Quinoclamine

Quinoclamine	Last updated: 08/03/2021
(Also known as: CAN; ACNQ)

GENERAL INFORMATION

Description

A selective herbicide and algicide used for post-emergence control of a range of weeds

Example pests controlled

Mosses; Liverworts; Duckweed; Algae

Example applications

Amenity turf; Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

1972

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Sweden/Germany

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
		✓	✓

Also used in

Chemical structure

Isomerism

Chemical formula

C₁₀H₆CINO₂

Canonical SMILES

C1=CC=C2C(=C1)C(=O)C(=C(C2=O)Cl)N

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OBLNWSCLAYSJJR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H6ClNO2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H,12H2

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
quinoclamine	-

General status

Pesticide type

Herbicide, Algicide

Substance group

Unclassified

Minimum active substance purity

965 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, inhibits photosynthesis

CAS RN

2797-51-5

EC number

220-529-2

CIPAC number

648

US EPA chemical code

206501

PubChem CID

17748

Molecular mass

207.61

PIN (Preferred Identification Name)

2-amino-3-chloronaphthalene-1,4-dione

IUPAC name

2-amino-3-chloro-1,4-naphthoquinone

CAS name

2-amino-3-chloro-1,4-naphthalenedione

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Yellow crystals

Formulations

Property

Value

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

Mogeton

Example products using this active

Certis
Acros Organics

Formulation and application details

Often supplied as a wettable powder that is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

20.7

Low

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

10000

Ethyl acetate

10000

Methanol

10000

p-Xylene

10000

n-Heptane

Melting point (°C)

201

Boiling point (°C)

348

Degradation point (°C)

348

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.80 X 10⁰¹

Calculated

Log P

1.58

Low

Bulk density (g ml⁻¹)

1.55

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

7.00 X 10^-03

Low volatility

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

3.05 X 10^-03

Non-volatile

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

219nm = 14100, 266nm = 21500, 339nm = 2410, 460nm = 2570

Surface tension (mN m⁻¹)

72.1

at 20°C 99%

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)

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

103

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Lab studies DT₅₀ range 20-39 days, DT₉₀ range 68-130 days; field studies DT₅₀ range 11-29 days Germany, DT₉₀ range 36-98 days

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

2.2

Moderately fast

Note

Other data: DT₅₀ 60 days in distilled water, 31 days natural water (L3)

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

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

4.6

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

9.1

Slightly mobile

K_oc

1161

Notes and range

EU dossier K_d range 4.2-14 mL g⁻¹, K_oc range 712-1609 mL g⁻¹, Soils=2

Freundlich

K_f

11.7

Slightly mobile

K_foc

896

¹/_n

0.77

Notes and range

EU dossier K_f range 3.72-26, K_foc range 552-1264 mL g⁻¹ ¹/_n range 0.69-0.84, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.41

Calculated

Low leachability

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

Value

3.12 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2-amino-1,4-naphtoquinone

Water/sediment

0.18 (whole system)

2-hydroxy-1,4-naphtoquinone

Soil (Aerobic)

1,4-dihydroxynaphtoquinone

DHN

Soil (Aerobic)

HCN

Soil (Anaerobic)

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)

> 200

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)

> 2000

Unknown species

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

394 mg kg bw⁻¹ day⁻¹

Unknown species

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.063

Cyprinidae

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.02

Oncorhynchus mykiss

Moderate

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

2.15

Daphnia magna

Moderate

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

0.0021

Daphnia magna

High

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)

0.063

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.1

Unknown species

Moderate

Non-target plants

870

Brassica napus
Vegetative vigour, ER₅₀
as g ha⁻¹

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

0.5

Unknown species

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)

> 0.75

High

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

> 100

Low

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)

> 125

Eisenia foetida

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

3810

>, 48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

3810

>, 7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 37.5 kg ha⁻¹

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)

> 200

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.79

Rat

Other Mammal toxicity endpoints

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

0.002

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

0.05

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

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

0.03

Dog SF=100

Dermal penetration studies (%)

6.5-10.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

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

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Code is usually 9 or 6.1

CLP classification 2013

Health: H302, H317, H319, H331, H361, H371
Environment: H400, H410

EC Risk Classification

T - Toxic: R23, Xn - Harmful: R22, R43
Xi - Irritant: R36
N - Dangerous for the environment: R50, R53

EC Safety Classification

S20/21, S2, S13, S46, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 2811

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

quinoclamine

French

quinoclamine

German

Quinoclamin

Danish

quinoclamin

Italian

quinoclamine

Spanish

quinoclamina

Greek

Polish

kwinoklamina

Swedish

kvinoklamin

Hungarian

Dutch

quinoclamine

Record last updated:	08/03/2021
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