Flubendiamide (Ref: NNI-0001)

Flubendiamide (Ref: NNI-0001)	Last updated: 27/06/2024
(Not known by any other names)

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 High alert: Very persistent; GUS: High leachability	Ecotoxicity High alert: Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description

A broad spectrum insecticide for use in wide range of annual and perennial crops.

Example pests controlled

Various Lepidopterous spp. including armyworms, corn borers, cutworms, diamondback moths, loopers

Example applications

Corn; Cotton; Tobacco; Fruit including apples pears, stone fruit; Nuts; Grapes; Various vegetables

Efficacy & activity

Availability status

Current

Introduction & key dates

1979, first reported

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/11/2024

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Greece

Date EC 1107/2009 inclusion expires

31/08/2024

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, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₂₃H₂₂F₇IN₂O₄S

Canonical SMILES

CC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)F)NC(=O)C2=C(C(=CC=C2)I)C(=O)NC(C)(C)CS(=O)(=O)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

ZGNITFSDLCMLGI-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C23H22F7IN2O4S/c1-12-10-13(21(24,22(25,26)27)23(28,29)30)8-9-16(12)32-18(34)14-6-5-7-15(31)17(14)19(35)33-20(2,3)11-38(4,36)37/h5-10H,11H2,1-4H3,(H,32,34)(H,33,35)/f/h32-33H

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Phthalamide insecticide; Organofluoride insecticide

Minimum active substance purity

960

Known relevant impurities

Substance origin

Synthetic

Mode of action

Exhibits larvicidal activity as an orally ingested toxicant by targeting and disrupting the Ca2+ balance. Ryanodine receptor modulator.

CAS RN

272451-65-7

EC number

608-064-7

CIPAC number

788

US EPA chemical code

027602

PubChem CID

11193251

CLP index number

No data found

Molecular mass

682.39

PIN (Preferred Identification Name)

N1-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-3-iodo-N2-[1-(methanesulfonyl)-2-methylpropan-2-yl]benzene-1,2-dicarboxamide

IUPAC name

3-iodo-N'-(2-mesyl-1,1-dimethylethyl)-N-{4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-o-tolyl}phthalamide

CAS name

N2-(1,1-dimethyl-2-(methylsulfonyl)ethyl)-3-iodo-N1-(2-methyl-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)phenyl)-1,2-benzenedicarboxamide

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

Colourless, odourless crystalline solid

Formulations

Property

Value

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

Bayer CropScience
Nippon soda

Example products using this active

Belt
Fame
Fenos
Synapse
Pheonix

Formulation and application details

Usually supplied as a suspension concentrate or wettable granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.029

Low

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

488

p-Xylene

0.835

n-heptane

26000

methanol

8120

1,2-dichloroethane

Melting point (°C)

217.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

255

Flashpoint (°C)

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

1.38 X 10⁰⁴

Calculated

Log P

4.14

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.66

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.1

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral soln: 204.4nm=39066
Acidic soln: 203nm=40500
Basic soln: 218nm=24967

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

500

Very persistent

DT₅₀ (lab at 20 °C)

500

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ >365days

Dissipation rate RL₅₀ (days) on plant matrix

Value

2.9

Note

Published literature RL₅₀ range 0.7-6.1 days, 4 crops field & undercover, various matrices, n=7

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.75

Note

Published literature RL₅₀ range 0.58-5.0 days, 5 field grown crops field, various matrices, n=9

Aqueous photolysis DT₅₀ (days) at pH 7

Value

32.5

Stable

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

500

Stable

Water phase only DT₅₀ (days)

6.9

Moderately fast

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)

Slightly mobile

K_oc (mL g⁻¹)

2197

Notes and range

Literature values range 1076-3318 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

22.7

Moderately mobile

K_foc (mL g⁻¹)

334

¹/_n

0.095

Notes and range

EU dossier K_f range 17.2-30.0 mL g⁻¹, K_foc range 1076-3318 mL g⁻¹, ¹/_n range 0.965-1.022, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.98

Calculated

High leachability

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

Value

1.33 X 10⁰⁰

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

8.8

Calculated using the Atkinson method. Assumed 0.5E+06 OH/cm³, 24 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

4.7

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

N-(4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl)-3-hydroxy-N-(2-methyl-1-(methylsulfonyl)propan-2-yl)phthalamide

Minor fraction

0.071

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

5-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-[(3-iodo-2-{[2-methyl-1-(methylsulfonyl)propan-2-yl]carbamoyl}benzoyl)amino]benzoic acid (Ref: NNI-0001-benzoic acid)

A-18

2-[2-methyl-1-(methylsulfonyl)propan-2-yl]-1Hisoindole-1,3(2H)-dione (Ref: NNI-0001-des-iodoalkylphthalimide)

A-27

{[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]amino}(oxo)acetic acid (Ref: NNI-0001-oxalinic acid)

A-31

N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-3-hydroxy-N-[2-methyl-1-(methylsulfonyl)propan-2-yl]phthalamide (Ref: NNI-0001-3-OH)

A-2

N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl]-3-hydroxy-N-[2-methyl-1-(methylsulfonyl)propan-2-yl]phthalamide (Ref: NNI-0001-3-OH-hydroxyperfluoroalkyl)

A-10

2-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-4-iodo-1Hisoindole-1,3(2H)-dione (Ref: NNI-0001-iodophthalimide)

A-14

N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(hydroxymethyl)phenyl]-3-iodo-N-[2-methyl-1-(methylsulfonyl)propan2-yl]phthalamide (Ref: NNI-0001-benzylalcohol)

A-16

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

>= 2000

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

200

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: 2.24 kg ha⁻¹

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)

> 200

Apis mellifera

Low

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

> 200

Apis mellifera

Low

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

Chronic

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

407

Coccinella septempunctata

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

> 180

Chrysoperla carnea

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

> 675

Aphidius rhopalosiphi

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

> 675

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)

0.06

Oncorhynchus mykiss

High

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

0.060

Pimephales promelas

Moderate

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

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

0.06

Daphnia magna

High

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

0.033

Daphnia magna

Moderate

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

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

> 0.028

Americamysis bahia

High

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

1.188

Chironomus riparius

Moderate

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

0.035

Chironomus riparius

Moderate

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

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

0.0546

Lemna gibba

Moderate

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

0.069

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

0.053

Outdoor pond life

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

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

>= 0.069

Rat

Other Mammal toxicity endpoints

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

0.017

Rat SF=100

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

0.1

Rat SF=100

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

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

0.006

Dog SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No anticipated risks

Occupational

No anticipated risks

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

EU MRL levels for some commodities subject to change in mid-2022

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Mainly via faeces and bile.

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, thyroid & kidney 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

Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flubendiamide

French

German

Danish

Italian

Spanish

Greek

Polish

flubendiamid

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	27/06/2024
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