Bromopropylate (Ref: GS 19851)	Last updated: 29/10/2024
(Also known as: phenisobromolate; Isopropyl 2,2-bis-(4-bromo-phen-yl)-2-hy-droxy-acetate)

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SUMMARY

Bromopropylate is an acaricide that is mainly used to control mites. It has a low aqueous solubility and is not considered to be highly volatile. It may be persistent in soil and water systems depending on local conditions. Bromopropylate is not expected to leach into groundwater. It tends to have a low to moderate toxicity to fauna and flora but data is scant. It also has a low mammalian toxicity if ingested but little other health related information is available.

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 High alert: Potential for particle bound transport: High Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Low alert Warning: Significant data are missing

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

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
GB LERAP status	No UK approval for use as a pesticide

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	Expired
EU Candidate for substitution (CfS)	Not applicable
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
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

Chemical structure

Isomerism	None
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	-
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 groups	Bridged diphenol acaricide; Bridged diphenol insecticide
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
CLP index number	No data found
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 Class (HRAC MoA class)	Not applicable
Herbicide Resistance Class (WSSA MoA class)	Not applicable
Insecticide Resistance Class (IRAC MoA class)	UN
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	Tetranychus urticae
Physical state	White crystals

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Syngenta AgroCare Chemicals Ciba-Geigy
Example products using this active	Neoron Acarol
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; Chemspider; PubChem. (ChemID ) 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)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	2.51 X 1005	Calculated	-
	Log P	5.4	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source	High
Fat solubility of residues	Solubility	Soluble	A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes	-
	Data type	Regulatory data - observed in metabolism and farm animal feeding studies	A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes	-
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; Chemspider; PubChem. (ChemID ) 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; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source at 25 °C	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
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. Dataset no longer available. 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 (days) on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) 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; these datasets no longer available). Norman Ecotoxicology database. (click here ) 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; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderately fast
Water phase only DT₅₀ (days)		4	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderately fast
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	W3 W = French database provided by ARVALIS-Institut du Végétal. Dataset no longer available. 3 = Unverified data of known source	Non-mobile
	Koc (mL g⁻¹)	6309
	Notes and range	Best available data
Freundlich	Kf (mL g⁻¹)	-	-	-
	Kfoc (mL g⁻¹)	-
	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	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		-	-	-
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		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
4,4-dibromobenzilic acid	-	-	-

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
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	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)		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)		-	-	-
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)	-	-	-
	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 Apis mellifera	Low
	Chronic	-	-	-
	Notes	-
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)		Harmful	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Typhlodromus pyri	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Temperate Freshwater 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
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater 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
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)		-	-	-
Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)		-	-	-
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 Scenedesmus subspicatus	Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

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)		-	-	-
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	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
	Great Britain	GB MRL Register
	Notes	EU expected to amend MRL in early 2023
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 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	Not expected to auto-ignite; Not highly flammable
CLP classification 2013	Health: H315, H319 Environment: H400, H410
WHO Classification	U (Unlikely to present an acute hazard)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	bromopropylate
French	bromopropylate
German	Bromopropylate
Danish	bromopropylat
Italian	bromopropilato
Spanish	bromopropilato
Greek	-
Polish	bromopropylat
Swedish	-
Hungarian	brompropilat
Dutch	-
Norwegian	-

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Record last updated:	29/10/2024
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