Barban (Ref: A-980)

Barban (Ref: A-980)	Last updated: 01/09/2023
(Also known as: barbamate; carbyne; carbine; CBN; chlorinate)

SUMMARY

Barban is an obsolete post-emergence carbonate herbicide. It has a low aqueous solubility, is volatile and would not normally be expected to leach to groundwater. It is not persistent in soiI systems and is unlikely to be persistent in water systems. It has a moderate mammalian toxicity with a low potential for bioaccumulation. There are gaps in biodiversity toxicity data but it is reported to be moderately toxic to most aquatic species.

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 Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate Warning: Significant data are missing	Human health Moderate alert: Mammals acute toxicity: Moderate Warning: Significant data are missing

GENERAL INFORMATION

Description

An obsolete, a post-emergent, selective herbicide for control of wild oats and other grasses

Example pests controlled

Wild oats; Canary grass; Italian ryegrass; Blackgrass

Example applications

Cereals, particular barley, wheat; Sugarbeet; Beans & peas; Flax; Lentils; Beet crops including mangolds; Some soft fruit

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

1958, 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

Chemical structure

Isomerism

None

Chemical formula

C₁₁H₉Cl₂NO₂

Canonical SMILES

C1=CC(=CC(=C1)Cl)NC(=O)OCC#CCCl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

MCOQHIWZJUDQIC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H9Cl2NO2/c12-6-1-2-7-16-11(15)14-10-5-3-4-9(13)8-10/h3-5,8H,6-7H2,(H,14,15)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Carbamate ester herbicide; Carbanilate herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Herbicidal action is due to anti-mitotic effects, reducing plant cellular division and so retarding shoot growth. Inhibition of microtubule organisation.

CAS RN

101-27-9

EC number

202-930-4

CIPAC number

134

US EPA chemical code

017601

PubChem CID

7551

CLP index number

006-020-00-6

Molecular mass

258.10

PIN (Preferred Identification Name)

4-chlorobut-2-yn-1-yl (3-chlorophenyl)carbamate

IUPAC name

4-chlorobut-2-ynyl 3-chlorocarbanilate

CAS name

4-chloro-2-butynyl (3-chlorophenyl)carbamate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Solid

Formulations

Property

Value

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

No longer manufactured

Example products using this active

Neoban
Fisons B25
Carbyne
Dualweed

Formulation and application details

No longer available

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

11.0

Low

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

327000

Benzene

113000

n-Butylbenzene

257000

Toluene

279000

Xylene

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

224

Flashpoint (°C)

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

2.57 X 10⁰³

Calculated

Log P

3.41

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.39

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.05

Low volatility

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

1.17 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)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

9.5

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Field studies literature values DT₅₀ range 4-15 days; Other general literature 1-60 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) 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

0.05

Non-persistent

Note

pH sensitive: 1.1 hours at pH7, 7 mins at pH8

Water-sediment DT₅₀ (days)

Water 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)

Slightly mobile

K_oc (mL g⁻¹)

1000

Notes and range

Other sources: K_oc 1200 mL g⁻¹ estimate (CA2)

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

0.98

Calculated

Low leachability

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

Value

1.28 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

2.2

Low potential

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

527

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)

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)

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)

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)

0.53

Cyprinus carpio

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)

0.30

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 - Acute 7 day EC₅₀, biomass (mg l⁻¹)

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

10.0

Chlorella pyrenoidosa

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)

527

Rat

Moderate

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

1600

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

27.4

Rabbit 4 hr

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 population exposure should be low or non-existent since barban is no longer produced or used

Occupational

Occupational exposure should be low or non-existent since barban is no longer produced or used

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

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

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

May cause contact dermatitis
Potential immunosuppressant

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 6,1

CLP classification 2013

Health: H302, H317
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2757

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

barban

French

barbane

German

Barban

Danish

Italian

Spanish

Barban

Greek

Polish

barban

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	01/09/2023
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