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Bromobutide (Ref: S 4347 )
Last updated: 04/01/2021
(Also known as: S-47)

GENERAL INFORMATION
Description
A novel selective, post emeregnce herbicide that is currently used to control perennial weeds in paddy fields
Example pests controlled
Cockspur (Echinochloa oryzicola); False pickerelweed (Monochoria vaginals); Rotala indica; Scirpus juncoides
Example applications
Paddy rice
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1981, first reported
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
Japan
Chemical structure
Isomerism
A chiral molecule. The technical material is an isomeric mixture.
Chemical formula
C₁₅H₂₂BrNO
Canonical SMILES
CC(C)(C)C(C(=O)NC(C)(C)C1=CC=CC=C1)Br
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
WZDDLAZXUYIVMU-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C15H22BrNO/c1-14(2,3)12(16)13(18)17-15(4,5)11-9-7-6-8-10-11/h6-10,12H,1-5H3,(H,17,18)
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
bromobutide -
General status
Pesticide type
Herbicide
Substance group
Amide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Inhibition of 4-hydroxyphenyl-pyruvate dioxygenase, bleaching
CAS RN
74712-19-9
EC number
-
CIPAC number
-
US EPA chemical code
-
PubChem CID
53079
Molecular mass
312.25
PIN (Preferred Identification Name)
rac-(2R)-2-bromo-3,3-dimethyl-N-(2-phenylpropan-2-yl)butanamide
IUPAC name
(RS)-2-bromo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)butyramide
CAS name
2-bromo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)butanamide
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Z
Herbicide Resistance Classification (WSSA)
0
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
-
Physical state
Colourless to yellow crystals
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Sumiherb
  • Lyton
Example products using this active
  • Sumitomo
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
3.54
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
at 25 °C
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
4700
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Xylene
-
35000
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Methanol
-
500
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Hexane
-
Melting point (°C)
-112
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
-
Boiling point (°C)
101.4
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
23
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
(closed cup)
-
Octanol-water partition coefficient at pH 7, 20 °C
P
3.02 X 1003 Calculated -
Log P
3.48
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
High
Bulk density (g ml⁻¹)
1.276
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
74.0
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Highly volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
6.53
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Moderately 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)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
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
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
- - -
Koc
-
Notes and range
-
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
- - -
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated - -
Note
-
Potential for particle bound transport index
- - -
Potential for loss via drain flow
- - -
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
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
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)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 10.0
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Cyprinus carpio
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
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)
- - -
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)
- - -
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)
- - -
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
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Rat
-
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)
- - -
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
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
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
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
May cause damage to lungs and mucous membranes
Handling issues
Property
Value and interpretation
General
Flammable
CLP classification 2013
-
EC Risk Classification
Xi - Irritant: R36/38
H - Handling risks: R10
EC Safety Classification
-
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
1126
Waste disposal & packaging
Packaging Group II (moderate danger)
TRANSLATIONS
Language
Name
English
bromobutide
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 04/01/2021
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