Chlorantraniliprole (Ref: DPX E2Y45)

Chlorantraniliprole (Ref: DPX E2Y45)	Last updated: 10/12/2019
(Also known as: rynaxypyr; IN-E2Y45)

GENERAL INFORMATION

Description

Used to control a broad spectrum of pests on a range of crops including potatoes and cotton.

Example pests controlled

Cabbage loopers; Corn borers; Armyworms; Cutworms

Example applications

Potatoes; Grapes; Cotton

Efficacy & activity

Availability status

Current

Introduction & key dates

2007

UK regulatory status

UK approval status

Approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Approved

Dossier rapporteur/co-rapporteur

Ireland

Date inclusion expires

30/04/2024

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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

Canada; USA; Australia; Korea; New Zealand; Argentina; China; Chile; Colombia; Honduras; Indonesia; Vietnam

Chemical structure

Isomerism

Chemical formula

C₁₈H₁₄BrCl₂N₅O₂

Canonical SMILES

CC1=C(C(=CC(=C1)Cl)C(=O)NC)NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

PSOVNZZNOMJUBI-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H14BrCl2N5O2/c1-9-6-10(17(27)22-2)15(12(21)7-9)24-18(28)13-8-14(19)25-26(13)16-11(20)4-3-5-23-16/h3-8H,1-2H3,(H,22,27)(H,24,28)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Anthranilic diamide

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier: acetonitrile <3 g kg⁻¹; 3-picoline <3 g kg⁻¹; methanesulfonic acid <2 g kg⁻¹

Substance origin

Synthetic

Mode of action

Exhibits larvicidal activity as an orally ingested toxicant by targeting and disrupting the Ca2+ balance; Ryanodine receptor (Group 28)

CAS RN

500008-45-7

EC number

CIPAC number

794

US EPA chemical code

090100

PubChem CID

11271640

Molecular mass

483.15

PIN (Preferred Identification Name)

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

IUPAC name

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

CAS name

3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

Other status information

PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Fine crystalline off-white powder

Formulations

Property

Value

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

Acelepryn
Coragen
DuPont E2Y45 SC
Altacot
Ferterra
Prevathon

Example products using this active

DuPont
Syngenta
Scotts Company

UK LERAP status

No UK approval for use as a pesticide under EC Regulation 1107/2009

Formulation and application details

Usually supplied as a suspension concentrate or as water dispersible granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.88

Low

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

3446

Acetone

1714

Methanol

1144

Ethyl acetate

162

o-Xylene

Melting point (°C)

209

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

330

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

7.24 X 10⁰²

Calculated

Log P

2.86

Moderate

Bulk density (g ml⁻¹)

1.51

Dissociation constant pKa) at 25 °C

10.88

Very weak acid

Vapour pressure at 20 °C (mPa)

6.3 X 10^-09

Low volatility

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

3.2 X 10^-09

Non-volatile

GUS leaching potential index

3.51

Calculated

High leachability

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

Value

6.81 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

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

Acidic solution: no absorption max >200nm, 290nm = 3941
Neutral solution: no absorption max >200nm, 290nm = 4185
Basic solution: absorption max at ~320nm, 290nm = 6082

Surface tension (mN m⁻¹)

72.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

597

Very persistent

DT₅₀ (lab at 20 °C)

597

Very persistent

DT₅₀ (field)

204

Persistent

DT₉₀ (lab at 20 °C)

1183

Very persistent

DT₉₀ (field)

1677

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 270-1163 days, DT₉₀ range 742-2205 days, Field studies DT₅₀ range 123-561 days, DT₉₀ range 404-5628 days; Manufacturers published data gives DT₅₀ between 3-12 months, shorter in the presence of crop cover

Dissipation rate RL₅₀ on plant matrix

Value

1.3

Note

Cauliflower curd, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

4.5

Note

Published literature RL₅₀ range 2.2-9.9 days, 4 field grown crops, fruit & straw, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.31

Fast

Note

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

Value

Stable

at 25 °C

Stable

Note

pH 4: stable at 25 °C; pH 9: unstable at 25 °C

Water-sediment DT₅₀ (days)

170

Slow

Water phase only DT₅₀ (days)

23.5

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

3.18

Moderately mobile

K_oc

362

Notes and range

EU dossier K_d range 0.803-8.88 mL g⁻¹, K_oc range 244-464 mL g⁻¹, soils-5

Freundlich

K_f

2.95

Moderately mobile

K_foc

301

¹/_n

0.95

Notes and range

EU dossier K_f range 0.633-9.16 mL g⁻¹, K_foc range 180-539 mL g⁻¹, ¹/_n range 0.849-1.003, Soils = 5

pH sensitivity

None

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2,6-dichloro-4-methyl-11H-pyrido(2,1-beta)quinazolin-11-one (Ref: IN-ECD73)

Soil

0.049

Minor fraction, Relevant

5-bromo-N-methyl-1H-pyrazole-3-carboxamide (Ref: IN-F6L99)

Soil

0.021

Minor fraction, Relevant

2-(3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl)-6-chloro-8-methyl-4(3H)-quinazoline (Ref: IN-GAZ70)

Soil

0.044

Minor fraction, Relevant

2-(3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl)-6-chloro-3, 8dimethyl-4(3H)-quinazolinone (Ref: IN-EQW78)

Soil

0.095

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (Ref: IN-DBC80)

3-bromo-1H-pyrazole-3-carboxylic acid (Ref: IN-EVK64)

N-(2-(aminocarbonyl_4-4chloro-6-methylphenyl)-3-bromo-1-(3-chloro-2-pyridinyl)IH-pyrazole-5-carboxamide (Ref: IN-F9N04)

Soil; Sediment; Water

2-(((3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-yl)carbonyl)amino)-5-chloro-3-methylbenzoic acid (Ref: IN-GKQ52)

3-bromo-N-(4-chloro020((hydroxymethyl)amino)carbonyl)-6-methylphenyl)-1-)3-chloro-2-pyridinyl)-1H-pyrazole-5-carboximide (Ref: IN-H2H20)

Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

1.5

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1729 mg kg⁻¹ BW/day

Colinus virginianus

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 12.0

Cyprinodon variegatus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.11

Oncorhynchus mykiss

Moderate

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

0.0116

Daphnia magna

High

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

0.00447

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)

0.0025

Chironomus riparius

High

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

0.05

Chironomus riparius

High

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

> 2.0

Lemna gibba

Moderate

Non-target plants

> 300

Ryegrass
Vegetative vigour, ER₅₀
as g ha⁻¹

> 300

Ryegrass
Seedling emergence, ER₅₀
as g ha⁻¹

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

> 4.0

Pseudokirchneriella subcapitata

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)

> 100

Apis mellifera

Low

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

> 104.1

Apis mellifera

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)

> 100

Bombus terrestris

Low

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

> 100

Bombus terrestris

Low

Mason bees (Osmia spp.)

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

5.92

Osmia bicornis

Moderate

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)

> 1000

Eisenia foetida

Low

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

350

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

100

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

750

>
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

750

>
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 0.7 mg/kf soil 28 days

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.1

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

1.56

Mouse SF=100

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)

0.2

Mouse SF=100

Dermal penetration studies (%)

1.9-4.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk considering proposed uses

Occupational

Low risk considering proposed uses

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive
Not senstive to thermal, friction on impact shock

CLP classification 2013

Health: H319, H335
Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

chlorantraniliprole

French

German

Danish

Italian

Spanish

clorantranilipol

Greek

Polish

chlorantraniliprol

Swedish

Hungarian

Dutch

Record last updated:	10/12/2019
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