Cyantraniliprole (Ref: DPX-HGW86)

Cyantraniliprole (Ref: DPX-HGW86)	Last updated: 31/10/2024
(Not known by any other names)

SUMMARY

An insecticide for the control of chewing and sucking pests. It has a low aqueous solubility and is non-volatile. It is not expected to be persistent in soil or water systems. It has a low mammalian toxicity and a low potential to bioaccumulate. No significant health issues have been identified. It is highly toxic to honeybees, moderately toxic to earthworms and 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: Moderately persistent; GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity High alert: Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health Low alert

GENERAL INFORMATION

Description

A broad sprectrum insecticide for a wide range of crops that is effective against many key chewing and sucking pests

Example pests controlled

Whitefly; Thrips; Aphids; Fruitflies; Psyllids; Fruit worms

Example applications

Onions; Potatoes; Field tomatoes; Vegetables incuding brassica, cucurbit, fruiting, and leafy vegetables, as well as greenhouse-grown aubergine, pepper, and tomato

Efficacy & activity

Availability status

Current

Introduction & key dates

2008, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

14/09/2031

GB LERAP status

Check label - may vary with formulationl

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

United Kingdom/France

Date EC 1107/2009 inclusion expires

14/09/2026

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

China, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₉H₁₄BrClN₆O₂

Canonical SMILES

CC1=CC(=CC(=C1NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br)C(=O)NC)C#N

Isomeric SMILES

International Chemical Identifier key (InChIKey)

DVBUIBGJRQBEDP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H14BrClN6O2/c1-10-6-11(9-22)7-12(18(28)23-2)16(10)25-19(29)14-8-15(20)26-27(14)17-13(21)4-3-5-24-17/h3-8H,1-2H3,(H,23,28)(H,25,29)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Diamide insecticide; Pyridylpyrazole insecticide

Minimum active substance purity

940 g/Kg

Known relevant impurities

EU dossier: methansulfonic acid <2 g kg⁻¹; heptane <7g kg⁻¹, 3-picoline <3g kg⁻¹; IN-Q6S09 <1mg kg⁻¹; IN-RYA13 <20mg kg⁻¹

Substance origin

Synthetic

Mode of action

Exhibits larvicidal activity as an orally ingested toxicant by targeting and disrupting the Ca2+ balance, Second generation ryanodine receptor, Foliar and systemic activity

CAS RN

736994-63-1

EC number

680-242-7

CIPAC number

998

US EPA chemical code

090098

PubChem CID

11578610

CLP index number

No data found

Molecular mass

473.72

PIN (Preferred Identification Name)

3-bromo-1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-1H-pyrazole-5-carboxamide

IUPAC name

3-bromo-1-(3-chloro-2-pyridyl)-4'-cyano-2'-methyl-6'-(methylcarbamoyl)pyrazole-5-carboxanilide

CAS name

3-bromo-1-(3-chloro-2-pyridinyl)-N-(4-cyano-2-methyl-6-((methylamino)carbonyl)phenyl)-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

None identified

Physical state

White powdery solid

Formulations

Property

Value

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

DuPont
Syngenta
Nippon soda

Example products using this active

Cyazypyr
Benevia
Exirel
Verimark
Mainspring

Formulation and application details

Applied directly to soil but may also be used as a seed treatment or foliar spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

14.2

Low

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

6540

Acetone

1960

Ethyl acetate

576

Toluene

4730

Methanol

Melting point (°C)

224

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

350

Flashpoint (°C)

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

1.05 X 10⁰²

Calculated

Log P

2.02

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

8.8

Vapour pressure at 20 °C (mPa)

5.13 X 10^-12

Low volatility

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

1.7 X 10^-13

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)

69.4

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

34.4

Moderately persistent

DT₅₀ (lab at 20 °C)

34.4

Moderately persistent

DT₅₀ (field)

32.4

Moderately persistent

DT₉₀ (lab at 20 °C)

226.4

Persistent

DT₉₀ (field)

177.4

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 8.7-91.9 days, DT₉₀ range 66.2-376 days; Field studies DT₅₀ range 16.9-51.3 days, DT₉₀ range 55.5-257.4 days; Literature data lab studies DT₅₀ range 3.4-21.6 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

35.0

Cabbage Leaves

Note

Laboratory study

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

3.7

Note

Published data RL₅₀ range 2.2-5.2 days for 6 field grown crops, various matrices, n=7

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.22

Fast

Note

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

Value

Moderately persistent

Note

pH sensitive 261 days at pH4; 1.8 days at pH9 all at 20 °C

Water-sediment DT₅₀ (days)

7.03

Fast

Water phase only DT₅₀ (days)

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)

3.73

Moderately mobile

K_oc (mL g⁻¹)

