Flubendiamide (Ref: NNI-0001)

Flubendiamide (Ref: NNI-0001)	Last updated: 26/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A new 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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

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
		✓

Also used in

Chemical structure

Isomerism

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

No data

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 group

Benzene-dicarboxamide

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

CAS RN

272451-65-7

EC number

CIPAC number

788

US EPA chemical code

027602

PubChem CID

11193251

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 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

Colourless, odourless crystalline solid

Formulations

Property

Value

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

Belt
Fame
Fenos
Synapse

Example products using this active

Bayer CropScience

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)

Not expected to self ignite; Not highly flammable

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

1.38 X 10⁰⁴

Calculated

Log P

4.14

High

Bulk density (g ml⁻¹)

1.66

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.1

Low volatility

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

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 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 on and in plant matrix

Value

2.9

Note

Published literature RL₅₀ range 1.0-5.0 days, 4 field grown crops field, various matrices, n=8

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

2197

Notes and range

Literature values range 1076-3318 mL g⁻¹

Freundlich

K_f

22.7

Moderately mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.176

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

4.7

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.06

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.060

Pimephales promelas

Moderate

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

0.06

Daphnia magna

High

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

0.033

Daphnia magna

Moderate

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

Non-target plants

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

0.069

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)

> 200

Low

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

> 200

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)

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 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)

> 500

Eisenia foetida corr

Moderate

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

500

Eisenia foetida corr

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

675

Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

675

Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 2.24 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

0.053

Outdoor pond life

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)

>= 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

Notes

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, thyroid & kidney toxicant

Handling issues

Property

Value and interpretation

General

IMDG Transport code
Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

Reproduction risk category 3: R64
N - Dangerous for the environment: R50/53

EC Safety Classification

S2, S13, S36, S57, S46

WHO Classification

III (Slightly hazardous)

UN Number

3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

flubendiamide

French

German

Danish

Italian

Spanish

Greek

Polish

flubendiamid

Swedish

Hungarian

Dutch

Record last updated:	26/01/2021
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