Sulcotrione (Ref: SC 0051)

Sulcotrione (Ref: SC 0051)	Last updated: 14/03/2021
(Also known as: sulcotrion; ICI A0051)

GENERAL INFORMATION

Description

A herbicide for grass and broad-leaved weed control in maize, sugar cane and other crops

Example pests controlled

Pigweed; Goosefoot; Crabgrass; Common purslane; khaki weed; Bladder weed; Italian ryegrass; Dwarf marigold; Nightshade

Example applications

Maize; Sweetcorn; Sorghum; Sunflowers; Soybean; Cotton; Wheat; Broccoli; Carrots; Curcubits; Tobacco

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

Approved

Dossier rapporteur/co-rapporteur

Germany/Spain

Date EC 1107/2009 inclusion expires

31/08/2022

EU Candidate for substitution (CfS)

Yes - low ADI / ARfD / AOEL

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

Chemical structure

Isomerism

Chemical formula

C₁₄H₁₃ClO₅S

Canonical SMILES

CS(=O)(=O)C1=CC(=C(C=C1)C(=O)C2C(=O)CCCC2=O)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

PQTBTIFWAXVEPB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H13ClO5S/c1-21(19,20)8-5-6-9(10(15)7-8)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Triketone

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - hydrogen cyanide 80mg kg⁻¹, toluene 4g kg⁻¹

Substance origin

Synthetic

Mode of action

Absorbed mainly by the leaves but also some root uptake. Bleaching: inhibition of 4-hydroxyphenyl-pyruvate-dioxygenase.

CAS RN

99105-77-8

EC number

CIPAC number

723

US EPA chemical code

PubChem CID

91760

Molecular mass

328.77

PIN (Preferred Identification Name)

2-[2-chloro-4-(methanesulfonyl)benzoyl]cyclohexane-1,3-dione

IUPAC name

2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione

CAS name

2-[2-chloro-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione

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 solid

Formulations

Property

Value

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

Mikado
Cyclone

Example products using this active

Syngenta

Formulation and application details

Usually supplied as a suspension concentrate that 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)

165.0

Moderate

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

2000

Xylene

190000

Dichloromethane

48000

Acetone

300

1-Octanol

Melting point (°C)

139

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

170

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10^-02

Calculated

Log P

-1.7

Low

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

3.13

Weak acid

Vapour pressure at 20 °C (mPa)

5.00 X 10^-03

Low volatility

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

6.0 X 10^-07

Non-volatile

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

285nm = 15239, 283.5nm = 16868, 259 nm = 20364

Surface tension (mN m⁻¹)

69.0

at 20°C 90% soln

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

25.3

Non-persistent

DT₅₀ (field)

3.6

Non-persistent

DT₉₀ (lab at 20 °C)

100.2

Persistent

DT₉₀ (field)

18.4

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 10.8-89.7 days, DT₉₀ range 47-246 days; field studies DT₅₀ range 1.2-11.4 days, DT₉₀ range 6.9-38 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

25.6

Slow

Note

pH sensitive: DT₅₀ 13 days at pH 4, 40.9 days at pH 9, all data for 5 cm depth and seasonal mean values. Degradation slower at 30 cm depth.

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

Value

Stable

Note

Stable at pH 5 to pH 9, temp 25-40 °C

Water-sediment DT₅₀ (days)

63.9

Moderately fast

Water phase only DT₅₀ (days)

9.5

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

1.05

Mobile

K_foc

¹/_n

0.839

Notes and range

EU dossier K_f range 0.29-2.26, K_foc range 17-58 mL g⁻¹, ¹/_n range 0.812-0.888, Soils=6

pH sensitivity

Predominantly OC-dependent but pH-dependent to a minor extent

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.36

Calculated

Low leachability

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

Value

3.10 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-chloro-4-methylsulfonyl-benzoic acid

Soil

0.603

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-hydroxyphenyl pyruvate

Rat (Blood)

4-hydroxy-sulcotrione, 2-[2-chloro-4-(methylsulfonyl)benzoyl]-4-hydroxycyclohexane-1,3-dione

sulcotrione metabolite M02

Rat (Urinary)

5-hydroxy-sulcotrione, 2-[2-chloro-4-(methylsulfonyl)benzoyl]-5-hydroxycyclohexane-1,3-dione

sulcotrione metabolite M04

Rat (Urinary)

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)

> 0.5

Rat 2 year

High

(ppm diet)

> 100

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1350

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1259 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

227

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

3.2

Oncorhynchus mykiss Juvenile growth

Moderate

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

> 848

Daphnia magna

Low

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

> 75

Daphnia magna

Low

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)

0.051

Lemna gibba

Moderate

Non-target plants

7.0

Lactuca sativa
Seedling emergence, ER₅₀
as g ha⁻¹

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

1.2

Raphidocelis subcapitata

Moderate

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)

200

Low

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

Moderate

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)

> 1000

Low

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

450

>, 48 hour
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

450

>, 7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 4.5 kg ha⁻¹ 28 days

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)

4000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.63

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.0004

Rat SF=100

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)

0.0006

Rat SF=100

Dermal penetration studies (%)

0.1-0.5

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified for intended use

Occupational

No unacceptable risks to operators or other workers identified for intended use

MRLs

European

EU MRL pesticide database

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Potential kidney and liver toxicant
May cause eye damage

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317, H361d, H373
Environment: H400, H410

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R43

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

sulcotrione

French

sulcotrione

German

Sulcotrion

Danish

sulcotrion

Italian

sulcotrione

Spanish

sulcotriona

Greek

Polish

sulkotrion

Swedish

Hungarian

Dutch

sulcotrion

Record last updated:	14/03/2021
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