241

Notes and range

EU dossier K_d range 2.51-7.14 mL g⁻¹, koc range 157 to 367 mL g⁻¹. Soils=5

Freundlich

K_f (mL g⁻¹)

2.95

Moderately mobile

K_foc (mL g⁻¹)

193

¹/_n

0.93

Notes and range

EU dossier K_f range 2.05-5.05 mL g⁻¹, K_foc range 155-266 mL g⁻¹, ¹/_n range 0.895-0.958, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.59

Calculated

Transition state

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

Value

1.60 X 10^-01

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

8.0

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)

1.0

Whole fish

Low potential

CT₅₀ (days)

No data

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-(((3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)carbonyl)amino)-N3,5-dimethylisophthalamide (Ref: IN JCZ38)

Major fraction

0.396

4-(((3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)carbonyl)amino)-3-methyl-5-(methylcarbamoyl)benzoic acid (Ref: IN JSE76)

Major fraction

0.429

2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3,8-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxamide (Ref: IN K5A77)

Major fraction

0.288

6-chloro-4-methyl-11-oxo-11H-pyrido[2,1-b]quinazoline-2-carbonitrile (Ref: IN-N5M09)

Minor fraction

2-(2-bromo-4-oxopyrazolo[1,5-a]pyrido[3,2-e]pyrazin-5(4H)-yl)-5-cyano-N,3-dimethylbenzamide (Ref: IN-RNU71)

Minor fraction

4-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-methylisophthalamide (Ref: IN-K7H19)

Minor fraction

2-(5-bromo-1H-pyrazol-3-yl)-3,8-dimethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-6-carbonitrile (Ref: IN-QKV54)

Minor fraction

Photolysis

2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3,8-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carbonitrile (Ref: IN J9Z38)

Major fraction

0.719

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)

amitriptyline

Relevancy unknown

3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (Ref: IN-M2G98)

Not relevant

4-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-3-carbamoyl-5-methylbenzoic acid (Ref: IN-K5A79)

Not relevant

4-(((3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)carbonyl)amino)-3-methyl-5-(methylcarbamoyl)benzoic acid (Ref: IN JSE76)

Not relevant

2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]-8-methyl-4-oxo-1,4-dihydroquinazoline-6-carboxylic acid (Ref: IN-PLT97)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-bromo-N-methyl-1H-pyrazole-5-carboxamide

IN-F6L99

Plant; Surface water (hydrolysis)

2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]-3,8-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carbonitrile

IN-J9Z38

Rat

6-chloro-4-methyl-11-oxo-11H-pyrido[2,1-b]quinazoline-2-carbonitrile

IN-N5M09

Plant

3-bromo-1-(3-chloropyridin-2-yl)-N-[4-cyano-2-(hydroxymethyl)-6-(methylcarbamoyl)phenyl]-1H-pyrazole-5-carboxamide

IN-N7B69

Plant; Storage

2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]-8-methyl-4-oxo-1,4-dihydroquinazoline-6-carbonitrile

IN-MLA84

Plant; Storage

4-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-methylisophthalamide

IN-K7H19

Storage

3-bromo-1-(3-chloropyridin-2-yl)-N-{4-cyano-2-[(hydroxymethyl)carbamoyl]-6-methylphenyl}-1H-pyrazole-5-carboxamide

IN-MYX98

Storage; Milk

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)

(ppm diet)

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

≥ 1167

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

93.2

Colinus virginianus

Moderate

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

> 945

Eisenia foetida

Moderate

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)

> 0.0934

Apis mellifera

High

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

> 0.1055

Apis mellifera

High

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

Chronic

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 3 hrs - USEPA data]

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)

> 0.54

Bombus impatiens

High

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

61.5

Coccinella septempunctata

Beneficial insects (Lacewings) as Mortality LR₅₀ g ha⁻¹

260.9

Chrysoperla Carnea

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

0.102

Aphidius rhopalosiphi

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

> 230

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)

> 12.6

Oncorhynchus mykiss

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)

> 0.020

Daphnia magna

High

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)

1.2

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

719

Chironomus riparius 48 hr LC₅₀

Low

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)

> 12.1

Lemna gibba

Low

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

> 13.0

Pseudokirchneriella subcapitata

Low

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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.2

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)

Not 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)

0.007

Dog SF=100+

Dermal penetration studies (%)

0.1-0.6

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No significant risks identified for pattern of use proposed

Occupational

No significant risks identified for pattern of use proposed

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Adjustment made to GB MRL for Cyantraniliprole/blackberries, raspberries, Chinese cabbages (pe-tsai) and leeks from June 2022

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

Potential skin senistiser
Some risk of thyroid effects
Possible liver toxicant

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 9
Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H315, H319, H335
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

cyantraniliprole

French

cyantraniliprole

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

cyantraniliprol

Record last updated:	31/10/2024
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