vetches; Cotton; sunflowers
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1995, first sold
UK regulatory status
UK approval status
Not approved
EC Regulation 1107/2009 (repealing 91/414)
EC Directive 91/414 Status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
Approved for use (✓) or known to be used (#) in the following EU-27 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
Chemical structure
Isomerism
Butroxydim is a chiral molecule
Chemical formula
C₂₄H₃₃NO₄
Canonical SMILES
CCCC(=O)C1=C(C(=C(C=C1C)C)C2CC(=O)C(=C(CC)NOCC)C(=O)C2)C
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
LQNKITCRDAZSGT-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C24H33NO4/c1-7-10-19(26)23-15(5)11-14(4)22(16(23)6)17-12-20(27)24(21(28)13-17)18(8-2)25-29-9-3/h11,17,27H,7-10,12-13H2,1-6H3
2D structure diagram/image available?
Yes
General status
Pesticide type
Herbicide
Substance group
Cyclohexanedione
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Selective and systemic. Inhibition of lipid biosynthesis, absorbed by leaves and translocated. Inhibition of acetyl CoA carboxylase (ACCase).
CAS RN
138164-12-2
EC number
414-790-3
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
butroxydim
Molecular mass
399.53
PIN (Preferred Identification Name)
(5E)-5-(3-butanoyl-2,4,6-trimethylphenyl)-2-[(1E)-N-ethoxypropanimidoyl]-3-hydroxycyclohex-2-en-1-one
IUPAC name
(5RS)-5-(3-butyryl-2,4,6-trimethylphenyl)-2-[(EZ)-1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one
CAS name
2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxobutyl)phenyl]-2-cyclohexen-1-one
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
A
Herbicide Resistance Classification (WSSA)
1
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Brachiaria plantaginea
Physical state
Dirty white powdery soild
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Fusion Super WG herbicide
  • Factor
  • Falcon
Example products using this active
  • Crop Care
UK LERAP status
No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details
Usually supplied as wettable granules
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
6.9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Dichloromethane
-
450000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone
-
90000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol
-
30000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane
-
Melting point (°C)
80.0
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
7.94 X 1001 Calculated -
Log P
1.9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low
Bulk density (g ml⁻¹)
1.2
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
4.36
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Weak acid
Vapour pressure at 20 °C
0.001
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C
5.79 X 10-05
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Non-volatile
GUS leaching potential index
1.14 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
1.41 X 10-02 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
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)
9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Best available data
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
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
240
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Persistent
Note
pH sensitive: Stable pH 7 to pH 9, DT₅₀: 10.5 days at pH 5
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Slightly mobile
Koc
635
Notes and range
Literature values range 6-1270 mL g⁻¹
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
Low risk
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Based on LogP < 3
Low risk
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
1635
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Birds - Acute LD₅₀ (mg kg⁻¹)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Anas platyrhynchos
Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
6.9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
3.7
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (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)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.71
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Pseudokirchneriella subcapitata
Moderate
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)
200
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low
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)
1000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Eisenia foetida
Moderate
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)
1635
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
2.99
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)
0.025
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
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
- - -
Exposure Routes
Public
-
Occupational
-
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
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
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
XNo, known not to cause a problem
Yes, known to cause a problem
XNo, known not to cause a problem
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
No further information available
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H302, H315, H361fd
Environment: H400, H410
EC Risk Classification
Reproduction risk category 3: R62, R63
Xn - Harmful: R22
Xi - Irritant: R38
N - Dangerous for the environment: R50, R53
EC Safety Classification
S2, S22, S36/37, S60, S61
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
butroxydim
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
butroksydym
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 03/07/2019
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