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Bromopropylate (Ref: GS 19851)
Last updated: 05/01/2021
(Also known as: phenisobromolate; Isopropyl 2,2-bis-(4-bromo-phen-yl)-2-hy-droxy-acetate)

GENERAL INFORMATION
Description
A bridged diphenyl acaricide used to control mites on fruit and other crops
Example pests controlled
European red mite; Two-spotted mite; Carmine mite; Apple rust mite; Bryobia mite
Example applications
Fruit crops including citrus, grapes, strawberries and other berries; Cotton; Hops; Sugarbeet; Sugarcane; Tea; Ornamentals; Some vegetables
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1967, first reported
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
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
-
Date EC 1107/2009 inclusion expires
Expired
EU Candidate for substitution (CfS)
-
Listed in EU database
Yes
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
Chemical structure
Isomerism
-
Chemical formula
C₁₇H₁₆Br₂O₃
Canonical SMILES
CC(C)OC(=O)C(C1=CC=C(C=C1)Br)(C2=CC=C(C=C2)Br)O
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
FOANIXZHAMJWOI-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C17H16Br2O3/c1-11(2)22-16(20)17(21,12-3-7-14(18)8-4-12)13-5-9-15(19)10-6-13/h3-11,21H,1-2H3
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
bromopropylate -
General status
Pesticide type
Acaricide
Substance group
Benzilate
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non systemic with contact action and residual activity
CAS RN
18181-80-1
EC number
242-070-7
CIPAC number
503
US EPA chemical code
028802
PubChem CID
28936
Molecular mass
428.1
PIN (Preferred Identification Name)
propan-2-yl bis(4-bromophenyl)hydroxyacetate
IUPAC name
isopropyl 4,4'-dibromobenzilate
CAS name
1-methylethyl 4-bromo-α-(4-bromophenyl)-α-hydroxybenzeneacetate
Other status information
Slightly phytoxic to some varieties of apple, plum and ornamentals
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
UN - uncertain mode of action
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Tetranychus urticae
Physical state
White crystals
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Neoron
  • Acarol
Example products using this active
  • Syngenta
  • AgroCare Chemicals
  • Ciba-Geigy
Formulation and application details
Usually supplied as an emulsifiable concentrate.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.1
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
at 25 °C
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
850000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone
-
970000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Dichloromethane
-
750000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Benzene
-
530000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene
-
Melting point (°C)
77
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Boiling point (°C)
Decomposes before boiling
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
Not expected to self ignite; Not highly flammable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Octanol-water partition coefficient at pH 7, 20 °C
P
2.51 X 1005 Calculated -
Log P
5.4
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
High
Bulk density (g ml⁻¹)
1.59
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
0.011
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
at 25 °C
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
4.70 X 10-02
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
at 25 °C
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)
59
W4 W = French database provided by ARVALIS-Institut du Végétal
4 = Verified data
Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Field and lab studies DT₅₀ range 40-70 days; Other sources DT₅₀ 4-13 weeks (R4)
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
6.2
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature RL₅₀ range 2.0-15.8 days, 4 field and undercover grown crops, various matrices, n=5
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
118
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
Persistent
Note
DT₅₀: 34 days at pH 9 (L3)
Water-sediment DT₅₀ (days)
63
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
Moderately fast
Water phase only DT₅₀ (days)
4
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
Moderately fast
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
W3 W = French database provided by ARVALIS-Institut du Végétal
3 = Unverified data of known source
Non-mobile
Koc
6309
Notes and range
Best available data
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
0.35 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
8.33 X 10-03 Calculated -
Note
-
Potential for particle bound transport index
High Calculated -
Potential for loss via drain flow
Non-mobile Calculated -
Key metabolites
Metabolite
Formation medium
Estimated maximum occurrence fraction
1107/2009 relevancy
4,4-dibromobenzilic acid
Soil - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
1050
N3 N = Various trusts, NGOs & charities data
3 = Unverified data of known source
Whole fish
Threshold for concern
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
L3 L = Pesticide manuals and hard copy reference books / other sources
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)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Coturnix japonica
Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.35
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)
0.17
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)
52
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Scenedemus subspicatus
Low
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)
183
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low
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
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
Harmful
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Typhlodromus pyri
-
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
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
4000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
4.0
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)
0.03
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
JMPR 1993
-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.2
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
UK ACP 1999
-
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
General public exposure should be low since substance is largely obsolete
Occupational
Occupational exposure should be low since substance is largely obsolete
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
XNo, known not to cause a problem
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
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
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: H315, H319
Environment: H400, H410
EC Risk Classification
Xi - Irritant: R38
EC Safety Classification
None
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
bromopropylate
French
bromopropylate
German
Bromopropylate
Danish
bromopropylat
Italian
bromopropilato
Spanish
bromopropilato
Greek
-
Polish
bromopropylat
Swedish
-
Hungarian
brompropilat
Dutch
-

Record last updated: 05/01/2021
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