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)

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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	tetradifon

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
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 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	-

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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