Camphechlor (Ref: Hercules 3956)

Camphechlor (Ref: Hercules 3956)	Last updated: 29/08/2024
(Also known as: toxaphene; polychlorocamphene; chlorocamphene; toxafeen; octachlorocamphene)

SUMMARY

Camphechlor is an obsolete insecticide and acaricide. It has a low aqueous solubility, is quite volatile and moderately mobile. Based on its chemical properties, it has a high risk of leaching to groundwater. It is not expected to be persistent in soil but may be persistent in water systems. Camphechlor is highly toxic to mammals and is likely to bioaccumulate. It is highly toxic to birds and most aquatic organisms.

GENERAL INFORMATION

Description

A topically applied insecticide that is now obsolete

Availability status

Considered obsolete but may be available in some countries; Banned in many countries

Introduction & key dates

1947, developed

Examples of veterinary uses

Control of ticks, fleas and mange mites

Examples of species treated

General livestock

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

Isomeric

Chemical formula

C₁₀H₁₀Cl₈

Canonical SMILES

C1C2C(C(C(C1(Cl)Cl)(C2(CCl)C(Cl)Cl)CCl)Cl)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

YNEKMCSWRMRXIR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H10Cl8/c11-2-8(7(15)16)4-1-10(17,18)9(8,3-12)6(14)5(4)13/h4-7H,1-3H2

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Insecticide

Substance groups

Organochloride insecticide; Organochlorine acaricide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

A non-systemic contact and stomach insecticide. It acts on the neurons, causing an imbalance in sodium and potassium ions, similar to that of the cyclodiene insecticides.

Molecular targets

CAS RN

8001-35-2

EC number

232-283-3

CIPAC number

US EPA chemical code

080501

PubChem CID

58167

CLP index number

602-044-00-1

Therapeutic Class

ATCvet Code

None allocated

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

413.96

PIN (Preferred Identification Name)

IUPAC name

2,2,5,6-tetrachloro-1,7-bis(chloromethyl)-7-(dichloromethyl)bicyclo[2.2.1]heptane

CAS name

2,2,5-endo,6-exo,8,8,9,10-Octachlorobornane

Other status information

OSPAR soc; POP - regulated by Stockholm Convention; Severe Marine Pollutant; Rotterdam Convention (Class O) - subject to PIC regulations; PAN Bad Actor

Relevant Environmental Water Quality Standards

Physical state

Yellow to amber waxy solid

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3.0

Low

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

4500000

Benzene

4500000

Carbon tetrachloride

4500000

Xylene

2800000

Kerosene

Melting point (°C)

Range 65-90

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

2.00 X 10⁰³

Calculated

Log P

3.3

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.65

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.67

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

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

6.08 X 10^-01

Moderately 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)

365

Very persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Literature sources highly variable: DT₅₀ 2 months and 14 years; US sources: 9 days (DW3, US3); Field DT₅₀ 9 to 500 days (R3)

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

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

K_d (mL g⁻¹)

Moderately mobile

K_oc (mL g⁻¹)

295

Notes and range

Literature range for log K_oc = 2.47-5.00; Other sources: K_oc 100000 mL g⁻¹ (US2)

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

1.46

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

76000

High 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

strobane (Ref: ENT 19442)

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)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 15

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)

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)

0.144

Apis mellifera

High

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

> 19.1

Apis mellifera

Moderate

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

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)

0.216

Megachile rotundata

High

Mode of exposure

Contact

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

0.0023

Nomia melanderi

High

Mode of exposure

Contact

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)

0.0044

Lepomis macrochirus

High

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

> 0.00005

Ictalurus punctatus

High

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

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

0.0141

Daphnia magna

High

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

> 0.016

Daphnia magna

Moderate

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

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

0.0021

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 (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)

> 0.38

Pseudokirchneriella subcapitata

Moderate

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

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)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

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

Possible risk via food contamination

Occupational

Absorbed by the intact skin and from the gastrointestinal tract

Mammalian dose elimination route and rate

Mainly eliminated in urine and faeces

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

IARC group 2B carcinogen; CLP data - suspected carcinogen; US NTP - suspected carcinogen; OSHA - anticipated human carcinogen; US EPA - probable human carcinogen
Ingestion may be fatal
May cause convulsions
Potential kidney toxicant
May cause allergic bronchopneumonia
Endocrine issues - Increase of estrogen-sensitive cells proliferation

Handling issues

Property

Value and interpretation

General

Corrosive
Not compatible with strongly alkaline pesticides
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301, H312, H315, H335, H351
Environment: H400, H410

WHO Classification

Not classified: Obsolete (Not classified: Obsolete)

UN Number

UN2996

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

camphechlor

French

bamphéchlore

German

Camphechlor

Danish

camphechlor, toxaphen

Italian

camfeclor

Spanish

camfeclor

Greek

Polish

kamfechlor

Swedish

Hungarian

Dutch

toxafeen

Norwegian

Record last updated:	29/08/2024
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