Flurochloridone (Ref: R 40244)

Flurochloridone (Ref: R 40244)	Last updated: 28/01/2021
(Also known as: fluorchloridone; fluorkloridon; flurocloridona; FLC; fluorochloridone)

GENERAL INFORMATION

Description

A pre-emergence herbicide used to control a range of weeds in umbelliferous crops, cereals and potatoes

Example pests controlled

Annual broad-leaved weeds; Grasses

Example applications

Cotton; Potatoes; Cereals including winter rye, winter wheat; Sunflowers; Umbelliferous crops including carrot, celery, celeriac, parsnip

Efficacy & activity

Availability status

Current

Introduction & key dates

1985

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

Austria/Hungary

Date EC 1107/2009 inclusion expires

31/05/2021

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

South Africa

Chemical structure

Isomerism

A molecule with 2 chiral centres, flurochloridone normally refers to a 3:1 ratio of trans to cis isomers

Chemical formula

C₁₂H₁₀Cl₂F₃NO

Canonical SMILES

C1C(C(C(=O)N1C2=CC=CC(=C2)C(F)(F)F)Cl)CCl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OQZCSNDVOWYALR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H10Cl2F3NO/c13-5-7-6-18(11(19)10(7)14)9-3-1-2-8(4-9)12(15,16)17/h1-4,7,10H,5-6H2

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flurochloridone	-

General status

Pesticide type

Herbicide

Substance group

Pyrrolidine

Minimum active substance purity

940 g kg⁻¹

Known relevant impurities

EU dossier - Toluene <8.0g kg⁻¹

Substance origin

Synthetic

Mode of action

Selective, absorbed by roots and stem. Bleaching: inhibition of carotenoid biosynthesis.

CAS RN

61213-25-0

EC number

262-661-3

CIPAC number

430

US EPA chemical code

128401

PubChem CID

91677

Molecular mass

312.12

PIN (Preferred Identification Name)

IUPAC name

(3RS,4RS;3RS,4SR)-3-chloro-4-chloromethyl-1-(α,α,α-trifluoro-m-tolyl)-2-pyrrolidone

CAS name

3-chloro-4-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Beige-peach coloured waxy solid

Formulations

Property

Value

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

Racer
Rainbow
Ares
Fidelity

Example products using this active

Agan Chemicals
Syngenta
Makhteshim Agan
Stauffer

Formulation and application details

Often supplied as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

21.9

Low

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

540000

Acetone

592000

Ethyl acetate

326000

Methanol

616000

Toluene

Melting point (°C)

40.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

290

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.29 X 10⁰³

Calculated

Log P

3.36

High

Bulk density (g ml⁻¹)

1.19

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.27

Low volatility

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

2.4 X 10^-03

Non-volatile

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

Maxima at 252nm = 12300

Surface tension (mN m⁻¹)

54.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

40.6

Moderately persistent

DT₉₀ (lab at 20 °C)

283

Persistent

DT₉₀ (field)

240

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 22.8-180 days, DT₉₀ range 51-545 days, field studies DT₅₀ range 11-65 days, DT₉₀ range 75-515 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

6.5

Moderately fast

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

Stable

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

9.4

Slightly mobile

K_foc

700

¹/_n

0.900

Notes and range

EU dossier K_f range 6.5-14.0 mL.g, K_foc range 490-1100 mL g⁻¹, ¹/_n range 0.88-0.91, Soils=4

pH sensitivity

Adsorption increases slighly as pH decreases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.86

Calculated

Transition state

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

Value

6.30 X 10^-02

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

4-chloromethyl-3-hydroxy-1-(3-(trifluoromethyl)phenyl)-2-pyrrolidinona (Ref: R406639)

Soil

0.081

Minor fraction, Relevant

1-(m-trifluoromethylphenyl)-4-chloromethyl-3-pyrrolin-2-one (Ref: R42819)

Soil

0.101

Major, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(4RS)-4-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one (Ref: R42819)
Note: Risk to groundwater

Soil; Groundwater

(4RS)-4-(hydroxymethyl)-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

Water (Photolysis)

(3RS,4RS;3RS,4SR)-3-chloro-4-(hydroxymethyl)-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

4-dechloro-4-hydroxymethyl

Plant

(3RS,4RS,5RS;3RS,4SR,5RS;3RS,4RS,5SR;3RS,4SR,5SR)--3-chloro-4-(chloromethyl)-5-hydroxy-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

5-hydroxy-4-chloromethyl

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

292

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2150

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

> 100

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

590 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

3.0

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.36

Oncorhynchus mykiss 28 day

Moderate

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

3.5

Daphnia magna

Moderate

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

0.83

Daphnia magna

Moderate

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)

> 0.25

Chironomus riparius

Moderate

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

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

0.048

Lemna minor

Moderate

Non-target plants

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

0.0047

Scenedemus subspicatus

High

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

Moderate

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

100

Moderate

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)

> 227

Esenia foetida corr

Moderate

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

Eisenia foetida 8wks

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

1000

48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

1000

7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: -15% effect
Carbon mineralisation: -22% effect

Dose: 10 x field rate

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)

> 2150

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.82

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.04

Rat SF=100

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

0.04

Rat SF=500

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

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

0.04

Rat SF=500

Dermal penetration studies (%)

0.3-4

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified for intended uses
Soil residues may present slight risk to field workers

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

No data found

; ; ; ;

No data found

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 and testes toxicant

Handling issues

Property

Value and interpretation

General

Not explosive

CLP classification 2013

Health: H317, H361
Environment: H400, H410, H411

EC Risk Classification

Reproduction risk category 3: R62/63
Xn - Harmful: R22
N - Dangerous for the environment: R51, R53

EC Safety Classification

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

flurochloridone

French

flurochloridone

German

Flurochloridone

Danish

flurochloridon

Italian

flurocloridone

Spanish

flurocloridona

Greek

Polish

flurochloridon

Swedish

Hungarian

fluorkloridon

Dutch

Record last updated:	28/01/2021
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