Cyclaniliprole (Ref: IKI-3106)

Cyclaniliprole (Ref: IKI-3106)	Last updated: 07/06/2024
(Not known by any other names)

SUMMARY

Cyclaniliprole is an insecticide for fruit, greenhouse and some other crops. It has a low aqueous solubility and is non-volatile. It may be environmentally persistent. It has a high to moderate toxicity to most aquatic species, is highly toxic to bees and moderately toxic to earthworms. Cyclanilliprole has a low oral mammalian toxicity.

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 High alert: Persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Daphnia acute ecotoxicity: High; Bees acute oral ecotoxicity: High; Bees acute unknown ecotoxicity: High	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

A diamide insecticide for use mainly on tree fruit, grapes and glasshouse crops

Example pests controlled

Cotton bollworm (Helicoverpa armegera); Leaf miner (Tuta absoluta); Arnyworms; Oriental leafworm moth

Example applications

Tree fruit including apples, pears, plums, peaches and apricots; Cotton; Brassicas; Some glasshouse crops including tomato

Efficacy & activity

Availability status

Current

Introduction & key dates

2013, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

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/France

Date EC 1107/2009 inclusion expires

Not applicable

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

Chemical structure

Isomerism

Cyclaniliprole is a racemic mixture with the R- and S-enantiomers present in a 50:50 w/w ratio.

Chemical formula

C₂₁H₁₇Br₂Cl₂N₅O₂

Canonical SMILES

CC(C1CC1)NC(=O)C2=CC(=CC(=C2NC(=O)C3=CC(=NN3C4=C(C=CC=N4)Cl)Br)Br)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

RAMUASXTSSXCMB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H17Br2Cl2N5O2/c1-10(11-4-5-11)27-20(31)13-7-12(24)8-14(22)18(13)28-21(32)16-9-17(23)29-30(16)19-15(25)3-2-6-26-19/h2-3,6-11H,4-5H2,1H3,(H,27,31)(H,28,32)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Diamide insecticide; Pyridylpyrazole insecticide

Minimum active substance purity

950 g/Kg

Known relevant impurities

EU dossier: None delcared

Substance origin

Synthetic

Mode of action

Ryanodine receptor modulator

CAS RN

1031756-98-5

EC number

694-976-0

CIPAC number

None allocated

US EPA chemical code

PubChem CID

24822142

CLP index number

No data found

Molecular mass

602.1

PIN (Preferred Identification Name)

rac-3-bromo-N-(2-bromo-4-chloro-6-{[(1R)-1-cyclopropylethyl]carbamoyl}phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

IUPAC name

2',3-dibromo-4'-chloro-1-(3-chloro-2-pyridyl)-6'-{((1RS)-1-cyclopropylethyl)carbamoyl}pyrazole-5-carboxanilide

CAS name

3-bromo-N-(2-bromo-4-chloro-6-(((1-cyclopropylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

Other status information

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)

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

Ishihara Sangyo Kaisha

Example products using this active

IKI-3106 50SL

Formulation and application details

Usually supplied as a soluble liquid for application by broadcast air-assisted trailer or for use in hand-held apparatus.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.15

Low

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

170

Xylene

11000

Acetone

4500

Methanol

1400

n-Octanol

Melting point (°C)

241

Boiling point (°C)

Decomposes soon after melting

Degradation point (°C)

246

Flashpoint (°C)

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

5.01 X 10⁰²

Calculated

Log P

2.7

at 40 °C

Moderate

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - no accumulation observed in the cattle feeding study (depuration investigated)

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

8.6

Vapour pressure at 20 °C (mPa)

1.65 X 10^-03

Low volatility

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

6.6 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

pH 6.4: 229.5nm=25020; 271.6nm=14060
pH 1.1: 203.7nm=31760; 229.4nm=20070; 270.9nm=10950
pH 13.2: 246.7nm=20500; 272.3nm=130000; 316.0nm=4149

