Flamprop-M-isopropyl (Ref: WL 43425)

Flamprop-M-isopropyl (Ref: WL 43425)	Last updated: 02/09/2023
(Also known as: flamprop-M; CL 901444; AC 901444; L-flamprop-isopropyl)

SUMMARY

Flamprop-M-isopropyl is a discontinued herbicide. It has a low solubility in water, is volatile and there is some concern regarding risk of leaching to groundwater. It is moderately persistent in soils. Whilst it has a low mammalian toxicity there is some concern about bioaccumulation. No serious human health risks have been identified. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.

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: GUS: Transition state; Drainflow: Slightly mobile; Potential for particle bound transport: Medium Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute unknown ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Low alert

GENERAL INFORMATION

Description

A translocated, post-emergence arylalanine herbicide used to control wild-oats

Example pests controlled

Avena fatua

Example applications

Wheat

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1978

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Chemical structure

Isomerism

Flamprop-M-isopropyl is the stereospecific ester of the L-isomer of flamprop.

Chemical formula

C₁₉H₁₉ClFNO₃

Canonical SMILES

CC(C)OC(=O)C(C)N(C1=CC(=C(C=C1)F)Cl)C(=O)C2=CC=CC=C2

Isomeric SMILES

C[C@@H](C(=O)OC(C)C)N(C1=CC(=C(C=C1)F)Cl)C(=O)C2=CC=CC=C2

International Chemical Identifier key (InChIKey)

IKVXBIIHQGXQRQ-CYBMUJFWSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H19ClFNO3/c1-12(2)25-19(24)13(3)22(15-9-10-17(21)16(20)11-15)18(23)14-7-5-4-6-8-14/h4-13H,1-3H3/t13-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Arylalanine herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective, systemic, absorbed by leaves

CAS RN

63782-90-1

EC number

618-483-7

CIPAC number

349

US EPA chemical code

PubChem CID

92366

CLP index number

No data found

Molecular mass

363.81

PIN (Preferred Identification Name)

isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate

IUPAC name

isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate

CAS name

1-methylethyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate

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

Avena fatua

Physical state

White crystals

Related substances & organisms

flamprop

flamprop-isopropyl

flamprop-methyl

flamprop-M

Formulations

Property

Value

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

Cyanamid

Example products using this active

Barnon

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

1560000

Acetone

147000

Ethanol

16000

Hexane

500000

Xylene

Melting point (°C)

73.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

4.90 X 10⁰³

Calculated

Log P

3.69

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.32

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

8.50 X 10^-02

Low volatility

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

2.58 X 10^-03

Non-volatile

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

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)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

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

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

750

Notes and range

Best available data

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.96

Calculated

Transition state

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

Value

7.45 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

120

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

flamprop-M

Major fraction

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 4000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

2.5

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Gallus domesticus

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)

1000

Moderate

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

Soil micro-organisms

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)

Moderate

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)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 2.4

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 12

Unknown species

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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)

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

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

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

6.8

Unknown species

Moderate

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

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)

> 4000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Occupational

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause skin damage if contact occurs

Handling issues

Property

Value and interpretation

General

Not expected to autoignite; Not highly flammable

CLP classification 2013

Health: H312
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flamprop-M-isopropyl

French

flamprop isopropyl r-(-)-isomere

German

Flamprop-M-isopropyl

Danish

flamprop-M-isopropyl

Italian

flamprop-isopropile R

Spanish

flamprop-M-isopropil

Greek

Polish

flamprop-M-izopropylu

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	02/09/2023
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