Indoxacarb (Ref: DPX KN128)

Indoxacarb (Ref: DPX KN128)	Last updated: 31/10/2024
(Also known as: DPX KN127; DPX MP062; S-indoxacarb)

SUMMARY

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: Potential for particle bound transport: Medium	Ecotoxicity High alert: Birds acute ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Neurotoxicant

GENERAL INFORMATION

Description

An insecticide for use on a wide range of crops to control certain Lepidoptera, cockroaches and ants

Example pests controlled

Beet armyworm, Fire ants; Cockroaches; Caterpillars

Example applications

Cotton; Brassicas; Sweet corn; Lettuce; Fruiting vegetables; Fruit including apples, pears, cherries

Efficacy & activity

Availability status

Current

Introduction & key dates

1996, first reported; 2000, first registered & marketed USA

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France/Spain

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, Cameroon, India, New Zealand, Africa, Senegal, Morocco

Chemical structure

Isomerism

A chiral molecule, existing in the R- and S-forms but normally used as the S-stereosomer

Chemical formula

C₂₂H₁₇ClF₃N₃O₇

Canonical SMILES

COC(=O)C12CC3=C(C1=NN(CO2)C(=O)N(C4=CC=C(C=C4)OC(F)(F)F)C(=O)OC)C=CC(=C3)Cl

Isomeric SMILES

COC(=O)[C@]12CC3=C(C1=NN(CO2)C(=O)N(C4=CC=C(C=C4)OC(F)(F)F)C(=O)OC)C=CC(=C3)Cl

International Chemical Identifier key (InChIKey)

VBCVPMMZEGZULK-NRFANRHFSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3/t21-/m0/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
indoxacarb	-

General status

Pesticide type

Insecticide

Substance groups

Oxadiazine insecticide

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU 2017 dossier - 4,4'-methylenebis(N,N-diethylaniline < 0.0025 g kg⁻¹

Substance origin

Synthetic

Mode of action

Contact and stomach action. Voltage-dependent sodium channel modulator.

CAS RN

173584-44-6

EC number

605-683-4

CIPAC number

612

US EPA chemical code

118200

PubChem CID

107720

CLP index number

607-700-00-0

Molecular mass

527.83

PIN (Preferred Identification Name)

methyl (S)-N-[7-chloro-2,3,4a,5-tetrahydro-4a-(methoxycarbonyl)indeno[1,2-e][1,3,4]oxadiazin-2-ylcarbonyl]-4'-(trifluoromethoxy)carbanilate

IUPAC name

methyl (S)-N-[7-chloro-2,3,4a,5-tetrahydro-4a-(methoxycarbonyl)indeno[1,2-e][1,3,4]oxadiazin-2-ylcarbonyl]-4'-(trifluoromethoxy)carbanilate

CAS name

methyl (4aS)-7-chloro-2,5-dihydro-2-(((methoxycarbonyl)(4-(trifluoromethoxy)phenyl)amino])carbonyl)indeno(1,2-e)(1,3,4)oxadiazine-4a(3H)-carboxylate

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)

22A

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Earias vittella, Heliothis virescens, Musca domestica, Choristoneura rosaceana, Plutella xylostella, Spodoptera litura

Physical state

White powder

Formulations

Property

Value

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

DuPont
BOC Sciences
Agro-Alliance (Australia) Pty Ltd

Example products using this active

Provaunt
Steward
Avaunt
Cockroach H-Kill Bait Station

Formulation and application details

Often supplied as wettable granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.2

Low

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

160000

Ethyl acetate

250000

Acetone

1720

Heptane

117000

Xylene

Melting point (°C)

88.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

235

Flashpoint (°C)

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

4.47 X 10⁰⁴

Calculated

Log P

4.65

at 25 °C

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies. Higher total residues in fat compared to fat free muscle.

Density (g ml⁻¹)

1.44

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

9.8 X 10^-06

Low volatility

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

6.00 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

From soil surface

Negligible

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

pH 0.91: 203nm=18075, 230nm=14342, 285nm=17871, 311nm=21106
pH 7.05: 235nm=9272, 285nm=16345, 290nm=15290, 311nm=20502
pH 12.67: 235nm=17682, 285nm=16437, 290nm=15653, 311nm=20098

Surface tension (mN m⁻¹)

76.8

at 20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

113.2

Persistent

DT₅₀ (lab at 20 °C)

113.2

Persistent

DT₅₀ (field)

5.97

Non-persistent

DT₉₀ (lab at 20 °C)

119

Persistent

DT₉₀ (field)

25.7

DT₅₀ modelling endpoint

Note

EU 2018 dossier lab studies DT₅₀ range 65.3-231 days, DT₉₀ range 15.7-404 days, Soils=5, Field studies DT₅₀ range 4.9-7.5 days, DT₉₀ range 23.5-31.2 days, Soils=4; EU 2005 dossier Lab studies DT₅₀ range 2-11 days, Feld study DT₅₀ range 10-27 days. Other sources: DT₅₀ 4.5-117 days aerobic, 12.8-402 days anaerobic

Dissipation rate RL₅₀ (days) on plant matrix

Value

3.4

Note

Eggplant fruit, n=1; RL₅₀=18 days on cabbage leaves, lab study.

