Benfuracarb

Benfuracarb	Last updated: 18/12/2020
(Also known as: OK 174; aminofuracarb)

SUMMARY

Benfuracarb is a carbamate insecticide and nematicide that does not have EU regulatory approval for use. It has a low aqueous solubility, is relatively volatile and is not expected to leach to groundwater. It is not persistent in soil or water systems. It has a moderate mammalian toxicity with a low bioaccumulation potential. It is highly toxic to most aquatic organisms, birds and honeybees but slightly less so to earthworms.

GENERAL INFORMATION

Description

An insecticide and nematicide used to control aphids, springtails and other pests usually on beet crops

Example pests controlled

Diamond back moth; Aphids; Cockroaches; Grain beetle; Springtails; Wireworms; Rootworms; Loopers; Borers

Example applications

Sugarbeet; Maize; Potatoes; Rice; Citrus; Ornamentals

Efficacy & activity

Availability status

Unknown

Introduction & key dates

1984, UK, France and Spain

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Belgium

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

Chemical structure

Isomerism

None

Chemical formula

C₂₀H₃₀N₂O₅S

Canonical SMILES

CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

FYZBOYWSHKHDMT-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H30N2O5S/c1-7-25-17(23)11-12-22(14(2)3)28-21(6)19(24)26-16-10-8-9-15-13-20(4,5)27-18(15)16/h8-10,14H,7,11-13H2,1-6H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Carbamate

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier - 1,2-dichloroethane (EDC) - < 4 g kg⁻¹

Substance origin

Synthetic

Mode of action

Systemic, stomach and contact action. Acetylcholinesterase (AChE) inhibitor.

CAS RN

82560-54-1

EC number

CIPAC number

501

US EPA chemical code

123201

PubChem CID

54886

Molecular mass

410.53

PIN (Preferred Identification Name)

ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β-alaninate

IUPAC name

ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β-alaninate

CAS name

2,3-dihydro-2,2-dimethyl-7-benzofuranyl 2-methyl-4-(1-methylethyl)-7-oxo-8-oxa-3-thia-2,4-diazadecanoate

Other status information

Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

None identified

Physical state

Pale yellow viscous oily liquid

Formulations

Property

Value

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

Oncol 10G
Alba
Furacon
Lonco
Stamex

Example products using this active

Nufarm

Formulation and application details

Usually supplied as granules which are applied directly to soil surface at planting

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

8.4

Low

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

1000000

Acetone

1000000

Methanol

1000000

Hexane

1000000

Xylene

Melting point (°C)

Not applicable

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

154.5

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

1.66 X 10⁰⁴

Calculated

Log P

4.22

High

Bulk density (g ml⁻¹)

1.15

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0042

Low volatility

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

2.10 X 10^-04

Non-volatile

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

Maxima 277.5-281. nm = 3360, 290nm = 614, pH has little impact on spectra

Surface tension (mN m⁻¹)

52.4

at 20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.5

Non-persistent

DT₅₀ (lab at 20 °C)

0.42

Non-persistent

DT₅₀ (field)

4.9

Non-persistent

DT₉₀ (lab at 20 °C)

5.23

Non-persistent

DT₉₀ (field)

47.8

DT₅₀ modelling endpoint

Note

EU dossier lab DT₅₀ range 0.23-1.17d, DT₉₀ range 0.85-20.0 days, field studies DT₅₀ range 3-5 days (Japan), DT₉₀ range 4.4-91 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

4.3

Note

Eggplant fruit, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.3

Moderately fast

Note

DT₅₀: 15.6 days irradiated river water, 4.7 days dark river water, 15.3 hrs irradiated pure water and 30.4 hrs dark pure water

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

Value

1.4

Non-persistent

Note

pH sensitive: DT₅₀ 0.5 hr at pH 4, 26.9 days at pH 9

Water-sediment DT₅₀ (days)

0.4

Fast

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

9100

Notes and range

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

0.03

Calculated

Low leachability

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

Value

3.14 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

carbofuran (Ref: OMS 864)

Soil

0.846

Major fraction, Relevant

3-ketocarbofuran

Soil

0.08

Minor fraction, Relevant

3-hydroxycarbofuran

Soil

0.10

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2,2-dimethyl-2,3-dihydro-1-benzofuran-3,7-diol
Note: Rat LD50 oral = 1654 mg/kg

3-hydroxy-carbofuran phenol

Animal; Plant

7-hydroxy-2,2-dimethyl-1-benzofuran-3(2H)-one
Note: Rat LD50 oral > 800 mg/kg

3-keto-carbofuran phenol

2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol

carbofuran-phenol

Sediment;

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

0.44

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

205

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

19.8

Anas platyrhynchos

High

Birds - Short term dietary (LC₅₀/LD₅₀)

195 mg kg feed⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.038

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.01

Daphnia magna

High

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)

0.0041

Chironomus riparius EC₅₀

High

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.001

Chironomus riparius

High

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)

2.2

Raphidocelis subcapitata

Moderate

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)

0.19

High

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

2.1

Moderate

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)

Eisenia foetida corr

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

9.3

LD₅₀
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

9.2

LD₅₀
Typhlodromus pyri protonymph

% 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)

205

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.344

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.01

Dog SF=100

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

0.02

Rat SF=100

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

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

0.01

Dog SF=100

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified for expected pattern of use

Occupational

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

No further information required

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H302, H331, H3361f
Environment: H400, H410

EC Risk Classification

Reproduction risk category 3: R62
T - Toxic: R23
Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S36/37, S45, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 2992

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

benfuracarb

French

benfuracarbe

German

Benfuracarb

Danish

benfuracarb

Italian

benfuracarb

Spanish

benfuracarb

Greek

benfuracarb

Polish

benfurakarb

Swedish

Hungarian

benfurakarb

Dutch

benfuracarb

Record last updated:	18/12/2020
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