Flumetralin (Ref: CGA 41065)

Flumetralin (Ref: CGA 41065)	Last updated: 24/08/2024
(Also known as: flumethralin)

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; Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

Used to control axillary bud (sucker) growth after the floral portion of tobacco plants have been topped

Example pests controlled

Growth of tobacco suckers

Example applications

Tobacco

Efficacy & activity

Availability status

Introduction & key dates

1983, introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

11/12/2025

UK LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Hungary

Date EC 1107/2009 inclusion expires

11/05/2026

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

Chemical structure

Isomerism

None

Chemical formula

C₁₆H₁₂ClF₄N₃O₄

Canonical SMILES

CCN(CC1=C(C=CC=C1Cl)F)C2=C(C=C(C=C2[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]

Isomeric SMILES

International Chemical Identifier key (InChIKey)

PWNAWOCHVWERAR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H12ClF4N3O4/c1-2-22(8-10-11(17)4-3-5-12(10)18)15-13(23(25)26)6-9(16(19,20)21)7-14(15)24(27)28/h3-7H,2,8H2,1H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flumetralin	-

General status

Pesticide type

Plant Growth Regulator, Herbicide

Substance groups

Unclassified pesticide

Minimum active substance purity

>980 g kg⁻¹

Known relevant impurities

EU dossier: nitrosamine <0.001 g kg⁻¹

Substance origin

Synthetic

Mode of action

Has local systemic effect, contact action, phytotoxic

CAS RN

62924-70-3

EC number

613-108-3

CIPAC number

971

US EPA chemical code

123001

PubChem CID

62210

CLP index number

612-144-00-7

Molecular mass

421.73

PIN (Preferred Identification Name)

N-[(2-chloro-6-fluorophenyl)methyl]-N-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline

IUPAC name

N-(2-chloro-6-fluorobenzyl)-N-ethyl-α,α,α-trifluoro-2,6-dinitro-p-toluidine

CAS name

2-chloro-N-[2,6-dinitro-4-(trifluoromethyl)phenyl]-N-ethyl-6-fluorobenzenemethanamine

Other status information

PAN listed Highly Hazardous Chemical

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)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Yellow crystalline solid

Formulations

Property

Value

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

Syngenta
Trustchem Co. Ltd.

Example products using this active

Prime
Frog
Podos, CGA 41065 150EC

Formulation and application details

Usually supplied as an emulsifiable concentrate and used as a drench

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.01

Low

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

560000

Acetone

18000

Ethanol

14000

n-Hexane

400000

Toluene

Melting point (°C)

104.6

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

195

Flashpoint (°C)

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

3.39 X 10⁰⁵

Calculated

Log P

5.53

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.54

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.720

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)

30.38

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral: 205.5nm=25818
Acidic: 206.9=21487
Basic: 218nm=26919

Surface tension (mN m⁻¹)

72.0

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

727

Very persistent

DT₅₀ (lab at 20 °C)

727

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

2000

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier DT₅₀ range 458-922 days, DT₉₀ >1000 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.25

Fast

Note

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

Value

Stable

Note

Stable at all environmentally relevant pH values

Water-sediment DT₅₀ (days)

13.1

Fast

Water phase only DT₅₀ (days)

1.6

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)

Non-mobile

K_oc (mL g⁻¹)

10000

Notes and range

Freundlich

K_f (mL g⁻¹)

1506

Non-mobile

K_foc (mL g⁻¹)

37068

¹/_n

0.96

Notes and range

EU dossier K_f range 42-8091 mL g⁻¹, K_foc range 8317-80504 mL g⁻¹, ¹/_n range 0.895-1.008, soils=9

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.63

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

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)

676

Whole fish

Threshold for concern

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

2-chloro-6-fluorobenzoic acid (Ref: CGA 152604)

Minor fraction

0.08

N-(2-chloro-6-fluorobenzyl)-2,6-dinitro-4-(trifluoromethyl)aniline (Ref: CGA 146447)

Minor fraction

N2-(2-chloro-6-fluorobenzyl)-N2-ethyl-3-nitro-5-(trifluoromethyl)-1,2-benzenediamine (Ref: CGA 275536)

Minor fraction

2-chloro-6-fluorobenzaldehyde (Ref: SYN 546418)

Minor fraction

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)

2-chloro-6-fluorobenzoic acid (Ref: CGA 152604)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N2-(2-chloro-6-fluorobenzyl)-N2-ethyl-3-nitro-5-(trifluoromethyl)-1,2-benzenediamine

CGA 275536

Sediment; Water

N2-(2-chloro-6-fluorobenzyl)-N2-ethyl-5-(trifluoromethyl)-1,2,3-benzenetriamine

CGA 276432

Water (photolysis); Sediment

1-(2-chloro-6-fluorobenzyl)-2-methyl-5(trifluoromethyl)-7,7a-dihydro-1H-benzimidazol-

SYN 546697

Sediment

2-(2-chloro-6-fluorophenyl)-4-nitro-6-(trifluoromethyl)-3a,4-dihydro-1H-benzimidazole

CGA 288244

Water (photolysis)

2-chloro-4-fluoro-3-[4-nitro-6-(trifluoromethyl)-3a,4-dihydro-1H-benzimidazol-2-yl]phenol

CGA 288244-OH

Water (photolysis)

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)

Rat

(ppm diet)

300

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Coturnix japonica

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)

Eisenia foetida 56 day

Moderate

Soil micro-organisms

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

Dose: 1500 g ha⁻¹ 28 Day

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)

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

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)

Beneficial insects (Lacewings)

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

110.8

Aphidius rhopalosiphi

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

609

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)

0.023

Lepomis macrochirus

High

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

0.00046

Pimephales promelas survival

High

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

> 21.09

Danio rerio Eggs

Moderate

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

> 0.160

Daphnia magna

Moderate

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)

0.094

Mysidopsis bahia

High

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

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

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

3.2

Chironomus riparius

Moderate

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

0.15

Lemna gibba

Moderate

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

0.85

Pseudokirchneriella subcapitata

Moderate

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

0.2

Chlorella pyrenoidosa Growth

Moderate

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.41

Rat

Other Mammal toxicity endpoints

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

0.015

Rat SF=100

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

0.1

Rabbit 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)

0.03

Rabbit SF=303

Dermal penetration studies (%)

0.4-9.0

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Very low risk considering planned uses

Occupational

PPE/PPC recommended

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Possible spleen and liver toxicant

Handling issues

Property

Value and interpretation

General

May expolode if heated in confined space
Demonstrates oxidising properties
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H315, H317, H319
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flumetralin

French

flumetraline

German

Danish

Italian

Spanish

Greek

Polish

flumetralina

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/08/2024
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