Denatonium benzoate (Ref: ASU 90 820 P)

Denatonium benzoate (Ref: ASU 90 820 P)	Last updated: 12/01/2021
(Also known as: lidocaine benzyl benzoate; denathonium benzoate)

SUMMARY

Denatonium benzoate is a long-lasting deer repellent that is approved for use in the EU. It has a high aqueous solubility and, based on its chemical properties, appears to have a tendency to leach to groundwater. However, its usage pattern would normally significantly reduce this risk. It is moderately persistent in soils and may persist in water under certain circumstances. Denatonium benzoate is moderately toxic to mammals and has a high tendency to bioaccumulate. It is also an irritant. It is moderately toxic to birds but less so to fish and aquatic invertebrates.

GENERAL INFORMATION

Description

A repellent used to deter deer damaging deciduous and conifer trees in forests

Example pests controlled

Deer; Other large mammals

Example applications

Forests; Woodland

Efficacy & activity

Availability status

Current

Introduction & key dates

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

Approved

Dossier rapporteur/co-rapporteur

Italy/Poland

Date EC 1107/2009 inclusion expires

31/08/2022

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

Australia

Chemical structure

Isomerism

Chemical formula

C₂₈H₃₄N₂O₃

Canonical SMILES

CC[N+](CC)(CC1=CC=CC=C1)CC(=O)NC2=C(C=CC=C2C)C.C1=CC=C(C=C1)C(=O)[O-]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

VWTINHYPRWEBQY-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H28N2O.C7H6O2/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;8-7(9)6-4-2-1-3-5-6/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9)

2D structure diagram/image available?

Yes

General status

Pesticide type

Repellent

Substance group

Unclassified

Minimum active substance purity

995 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Long lasting, repellent action caused by a combination of optical and bitter taste effects. Deer do not associate the white colour with food.

CAS RN

3734-33-6

EC number

2230-95-2

CIPAC number

845

US EPA chemical code

009106

PubChem CID

19518

Molecular mass

446.59

PIN (Preferred Identification Name)

IUPAC name

benzyl diethyl ((2,6-xylylcarbamoyl)methyl) ammonium benzoate

CAS name

N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme-thanaminium benzoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White granular powder

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Arbinol B
Bitrex
Anispray
Toxishield

Example products using this active

Formulation and application details

Often used as a liquid formulation brushed on to tree bark or as a plant dip. 0.2-0.7 g per 1000 trees, applied once each season

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

42400

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

140000

Acetone

4900

Benzene

355000

Ethanol

2500

Ethyl acetate

Melting point (°C)

164.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

301

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

1.51 X 10⁰⁰

Calculated

Log P

0.18

Low

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

4.05

Vapour pressure at 20 °C (mPa)

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

50.7

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

One literature study reports DT₅₀ as approx. 45 days, one other reports slow degradation.

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

Stable

Note

Stable at all relevant pH's

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Very mobile

K_oc

0.9

Notes and range

One study

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

6.69

Calculated

High leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

7.33 X 10⁰⁰

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Very mobile

Calculated

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

841

Rat

Moderate

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)

196

Colinus virginianus

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)

> 1000

Salmo gairdneri

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 500

Daphnia magna

Low

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

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)

841

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.2

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

None allocated

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

None allocated

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders for the proposed patterns of use

Occupational

Negligible risk to operators for the proposed patterns of use

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

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Toxic on ingestion - may cause diarrhea, decreased respiratory rate and salivation

Handling issues

Property

Value and interpretation

General

No explosive or oxidising

CLP classification 2013

Health: H302, H315, H318, H330, H332
Environment: H412

EC Risk Classification

T+ - Very Toxic: R26
Xn - Harmful: R22, R41
N- Dangerous for the environment: R51, R53

EC Safety Classification

S2, S13, S26, S39, S45, S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

denatonium benzoate

French

benzoate de denatonium

German

Denatoniumbenzoat

Danish

Italian

Spanish

benzoato de denatonio

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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