Flurochloridone (Ref: R 40244)

Flurochloridone (Ref: R 40244)	Last updated: 19/12/2024
(Also known as: fluorchloridone; fluorkloridon; flurocloridona; FLC; fluorochloridone)

SUMMARY

Flurochloridone is a pre-emergence herbicide used to control a range of weeds in umbelliferous crops and other such as cereals and potatoes. It has a low aqueous solubility and is not considered volatile. Under certain conditions it can be persistent in soils but tends not to be in water-sediment systems. Data for human health suggests a low mammalian oral toxicity but there may be risks for reproduction/development and fluorochloridone is classified as a skin sensitiser. With the exception of algae where toxicity is high, toxicity is moderate for most species.

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: Moderately persistent; GUS: Transition state; Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

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, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

No data

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

15/03/2026

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

South Africa

Chemical structure

Isomerism

A molecule with 2 chiral centres, flurochloridone normally refers to a mixture of trans and cis isomers in the ratio 3:1. The trans-isomers have the greater herbicidal activity.

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 groups

Pyrrolidine herbicide; Organochloride herbicide; Organofluoride herbicide

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 - Carotenoid biosynthesis inhibitor.

CAS RN

61213-25-0

EC number

262-661-3

CIPAC number

430

US EPA chemical code

128401

PubChem CID

91677

CLP index number

613-334-00-2

Molecular mass

312.12

PIN (Preferred Identification Name)

mixture of 65–85% rac-(3R,4R)-3-chloro-4-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one and 35–15% rac-(3R,4S)-3-chloro-4-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

IUPAC name

mixture of 65–85% (3RS,4RS)-3-chloro-4-(chloromethyl)-1-(α,α,α-trifluoro-m-tolyl)-2-pyrrolidone and 35–15% (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 Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Beige-peach coloured waxy solid

Related substances & organisms

cis-flurochloridone

trans-flurochloridone

Formulations

Property

Value

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

Agan Chemicals
Syngenta
Makhteshim Agan
Stauffer

Example products using this active

Racer
Rainbow
Ares
Fidelity

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

116000

Methanol

616000

Toluene

Melting point (°C)

40.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

290

Flashpoint (°C)

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

2.29 X 10⁰³

Calculated

Log P

3.36

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal (goats) feeding studies.

Density (g ml⁻¹)

1.19

Dissociation constant pKa) at 25 °C

Not applicable

13.4

Vapour pressure at 20 °C (mPa)

0.27

at 25 °C

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)

2.4 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

6.3

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

6.3

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral soln: 251nm=12700
Acidic soln: 251nm=12800
Alkaline soln: 251nm=12400

Surface tension (mN m⁻¹)

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)

81.4

Moderately persistent

DT₅₀ (field)

40.6

Moderately persistent

DT₉₀ (lab at 20 °C)

283

Persistent

DT₉₀ (field)

240

DT₅₀ modelling endpoint

Note

EU 2021 dossier lab studies DT₅₀ (normalised) range 10.58-11.0 days, field studies DT₅₀ range 39.1-43.9 days; DT₉₀ rate from earlier dossiers.

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

6.48

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)

14.46

Fast

Water phase only DT₅₀ (days)

6.55

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

9.54

Slightly mobile

K_foc (mL g⁻¹)

562

¹/_n

0.923

Notes and range

EU 2021 dossier K_f range 6.52-14.41 mL g⁻¹, K_foc range 487-11240 mL g⁻¹, ¹/_n range 0.882-0.923, 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

2.01

Calculated

Transition state

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

Value

7.75 X 10^-02

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

17.2

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

292

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

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

Minor fraction

0.049

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

Minor fraction

0.030

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

Minor fraction

0.049

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

Minor fraction

0.030

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(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

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

4-dechloro-4-hydroxymethyl

Plant

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

Water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2150

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(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)

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

> 227

Eisenia foetida corr

Moderate

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

Eisenia foetida 8 wk corr

Moderate

Soil micro-organisms

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

Dose: 10 x field rate

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

14.0

Folsomia candida corr

Non-target plants

60.0

Oilseed rape
Vegative vigour, ER₅₀
as g ha⁻¹

11.0

Onion
Seedling emergence, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

100

Apis mellifera

Moderate

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

> 105.9

Apis mellifera

Low

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

Chronic 10d LDD₅₀

> 0.057

Apis mellifera

Notes

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 48 hr

175

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

> 712.2

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)

3.1

Oncorhynchus mykiss

Moderate

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

0.016

Oncorhynchus mykiss

Moderate

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

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

3.5

Daphnia magna

Moderate

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

0.83

Daphnia magna

Moderate

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

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)

0.132

Chironomus riparius as trans isomer

Moderate

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

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

0.015

Lemna gibba

Moderate

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

0.0047

Scenedesmus subspicatus

High

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)

> 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)

0.04

Rat SF=500

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

0.04

Rat SF=500

Dermal penetration studies (%)

1.3-23.8

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

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

>89% of dose eliminated within 72 hrs in urine and faeces

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 or oxisiding
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H317, H360f
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flurochloridone

French

flurochloridone

German

Flurochloridone

Danish

flurochloridon

Italian

flurocloridone

Spanish

flurocloridona

Greek

Polish

flurochloridon

Swedish

Hungarian

fluorkloridon

Dutch

Norwegian

Record last updated:	19/12/2024
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