Sulfoxaflor (Ref: DE-208)

Sulfoxaflor (Ref: DE-208)	Last updated: 20/11/2024
(Also known as: X11422208; XR 208; XDE 208)

SUMMARY

Sulfoxaflor is an insecticide that is used to control aphids in field crops and favourably compares with imidacloprid in efficacy. It is relatively volatile, whilst potentially mobile in soils it has a low potential for leaching due to its rapid degradation rate. It has a high potential to bioaccumulate, generally moderately toxic to birds and mammals and has a low toxicity to most aquatic species. It is toxic to honeybees and earthworms. No serious human health risks have been identified.

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: Drainflow: Mobile	Ecotoxicity High alert: Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High; Earthworms acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A substance for the control of aphids in field and agricultural crops

Example pests controlled

Aphids

Example applications

Tomatoes; Peppers; Aubergines; Cucumbers; Melons; Courgettes; Cereals including wheat, rye, barley, oats, triticale; Cotton

Efficacy & activity

Availability status

Current

Introduction & key dates

2007, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

18/08/2031

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Ireland

Date EC 1107/2009 inclusion expires

18/08/2025

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
		✓	✓	✓	✓		✓	✓

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

Morocco

Chemical structure

Isomerism

Sulfoxaflor is a chiral molecule. The technical material is a mixture of four diastereoisomers arising from the molecules two tetrahedral stereocentres.

Chemical formula

C₁₀H₁₀F₃N₃OS

Canonical SMILES

CC(C1=CN=C(C=C1)C(F)(F)F)S(=NC#N)(=O)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

ZVQOOHYFBIDMTQ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H10F3N3OS/c1-7(18(2,17)16-6-14)8-3-4-9(15-5-8)10(11,12)13/h3-5,7H,1-2H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
(-)-(2R,3R)-sulfoxaflor	Isomer
(+)-(2S,3S)-sulfoxaflor	Isomer

General status

Pesticide type

Insecticide

Substance groups

Sulfoximine insecticide

Minimum active substance purity

950g kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

Systemic. Nicotinic acetylcholine receptor (nAChR) channel blocker.

CAS RN

946578-00-3

EC number

807-366-8

CIPAC number

820

US EPA chemical code

005210

PubChem CID

16723172

CLP index number

616-217-00-4

Molecular mass

277.27

PIN (Preferred Identification Name)

[(E)-methyl(oxo){(1E)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-γ6-sulfanylidene]cyanamide

IUPAC name

[methyl(oxo){1-[6-(trifluoromethyl)-3-pyridyl]ethyl}-γ6-sulfanylidene]cyanamide

CAS name

N-(methyloxido(1-(6-(trifluoromethyl)-3-pyridinyl)ethyl)-γ4-sulfanylidene)cyanamide

Other status information

PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

None identified

Physical state

White powder with acidic odour

Formulations

Property

Value

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

Dow AgroSciences

Example products using this active

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

568

High

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

0.242

n-Heptane

0.743

Xylene

39600

1,2-Dichloroethane

93100

Methanol

Melting point (°C)

112.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

167.7

Flashpoint (°C)

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

6.34 X 10⁰⁰

Calculated

Log P

0.802

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.519

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.4 X 10^-03

Low volatility

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

6.83 X 10^-07

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral soln: max at 197, 201, 260nm
Acidic soln: max at 203,209 260nm
Basic soln: max at 217m 260nm

Surface tension (mN m⁻¹)

57.5

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

2.2

Non-persistent

DT₅₀ (lab at 20 °C)

2.2

Non-persistent

DT₅₀ (field)

3.54

Non-persistent

DT₉₀ (lab at 20 °C)

21.5

Non-persistent

DT₉₀ (field)

11.74

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.041-12.9 days, DT₉₀ range 0.14-127 days; Field studies DT₅₀ range 1.46-7.43 days, DT₉₀ range 4.84-24.68 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.2

Note

Published literature RL₅₀ range 1.3-3.3 days, field grown fennel, cucumbers & gojiberries, n=4

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)

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

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

0.52

Mobile

K_oc (mL g⁻¹)

40.8

Notes and range

EU dossier K_d range 0.22-1.37 mL g⁻¹, K_oc range 13-76 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

0.47

Mobile

K_foc (mL g⁻¹)

¹/_n

0.96

Notes and range

EU dossier K_f range 0.16-1.28 mL g⁻¹, K_foc range 12-71 mL.g, ¹/_n range 0.964-1.000

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.35

Calculated

Low leachability

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

Value

3.06 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

15.53

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)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

N-(methyl(oxido)(1-(6-trifluoromethyl)pyridine-3-yl)ethyl)-Lambda-4-sulfanylidene)urea (Ref: X11719474)

Major fraction

0.986

5-(1-methyanesulfonyl-ethyl)-2-trifluoromethyl-pyridine (Ref: X11519540)

Major fraction

0.109

5-(1-(S-methylsulfonimidoyl)ethyl)-2-(trifluoromethyl)pyridine (Ref: X11579457)

Minor fraction

0.085

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

5-(1-(S-methylsulfonimidoyl)ethyl)-2-(trifluoromethyl)pyridine (Ref: X11579457)

Not relevant

5-(1-methyanesulfonyl-ethyl)-2-trifluoromethyl-pyridine (Ref: X11519540)

Not relevant

N-(methyl(oxido)(1-(6-trifluoromethyl)pyridine-3-yl)ethyl)-Lambda-4-sulfanylidene)urea (Ref: X11719474)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

1-(6-(trifluoromethyl)pyridin-3-yl)ethanol (Ref: X11721061)

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1000

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

676

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 ppm

Colinus virginianus

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

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

0.855

Eisenia foetida

High

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

0.10

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose 32 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

0.08

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

0.379

Apis mellifera

High

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

0.146

Apis mellifera

High

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

Chronic

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 3 hrs - USEPA data]

Bumblebees (Bombus spp.)

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

7.55

Bombus terrestris

Moderate

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

0.027

Bombus terrestris

High

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)

>= 0.0055

Osmia bicornis

High

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 LR₅₀ g ha⁻¹

> 48

Chrysoperla carnea

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

0.021

Aphidius rhopalosiphi

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

384.0

Typhalosiphi pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

> 101

Oncorhynchus mykiss

Low

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

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

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

> 399

Daphnia magna

Low

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

Daphnia magna

Low

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

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

0.643

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.622

Chironomus dilutus

Moderate

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)

> 101

Navicula pelliculosa 96hr

Low

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)

1000

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.09

Rat

Other Mammal toxicity endpoints

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

0.04

Rat SF=100

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

0.25

Rat SF=100

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

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

0.06

Rat SF=100

Dermal penetration studies (%)

0.08-6%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk for prescribed uses

Occupational

Low risk for prescribed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL modified for some crops October 2024. Consult register.

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant
US EPA - weak evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302
Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

sulfoxaflor

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	20/11/2024
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