Cyclanilide (Ref: RPA 090946)

Cyclanilide (Ref: RPA 090946)	Last updated: 21/08/2024
(Also known as: cyclanilid)

SUMMARY

Cyclanilide is a plant growth regulator. It has a low aqueous solubility and is relatively volatile. It is not persistent in soil systems but may be in water under some conditions. Cyclanilide has a low mammalian toxicity but may cause adverse reproduction/development effects and is a possible neurotoxin. It is moderately toxic to most fauna and flora.

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: GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health High alert: Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

A plant growth regulator used in a variety of situations including acting as a harvest aid for cotton

Example pests controlled

Apical dominance; Plant shape

Example applications

Cotton; Ornamentals including ficus, hydrangea, carmellia, convolvulus, gardenia, holly, spirea, tree lilac; Fruit including cherry, apple, pear, plum

Efficacy & activity

Availability status

Current

Introduction & key dates

1995, registered Argentina

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

Austria/Greece

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

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

Australia, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₁H₉Cl₂NO₃

Canonical SMILES

C1CC1(C(=O)NC2=C(C=C(C=C2)Cl)Cl)C(=O)O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

GLWWLNJJJCTFMZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H9Cl2NO3/c12-5-1-2-9(8(13)3-5)14-10(15)6-4-7(6)11(16)17/h1-3,6-7H,4H2,(H,14,15)(H,16,17

2D structure diagram/image available?

Yes

General status

Pesticide type

Plant Growth Regulator

Substance groups

Anilide PGR; Monocarboxylic acid compound

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - 2,4-dichloroaniline <1 g kg⁻¹

Substance origin

Synthetic

Mode of action

Inhibits the transport of auxin particularly in meristematic plant tissue

CAS RN

113136-77-9

EC number

419-150-7

CIPAC number

586

US EPA chemical code

026201

PubChem CID

11097730

CLP index number

616-110-00-2

Molecular mass

274.10

PIN (Preferred Identification Name)

1-[(2,4-dichlorophenyl)carbamoyl]cyclopropane-1-carboxylic acid

IUPAC name

1-(2,4-dichloroanilinocarbonyl)cyclopropanecarboxylic acid

CAS name

1-[[(2,4-dichlorophenyl)amino]carbonyl]cyclopropanecarboxylic acid

Other status information

Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

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

Aventis CropScience
Bayer CropScience

Example products using this active

Tiberon SC

Formulation and application details

Usually supplied as a suspension concentrate for broadcast spraying

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

Hexane

600

Toluene

59100

Methanol

52900

Acetone

Melting point (°C)

195

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.78 X 10⁰³

Calculated

Log P

3.25

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.48

Dissociation constant pKa) at 25 °C

3.5

Weak acid

Vapour pressure at 20 °C (mPa)

0.0084

Low volatility

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

7.41 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

211nm = 29840, 256nm = 21249, 290nm = 1215

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)

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 15-49 days, DT₉₀ range 65.6-78.5 days, field study DT₅₀ range 11-45 days (France 7 Spain), DT₉₀ range 37-151 days; Other sources: 75 days (DW4)

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

Stable

Note

pH variable: DT₅₀ 50 days at pH 5, 54 days at pH 9, summer USA

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

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Slow

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)

358

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Adsorption decreases as pH increases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.09

Calculated

Transition state

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

Value

8.05 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

0.4

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

2,4-dichloroaniline

Major fraction

0.160

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)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Dog 1 yr

(ppm diet)

160

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 216

Unknown species

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1240 mg kg feed⁻¹

Unknown species

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

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

> 469

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

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

Dose: Field rate

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)

> 100

Apis mellifera

Low

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

89.5

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)

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)

Oncorhynchus mykiss

Moderate

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

2.6

Pimephales promelas

Moderate

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

4.48

Danio rerio EC₅₀ Embryo

Moderate

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

Daphnia magna

Moderate

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

12.6

Daphnia magna

Low

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

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

4.0

Americamysis bahia

Moderate

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)

0.22

Lemna gibba

Moderate

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

1.7

Raphidocelis 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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

5.15

Rat (nose only)

Other Mammal toxicity endpoints

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

0.0075

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

0.015

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

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

0.0045

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

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

; ; ; ;

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

Moderately toxic

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 6.1
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302
Environment: H411

WHO Classification

Not listed (Not listed)

UN Number

UN2811

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Material is stable under ambientl conditions

TRANSLATIONS

Language

Name

English

cyclanilide

French

cyclanilide

German

Cyclanilid

Danish

cyclanilid

Italian

ciclanilide

Spanish

ciclanilida

Greek

cyclanilide

Polish

cyklanilid

Swedish

Hungarian

Dutch

cyclanilide

Norwegian

Record last updated:	21/08/2024
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