Sulfoxaflor (Ref: DE-208)

Sulfoxaflor (Ref: DE-208)	Last updated: 14/03/2021
(Also known as: X11422208; XR-208; XDE-208)

SUMMARY

Sulfoxaflor is a new insecticide that is used to control aphids in field crops and favourably compares with imidacloprid in efficiacy. 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.

GENERAL INFORMATION

Description

Novel 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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

18/08/2025

UK 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
		✓	✓	✓			✓	✓

Also used in

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

No data

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

General status

Pesticide type

Insecticide

Substance group

Sulfoximine

Minimum active substance purity

950g kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

An agonist of n-acetylcholine receptors in insects. Systemic.

CAS RN

946578-00-3

EC number

CIPAC number

820

US EPA chemical code

005210

PubChem CID

16723172

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

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

Example products using this active

Dow AgroSciences

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)

Not expected to self ignite; Not highly flammable

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

6.34 X 10⁰⁰

Calculated

Log P

0.802

Low

Bulk 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)

5.77 X 10^-07

Non-volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.8

Note

Published literature RL₅₀ range 2.3-3.3 days, field grown cucumbers & gojiberries, n=2

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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

0.52

Mobile

K_oc

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

0.47

Mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.983

Major fraction, Relevant

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

Soil

0.122

Major fraction, Relevant

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

Soil

0.092

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

Animals

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)

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 101

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 399

Daphnia magna

Low

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

Daphnia magna

Low

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

Chironmus 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)

Non-target plants

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

> 101

Navicula pelliculose 96hr

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)

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)

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)

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)

0.855

Eisenia foetida

High

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

0.1

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.021

Mortality
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

384.0

Mortality
Typhalosiphi pyri

% Effect

Soil micro-organisms

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

Dose 32mg kg⁻¹ soil 28days

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)

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

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

Possible liver toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H302
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

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Name

English

sulfoxaflor

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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