Sulfentrazone (Ref: FMC 97285)

Sulfentrazone (Ref: FMC 97285)	Last updated: 16/08/2021
(Also known as: F6285)

SUMMARY

Sulfentrazone is a herbicide for the control of broad-leaved weeds and some grass species. It has a high aqueous solubility, is volatile and, based on its chemical properties, is mobile with a high potential to leach to groundwater. It can be very persistent in soil and aquatic systems. It is not susceptible to hydrolysis but may degrade via photolysis in aquatic systems. It has a relatively low mammalian toxicity but may bioaccumulate. Whilst its toxicity to birds is relatively low there is greater risk to aquatic species and honey bees.

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; GUS: High leachability; Drainflow: Mobile	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate	Human health Moderate alert: Possible Reproduction/development effects

GENERAL INFORMATION

Description

A herbicide for control of broad-leaved weed and some grasses

Example pests controlled

Carpetweed; Crabgrass; Daisy; Dock; Lambsquarter; Morning glory; Pigweed; Thistles; Waterhemp

Example applications

Soybeans; Chickpeas; Tobacco; Sugarcane; Non-agricultrual areas including highways, roads, fence rows, storage areas, industrial sites

Efficacy & activity

Availability status

Current

Introduction & key dates

1991

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

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

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

Additional information

Also used in

USA

Chemical structure

Isomerism

Chemical formula

C₁₁H₁₀Cl₂F₂N₄O₃S

Canonical SMILES

CC1=NN(C(=O)N1C(F)F)C2=CC(=C(C=C2Cl)Cl)NS(=O)(=O)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OORLZFUTLGXMEF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Aryl triazolinone

Minimum active substance purity

>92.55%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Absorbed by roots and foliage and translocated. Cell membrane disruption - PPO inhibitor.

CAS RN

122836-35-5

EC number

CIPAC number

None allocated

US EPA chemical code

129081

PubChem CID

86369

Molecular mass

387.19

PIN (Preferred Identification Name)

N-{2,4-dichloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]phenyl}methanesulfonamide

IUPAC name

2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide

CAS name

N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide

Other status information

Possible groundwater contaminant

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

Light tan coloured solid forumated as an off-white liquid with faint odour

Related substances & organisms

propylene glycol

Formulations

Property

Value

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

DuPont
FMC Corps

Example products using this active

Authority 480
Sulfentrazone 4F Row

Formulation and application details

Available in a variety of formulations including flowable liquid end-use products and water dispersible granules.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

780

High

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

640000

Acetone

186000

Acetonitrile

66600

Toluene

110

Hexane

Melting point (°C)

122

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

9.79 X 10⁰⁰

Calculated

Log P

0.991

Low

Bulk density (g ml⁻¹)

0.53

Dissociation constant pKa) at 25 °C

6.56

Weak acid

Vapour pressure at 20 °C (mPa)

1.30 X 10^-04

Low volatility

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

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

Max @ 110nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

541

Very persistent

DT₅₀ (lab at 20 °C)

400

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Other sources: DT₅₀ circa 18 months (L3); Other literature 121-302 days (Q3)

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

Stable

Note

Unstable in UV light

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

Value

Stable

Note

Stable under normal environmental conditions

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

Mobile

K_oc

Notes and range

Other sources: 104 mL g⁻¹ (US3, DW3)

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

6.16

Calculated

High leachability

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

Value

2.41 X 10⁰¹

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-hydroxymethyl sulfentrazone (N-(2,4-dichloro-5-(4-(difluoromethyl)-yl)pheny)methanesulfonamide

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2855

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

93.8

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

2.95

Oncorhynchus mykiss

Moderate

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

> 60.4

Daphnia magna

Moderate

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

0.2

Daphnia magna survival

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.800

Americamysis bahia

Moderate

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)

0.29

Lemna gibba

Moderate

Non-target plants

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

32.8

Anabaena flos-aqua

Low

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)

> 25.1

Moderate

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)

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)

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

> 2855

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.13

Rat

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)

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

Moderately toxic through the oral route, less so via dermal exposure
Possible liver and kideny toxicant

Handling issues

Property

Value and interpretation

General

Thermal decomposition and burning may form toxic by-products
Slightly combustible

CLP classification 2013

Health: H332, H373
Environment: H411

EC Risk Classification

Not classified: Obsolete

EC Safety Classification

Not classified: Obsolete

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

sulfentrazone

French

sulfentrazone

German

Sulfentrazon

Danish

sulfentrazon

Italian

sulfentrazone

Spanish

sulfentrazona

Greek

Polish

sulfentrazon

Swedish

Hungarian

Dutch

Record last updated:	16/08/2021
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