Flumioxazin (Ref: S 53482)

Flumioxazin (Ref: S 53482)	Last updated: 21/08/2024
(Also known as: flumioxazine)

SUMMARY

A broad-spectrum herbicide. It has a low aqueous solubility, relatively volatile and, based on its chemical properties, the risk of leaching to groundwater is low. It is not usually persistent it either water or soil systems. It has a low mammalian toxicity but a high risk of bioconcentration. There are also risks associated with reproduction/development and flumioxazin is a skin and eye irritant. It is highly toxic to algae and aquatic plants, moderately toxic to earthworms, honeybees, fish and aquatic invertebrates. However, flumioxazin presents less risk to birds.

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: Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A herbicide for pre-emergence broad-spectrum control of weeds particularly in or close to water

Example pests controlled

Eurasian watermilfoil, Curlyleaf pondweed, some species of filamentous algae

Example applications

Soybeans; Peanuts; Vegetables; Fruit; Ornamentals; Forestry; Aquatic areas

Efficacy & activity

Availability status

Current

Introduction & key dates

1994, registered Argentina

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2029

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Czech Republic/France

Date EC 1107/2009 inclusion expires

28/02/2037

EU Candidate for substitution (CfS)

Yes - toxic for reproduction

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

None

Chemical formula

C₁₉H₁₅FN₂O₄

Canonical SMILES

C#CCN1C(=O)COC2=CC(=C(C=C21)N3C(=O)C4=C(C3=O)CCCC4)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

FOUWCSDKDDHKQP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H15FN2O4/c1-2-7-21-15-9-14(13(20)8-16(15)26-10-17(21)23)22-18(24)11-5-3-4-6-12(11)19(22)25/h1,8-9H,3-7,10H2

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flumioxazin	-

General status

Pesticide type

Herbicide

Substance groups

Dicarboximide herbicide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Induces accumulation of porphyrins leading to membrane damage. Inhibition of protoporphyrinogen oxidase (PPO) - cell membrane disruption

CAS RN

103361-09-7

EC number

600-425-7

CIPAC number

578

US EPA chemical code

129034

PubChem CID

92425

CLP index number

613-166-00-X

Molecular mass

354.33

PIN (Preferred Identification Name)

IUPAC name

N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide

CAS name

2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

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

White when pure (99.6%), yellow-brown powder (97.65)

Formulations

Property

Value

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

Interfarm
Sumitomo
Titan Ag Pty Ltd

Example products using this active

Digital
Guillotine
Summimax
Apparent Territory 500WG
Titan

Formulation and application details

Often supplied as a soluble concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.786

Low

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

17000

Acetone

17800

Ethyl acetate

Hexane

1600

Methanol

Melting point (°C)

203.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

273.3

Flashpoint (°C)

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

3.55 X 10⁰²

Calculated

Log P

2.55

Low

Fat solubility of residues

Solubility

Regulatory data

Data type

Density (g ml⁻¹)

1.5

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.32

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)

0.145

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 solution: 215nm = 58211, 289nm = 6748
Acidic solution: 215nm 57861, 289nm = 6736
Basic solution: 220nm = 27512, 299nm = 9781

Surface tension (mN m⁻¹)

70.9

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

21.9

Non-persistent

DT₅₀ (lab at 20 °C)

21.9

Non-persistent

DT₅₀ (field)

17.6

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

58.3

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 11.8-34.7 days, DT₉₀ range 47.7-297 days; Field studies DT₅₀ range 15.6-19.5 days, DT₉₀ range 51.8-64.8 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

Moderately fast

Note

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

Value

Non-persistent

Note

pH sensitive: DT₅₀ at pH 3-5 days; at pH 9 14-23 minutes - all at 25 °C

Water-sediment DT₅₀ (days)

0.4

Fast

Water phase only DT₅₀ (days)

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)

Slightly mobile

K_oc (mL g⁻¹)

889

Notes and range

Other sources: 2240 mL g⁻¹ (DW3)

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.31

Calculated

Low leachability

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

Value

2.59 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

2.26

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)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Insoluble

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

cyclohex-1-ene-1,2-dicarboxylic acid

Minor fraction

0.066

4,5,6,7-tetrahydro-2-benzofuran-1,3-dione

Minor fraction

0.051

6-amino-7-fluoro-4-(2-propynyl)-1,4-benzoxazin-3(2H)-one

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

6-amino-7-fluoro-4-(2-propynyl)-1,4-benzoxazin-3(2H)-one

APF

Water (Hydrolysis)

7-fluoro-5[(2-carboxy-cyclohexenoyl)amino]-4-(2-propynyl)-1,4-benzoxazin-2(2H)-one

482-HA

Surface water (Hydrolysis)

3,4,5,6-tetrahydrophthalic acid anhydride

1-TPA

Water (Hydrolysis)

N-(2-propynyl)-4-[4-carboxy-3-fluoro-2-(3,4,5,6-tetrahydrophthalimido)-2-butenylidene]azetidine-2-one

482-PHO

Water (Photolysis)

disodium cyclohex-1-ene-1,2-dicarboxylate

THPA-2Na

N-(2-propynyl)-4-[4-carboxy-3-fluoro-2-(2-carboxy-1-cyclohexencarbonylamino)-2-butenylidene]azetidine-2-one

PHO-HA

Water

(1S,2S)-2-{[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbamoyl}cyclohexanecarboxylic acid

SAT-482-HA-2

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)

12.7

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 500 ppm

Colinus virginianus

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

34.3

Anas platyrhynchos NOEL

Moderate

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

> 491

Eisenia foetida corr

Moderate

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

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 1.2 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

4.96

Sugar beet
Vegetative vigour, ER₅₀
as g ha⁻¹

14.81

Sugar beet
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)

> 200

Apis mellifera

Low

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

> 229.1

Apis mellifera

Low

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

Chronic

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) as % Mortality at dose 60 g ha⁻¹

Chrysoperla carnea Larva

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

> 600

Aphidius rhopalosiphi

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

> 600

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 0.6 kg ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

2.3

Oncorhynchus mykiss

Moderate

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

0.37

Oncorhynchus mykiss

Moderate

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

2.99

Danio rerio EC₅₀ Embryo

Moderate

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

5.9

Daphnia magna

Moderate

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

0.057

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)

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

0.73

Chironomus riparius

Moderate

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

0.00035

Lemna gibba

High

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

0.000852

Raphidocelis subcapitata

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.93

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.018

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

0.03

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

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

0.022

Dermal penetration studies (%)

2.8-18.5%

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Estimated low risk to bystanders and the public

Occupational

Occupational exposure may occur through dermal and inhalation routes

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Some evidence chronic exposure can cause anaemia

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H360D
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flumioxazin

French

flumioxazine

German

Flumioxazin

Danish

flumioxazin

Italian

flumioxazine

Spanish

flumioxazina

Greek

flumioxazin

Polish

flumioksazyna

Swedish

Hungarian

flumioxazin

Dutch

flumioxazin

Norwegian

Record last updated:	21/08/2024
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