Bendiocarb (Ref: NC 6897)

Bendiocarb (Ref: NC 6897)	Last updated: 22/08/2024
(Also known as: bendiocarbe; bencarbate)

SUMMARY

Bendiocarb is a carbamate insecticide and veterinary treatment. It has a moderate aqueous solubility, moderate volatility, is moderately mobile but, based on its chemical properties, would not be expected to leach to groundwater. It is highly toxic to mammals but tends not to bioaccumulate. It has a moderate to high toxicity for most aquatic organisms. It is highly toxic to birds and honey so but slightly less to earthworms.

GENERAL INFORMATION

Description

A carbamate insecticide with a wide range of uses including veterinary applications but now largely obsolete

Availability status

Current

Introduction & key dates

1971, introduced

Examples of veterinary uses

Once used to control ectoparasites

Examples of species treated

Domestic pets including dogs

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

None

Chemical formula

C₁₁H₁₃NO₄

Canonical SMILES

CC1(OC2=C(O1)C(=CC=C2)OC(=O)NC)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

XEGGRYVFLWGFHI-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H13NO4/c1-11(2)15-8-6-4-5-7(9(8)16-11)14-10(13)12-3/h4-6H,1-3H3,(H,12,13)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
bendiocarb	-

General status

Veterinary substance type

Antiparasitic

Substance groups

Carbamate insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Systemic, with contact and stomach action resulting in rapid knock-down. Acetylcholinesterase (AChE) inhibitor.

Molecular targets

[Cholinesterase, Inhibitor]

CAS RN

22781-23-3

EC number

245-216-8

CIPAC number

232

US EPA chemical code

105201

PubChem CID

2314

CLP index number

006-046-00-8

Therapeutic Class

Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents

ATCvet Code

QP53AE03

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

223.23

PIN (Preferred Identification Name)

2,2-dimethyl-2H-1,3-benzodioxol-4-yl methylcarbamate

IUPAC name

2,2-dimethyl-1,3-benzodioxol-4-yl methylcarbamate

CAS name

2,2-dimethyl-1,3-benzodioxol-4-yl methylcarbamate

Other status information

Marine Pollutant; PAN Bad Actor Chemical

Relevant Environmental Water Quality Standards

Physical state

White odoureless crystals

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Parasitex Insecticidal Collar

Virbac S.A.

Not licensed

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

280

Moderate

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

250

Dichlorobenzene

175000

Acetone

40000

Ethanol

225

n-Hexane

Melting point (°C)

126.7

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

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

5.01 X 10⁰¹

Calculated

Log P

1.7

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.29

Dissociation constant pKa) at 25 °C

8.8

Very weak acid

Vapour pressure at 20 °C (mPa)

4.6

Low volatility. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

4.00 X 10^-03

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)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

3.5

Non-persistent

DT₅₀ (lab at 20 °C)

5.0

Non-persistent

DT₅₀ (field)

3.5

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Literature values vary from a few days to a few weeks depending on soil type

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Non-persistent

Note

Hydrolysed rapidly in alkali media, slows under acid and neutral conditions

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

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

K_d (mL g⁻¹)

Moderately mobile

K_oc (mL g⁻¹)

385

Notes and range

Other sources K_oc 570 mL g⁻¹ (DW3)

Freundlich

K_f (mL g⁻¹)

K_foc (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

0.77

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

64.8

Lepomis macrochirus

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

2,2-dimethyl-1,3-benzodioxol-4-ol (Ref: NC 7312)

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)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.75

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 3.1

Anas platyrhynchos

High

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

188

Eisenia foetida

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)

0.43

Apis mellifera

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.52

Apis mellifera

High

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

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)

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)

> 1.55

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

7.60

Danio rerio

Moderate

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

0.03

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.00074

Daphnia magna

High

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.006

Americamysis bahia

High

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)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 1.71

Unknown species

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

0.32

Unknown species

Moderate

Mesocosm study data

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)

Rat

High

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

566

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.55

Rat

Other Mammal toxicity endpoints

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

0.004

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

Occupational

Mammalian dose elimination route and rate

The compound was rapidly and extensively absorbed and completely metabolised following oral administration.

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause hepatic and renal diseases
May cause respiratory problems
Endocrine issues - weak estrogen effect

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 6,1

CLP classification 2013

Health: H301, H331, H312
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2757

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bendiocarb

French

bendiocarbe

German

Bendiocarb

Danish

bendiocarb

Italian

bendiocarb

Spanish

bendiocarb

Greek

bendiocarb

Polish

bendiokarb

Swedish

Hungarian

Dutch

bendiocarb

Norwegian

Record last updated:	22/08/2024
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