Flazasulfuron (Ref: OK 1166)

Flazasulfuron (Ref: OK 1166)	Last updated: 23/01/2021
(Also known as: SL 160)

GENERAL INFORMATION

Description

A pre- and post-emergence selective herbicide used to control a wide range of annual and perennial weeds

Example pests controlled

Grasses, Broad-leaved weeds, Sedges

Example applications

Turf; Citrus; Grapes; Olives; Sugarcane; Non-cropped areas

Efficacy & activity

Efficacy has been scientifically donstrated. Many crops show very good tolerance as long as green parts are not exposed.

Availability status

Current

Introduction & key dates

1989, Japan

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2032

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/France

Date EC 1107/2009 inclusion expires

31/01/2032

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, Brazil, Colombia, Mexico, Japan, Taiwan

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₁₂F₃N₅O₅S

Canonical SMILES

COC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)C2=C(C=CC=N2)C(F)(F)F)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

HWATZEJQIXKWQS-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H12F3N5O5S/c1-25-8-6-9(26-2)19-11(18-8)20-12(22)21-27(23,24)10-7(13(14,15)16)4-3-5-17-10/h3-6H,1-2H3,(H2,18,19,20,21,22)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, absorbed through leaves. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

104040-78-0

EC number

CIPAC number

595

US EPA chemical code

119011

PubChem CID

93539

Molecular mass

407.37

PIN (Preferred Identification Name)

N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-3-(trifluoromethyl)pyridine-2-sulfonamide

IUPAC name

1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)urea

CAS name

N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(trifluoromethyl)-2-pyridinesulfonamide

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

White crystalline powder

Formulations

Property

Value

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

Mission
Aikido
Chikara
Epsilon
Katana
Paradise

Example products using this active

ISK Biosciences
Ishihara Sangyo Kaisha Ltd.
Belchim

Formulation and application details

Usually supplied as a wettable powder.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2100

High

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

0.5

n-Hexane

560

Toluene

22100

Dichloromethane

6900

Ethyl acetate

Melting point (°C)

180

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

181.5

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

8.71 X 10^-01

Calculated

Log P

-0.06

Low

Bulk density (g ml⁻¹)

1.62

Dissociation constant pKa) at 25 °C

4.37

Weak acid

Vapour pressure at 20 °C (mPa)

0.0133

Low volatility

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

2.58 X 10^-06

Non-volatile

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

241.0nm = 17300

Surface tension (mN m⁻¹)

70.5

at 20 °C 100%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

41.2

Moderately persistent

DT₅₀ (lab at 20 °C)

41.2

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

162.3

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2016 dossier lab studies DT₅₀ range 7.65-102.1 days, DT₉₀ range 55.5-339.3 days, field studies DT₅₀ range 2-18 days, DT₉₀ range 10-100 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

Stable

Note

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

Value

Non-persistent

Note

pH sensitive: DT₅₀ 0.5 days at pH 4, 2.6 days at pH 5, 8.8 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Mobile

K_oc

46.2

Notes and range

EU dossier K_oc range 32.4-80.9 mL g⁻¹, Soils=4

Freundlich

K_f

4.79

Moderately mobile

K_foc

283.3

¹/_n

0.844

Notes and range

EU 2016 dossier K_f range 1.87-8.45 mL g⁻¹, K_foc range 59-768 mL g⁻¹, ¹/_n range 0.80-0.87, Soils=4

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.55

Calculated

Low leachability

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

Value

2.32 X 10^-02

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

1-(4,6-dimethoxypyrimidin-2-yl)-1-(3-trifluoromethyl-2-pyridyl)urea

Soil

0.663

Major fraction, Relevant

3-trifluoromethyl-2-pyridylsulfonamide

Soil

0.260

Major fraction, Relevant

4,6-dimethoxy-N-(3-(trifluoromethyl)pyridin-2-yl)pyrimidin-2-amine

Soil

0.478

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4,6-dimethoxy-2-pyrimidinamine
Note: Oral LD50(rat) = 737mg/kg

ADMP

Mammal; Plant; Soil; groundwater

6-Methoxy-2-{[3-(trifluoromethyl)pyridin-2-yl]amino}pyrimidin-4-ol

HTPP

Water; Sediment; Soil

1-(4,6-Dimethoxypyrimidin-2-yl)urea

DMPU

Mammal; Plant; Soil (photolysis); Surface water; groundwater

N-[(4-Methoxy-6-oxo-1,6-dihydropyrimidin-2-yl)carbamoyl]-3-(trifluoromethyl)pyridine-2-sulfonamide

HMTU

Groundwater; Mammal; Soil

1-(4-Hydroxy-6-methoxypyrimidin-2-yl)-1-[3-(trifluoromethyl)pyridin-2-yl]urea

HTPU

Mammal; Soil; Surface water

3-(Trifluoromethyl)pyridin-2(1H)-one

HTF

Groundwater; Soil (photolysis); Surface water; Groundwater

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)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

11.7

Rat

High

(ppm diet)

200

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

11.7

Rat Reproduction

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

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

> 100

Colinus virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

Oncorhynchus mykiss

Moderate

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

> 25

Daphnia magna

Moderate

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

6.25

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)

0.1

Chironomus riparius

Moderate

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

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

0.00004

Lemna gibba 7 day

High

Non-target plants

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

0.014

Pseudokirchneriella subcapitata

Moderate

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

0.005

Pseudokirchneriella subcapitata

Moderate

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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)

> 100

Bombus terrestris

Low

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

97.5

Bombus terrestris

Moderate

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)

> 15.75

Moderate

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

8.0

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

125

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality / Reproduction [Dose: 0.05 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Beneficial capacity [Dose: 0.02 kg ha⁻¹]
Typhlodromus pyri adult

Soil micro-organisms

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

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.99

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.013

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

None allocated

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

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

0.02

Dog 1 year SF=100

Dermal penetration studies (%)

10.0

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible Liver, kidney & blood toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

flazasulfuron

French

flazasulfuron

German

Flazasulfuron

Danish

flazasulfuron

Italian

flazasulfuron

Spanish

flazasulfuron

Greek

Polish

flazasulfuron

Swedish

Hungarian

flazaszulfuron

Dutch

flazasulfuron

Record last updated:	23/01/2021
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