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

6.33

Note

Published literature RL₅₀ range 0.815.8 days, 3 field and undercover crops, various matrices, n=3; Persimmon peeled fruit RL₅₀=20 days

Aqueous photolysis DT₅₀ (days) at pH 7

Value

4.5

Moderately fast

Note

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

Value

17.6

Non-persistent

Note

pH sensitive: stable at pH 4, 0.4 days at pH 9 at 20 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

1.4

Moderately fast

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

[Wheat grain: 120 days @ 25 DegC, 65% RH, Lab study], [Maize: 120 days @ 25 DegC, 65% RH; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

46.3

Non-mobile

K_oc (mL g⁻¹)

4483

Notes and range

EU 2018 dossier K_d range 26-95 mL g⁻¹, K_oc range 2500-9600 mL g⁻¹, Soils=4; Literature values range 2200-8200 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.27

Calculated

Low leachability

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

Value

5.07 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

77.3

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

methyl [4-(trifluoromethoxy)phenyl]carbamate (Ref: IN-KB687)

Minor fraction

methyl 5-chloro-2,3-dihydro-2-hydroxy-1-[[[[4-trifluoromethoxy)phenyl]amino]carbonyl]hydrazono]-1H-indene-2-carboxylate (Ref: IN-JU873)

Major fraction

0.129

7-chloro-2,4-dihydro-4-[4(trifluoromethoxy)phenyl]3H-indeno[2,1-e]-1,2,4-triazin-3-one (Ref: IN-ML438)

Minor fraction

0.097

Soil DT50 = 43.4 days; Koc = 692 mL/g

methyl-7-chloro-2,5-dihydro-2-(((trifluoromethoxy)phenyl)amino)carbonyl(indeno(1,3,4)oxadiazine-4a(3H)-carboxylate (Ref: IN JT333)

Major fraction

0.186

(E)-methyl 5-chloro-2,3-dihydro-2-hydroxy-1-((((methoxycarbonyl)(4-trifluoromethoxy)phenyl)amino)carbonyl)hydrazono)-1H-indene-2-carboxylate (Ref: IN KG433)

Major fraction

0.400

(4-trifluoromethoxy)phenyl urea (Ref: IN MK638)

Major fraction

0.280

sodium 7-cholor-2,5,-dihydro-2-[[methoxycarbonyl)[4(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid (Ref: IN-KT413)

Major fraction

0.184

1,3-dihydro-5-(trifluoromethoxy)-2H-benzimidazol-2-one (Ref: IN-MK643)

Major fraction

0.120

Soil DT50 = 235.2 days; Koc = 692 mL/g

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

methyl 2-[[[4(trifluoromethoxy)phenyl]amino]carbonyl]hydrazine carboxylate (Ref: IN-MF014)

Water (a = Hydrolysis, b = Photolysis)

a=0.150; b=0.376

2-(carboxymethyl)-4-chlorobenzoic acid (Ref: IN-MA573)

Water (Photolysis)

0.199

sodium 7-cholor-2,5,-dihydro-2-[[methoxycarbonyl)[4(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid (Ref: IN-KT413)
Note: Soil DT50 = 2.6 days; Koc = 422 mL/g

Water (Hydrolysis)

methyl 6-chloro-3,4-dihydro-1-oxo-1H-2-benzopyran-3-carboxylate (Ref: IN-MH304)

Water (Photolysis)

0.323

methyl (4aS)-7-chloro-2-{[4-(trifluoromethoxy) phenyl]carbamoyl}-2,5-dihydroindeno[1,2-e] [1,3,4]oxadiazine-4a(3H)-carboxylate (Ref: IN-KN-125)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

179

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

73.5

Colinus virginianus

High

Birds - Short term dietary (LC₅₀/LD₅₀)

340 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

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

> 625

Eisenia foetida as isomer mix corr

Moderate

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

>= 29.2

Eisenia foetida 56 day

Moderate

Soil micro-organisms

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

Dose: 0.25 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

125

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

0.08

Apis mellifera

High

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

0.232

Apis mellifera

High

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

0.0649

Apis mellifera

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 24 hrs - USEPA data]

Bumblebees (Bombus spp.)

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

0.25

Bombus terrestris

High

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

> 0.07

Bombus terrestris

High

Mason bees (Osmia spp.)

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

1.26

Osmia bicornis

Moderate

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 LC₅₀ ppm

> 5.77

Coccinella septempunctata Adult

Beneficial insects (Lacewings) as Mortality ER₅₀ g ha⁻¹

> 6.9

Chrysoperla carnea

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

> 5.1

Aphidius colemani

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

220.5

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)

> 0.17

Oncorhynchus mykiss

Moderate

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

0.15

Oncorhynchus mykiss 90 day

Moderate

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

> 0.382

Danio rerio

Moderate

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

0.17

Daphnia magna

Moderate

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

3.9

Daphnia magna

Moderate

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

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

0.75

Mysidopsis bahia

Moderate

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

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

0.0018

Chironomus riparius

High

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

0.0029

Chironomus dilutus

High

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

0.084

Lemna gibba

Moderate

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

0.079

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)

179

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.2

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.005

Rat SF=100

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

0.005

Rat SF=100

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

0.003

Rat SF=100

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

0.003

Rat SF=100

Dermal penetration studies (%)

1-18

concentration dependent

Dangerous Substances Directive 76/464

List II

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

Eye irritant

Phototoxicant

General human health issues

Moderately toxic
Possible kidney, liver, spleen and CNS toxicant

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: H301, H317, H332, H372
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2811

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Limited shelf-life

TRANSLATIONS

Language

Name

English

indoxacarb

French

indoxacarbe

German

Indoxacarb

Danish

indoxacarb

Italian

indoxacarb

Spanish

indoxacarb

Greek

Polish

indoksakarb

Swedish

indoxakarb

Hungarian

indoxacarb

Dutch

indoxacarb

Norwegian

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