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1161

Very persistent

DT₅₀ (lab at 20 °C)

1161

Very persistent

DT₅₀ (field)

209

Persistent

DT₉₀ (lab at 20 °C)

3856

Very persistent

DT₉₀ (field)

1176

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 482 - 1728 days, DT₉₀ range 1477 - 5740 days, Soils=9; Field studies DT₅₀ range 167 - 302 days, DT₉₀ range 866 - 1606 days, Soils= 4

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

Note

Water-sediment DT₅₀ (days)

554.4

Stable

Water phase only DT₅₀ (days)

39.94

Stable

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

25.55

Slightly mobile

K_foc (mL g⁻¹)

790

¹/_n

0.99

Notes and range

EU dossier K_f range 2.83-79.2 mL g⁻¹, K_foc range 247-1380 mL g⁻¹, ¹/_n range 0.98-1.00, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.56

Calculated

Transition state

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

Value

1.81 X 10^-01

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

5.04

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-bromo-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-chloropyridin-2-yl)-1H-pyrazole-acid (Ref: NSY-27)

Minor fraction

3-bromo-N-(2-bromo-6-carbamoyl-4-chlorophenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (Ref: YT-1284)

Minor fraction

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

3-bromo-2-((2-bromo-4H-pyrazolo[1,5-d]pyrido[3,2-b][1.4]oxazin-4-ylidene)amino)-5-chloro-N-(1-cyclopropylethyl)benzamide (Ref: NK-1375)

Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-bromo-2-((2-bromo-4H-pyrazolo[1,5-d]pyrido[3,2-b][1.4]oxazin-4-ylidene)amino)-5-chloro-N-(1-cyclopropylethyl)benzamide

NK-1375

Rat; Plant; Surface water

8-bromo-2-(3-bromo-1-(3-hydroxypyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-3-(1-cyclopropylethyl)quinazolin-4(3H)-one

NSY-137

Surface water

2-(2-bromo-4-oxopyrazolo[1,5-a]pyrido[3,2-e]pyrazin-5(4H)-yl)-5-chloro-N-(1-cyclopropylethyl)-3-hydroxybenzamide

NU-536

Surface water

8-bromo-2-(3-bromo-1H-pyrazol-5-yl)-6-chloro-3-(1-cyclopropylethyl)quinazolin-4(3H)-one

TJ-537

Surface water

3-bromo-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-chloropyridin-2-yl)-1H-pyrazole-acid

NSY-27

Rat; Animal

8-bromo-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloroquinazolin-4(3H)-one

NSY-28

Rat

3-bromo-N-(2-bromo-6-carbamoyl-4-chlorophenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

YT-1284

Rat; Plant; Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

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)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

> 500

Eisenia foetida corr

Moderate

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

500

Eisenia foetida corr

Low

Soil micro-organisms

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

Dose: 80 & 400 g ha⁻¹ 28 Day

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)

0.66

Apis mellifera

High

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

0.83

Apis mellifera

High

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) as Mortality LR₅₀ g ha⁻¹

37.5

Coccinella septempunctata Larva

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

0.507

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

105

Typhlodromus pyri

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)

> 0.195

Oncorhynchus mykiss

Moderate

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

0.2

Pimephales promelas 28 day

Moderate

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

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

0.081

Daphnia magna

High

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

0.01

Daphnia magna

Moderate

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)

> 0.0532

Chironomus riparius

High

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

> 0.061

Chironomus riparius

Moderate

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

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

> 0.196

Lemna gibba

Moderate

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

> 0.168

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.62

Rat 4 hr

Other Mammal toxicity endpoints

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

None allocated

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

None allocated

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

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

None allocated

Dermal penetration studies (%)

2-7

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk expected

Occupational

PPC/PPE recommended

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver, thyroid and testis toxicant
Published studies conclude that substance is a suspected carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

cyclaniliprole

French

cyclaniliprole

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	07/06/2024
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