Thiamethoxam (Ref: CGA 293343)

Thiamethoxam (Ref: CGA 293343)	Last updated: 24/10/2024
(Not known by any other names)

SUMMARY

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: GUS: High leachability; Drainflow: Mobile	Ecotoxicity High alert: Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Possible Carcinogen

GENERAL INFORMATION

Description

A insecticide used to control a wide range of common pests

Example pests controlled

Aphids; Whiteflies; Thrips; Lacewings; Leafhoppers; Mealybugs; Wireworms; Ground beetles; Fire & carpenter ants; Craneflies; Mole crickets

Example applications

Vegetables including brassicas, cucurbits, fruiting vegetables, globe artichoke, leafy vegetables, mint, and root and tuberous vegetables; Turf grass & sod farms; Landscape plants; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1991, discovered; 1997, first registered New Zealand

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France/Spain

Date EC 1107/2009 inclusion expires

Expired

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

Australia, USA, Morocco

Chemical structure

Isomerism

Isomeric - exists in both the E- and Z- forms. Technical product is a mixture.

Chemical formula

C₈H₁₀ClN₅O₃S

Canonical SMILES

CN1COCN(C1=N[N+](=O)[O-])CC2=CN=C(S2)Cl

Isomeric SMILES

CN\1COCN(/C1=N/[N+](=O)[O-])CC2=CN=C(S2)Cl

International Chemical Identifier key (InChIKey)

NWWZPOKUUAIXIW-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
thiamethoxam	-

General status

Pesticide type

Insecticide, Other substance

Other bioactivity & uses

Biocide, Wood preservative

Substance groups

Neonicotinoid insecticide; Nitroguanidine insecticids; Thiazole insecticide; Nitroguanidine neonicotinoid insecticide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Broad spectrum, systemic with contact and stomach action. Nicotinic acetylcholine receptor (nAChR) channel blocker.

CAS RN

153719-23-4

EC number

428-650-4

CIPAC number

637

US EPA chemical code

060109

PubChem CID

5821911

CLP index number

613-267-00-9

Molecular mass

291.71

PIN (Preferred Identification Name)

(4E)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

IUPAC name

(EZ)-3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene(nitro)amine

CAS name

3-((2-chloro-5-thiazolyl)methyl)tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine

Other status information

Some applications may be approved under the GB Biocide Products Regulations; Ban or usage restriction may be in place for use on flowering crops in some EU Member States. Currently being phased out in EU; Chemical subject to PIC regulations: GB Part 2

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

Bemisia tabaci, Leptinotarsa decemlineata, Myzus persicae

Physical state

Crystalline powder

Formulations

Property

Value

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

Syngenta
AgroCare
Kingtai Chemicals
BOC Sciences

Example products using this active

Actara
Cruiser SB
Centric
Flagship
Meridian
Optigard
Platinum

Formulation and application details

Formulations include flowable concentrates for seed treatments, water dispersible granules and suspension concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

4100

High

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

48000

Acetone

7000

Ethyl acetate

Hexane

680

Toluene

Melting point (°C)

139.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

147

Flashpoint (°C)

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

7.41 X 10^-01

Calculated

Log P

-0.13

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.57

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

6.60 X 10^-06

Low volatility

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

4.70 X 10^-10

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

From soil surface

2.1

24 hr

Volatilisation is not considered critical for air pollution

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

255nm = 16800, No absorption maximum between 290nm and 750nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

121

Persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

459

Very persistent

DT₉₀ (field)

296.5

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 34-233 days, DT₉₀ range 114-907 days; field studies DT₅₀ range 7-72 days, DT₉₀ range 23-570 days; Other sources: DT₅₀ range 34-53 days (DW3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

3.2

Note

Tomato leaves, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.4

Note

Published literature RL₅₀ range 1.3-9.1 days, 8 field grown crops, various matrices, n=11

Aqueous photolysis DT₅₀ (days) at pH 7

Value

2.7

Moderately fast

Note

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

Value

Stable

Note

pH sensitive: stable pH 1 to pH 7, DT₅₀ 11.5 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

30.6

Stable

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Mobile

K_oc (mL g⁻¹)

56.2

Notes and range

Other sources: K_oc = 245 mL g⁻¹ (DW3); General literature 70 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.58

Calculated

High leachability

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

Value

5.99 X 10^-01

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

2.5

Calculated using the Atkinson method

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

clothianidin (Ref: CGA 322704)

Major fraction

0.356

Sodium; 5‐(5‐methyl‐4‐nitroimino‐[1,3,5]oxadiazinan‐3‐ylmethyl)‐thiazole‐2‐sulfonate (Ref: NOA 459602)

Sodium; 5‐(N′‐methyl‐N″‐nitro‐guanidinomethyl)‐thiazole‐2‐sulfonate (Ref: SYN 501406)

3‐(2‐Chloro‐thiazol‐5‐ylmethyl)‐5‐methyl‐[1,3,5]oxadiazinan‐4‐one (Ref: CGA 355190)

Major fraction

0.231

Aerobic

3‐(2‐Chlorothiazol‐5‐ylmethyl)‐5‐methyl‐[1,3,5]oxadiazinan‐4‐ylidineamine (Ref: NOA 407475)

Major fraction

0.634

Anaerobic

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 1563

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

576

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 2503 mg kg feed⁻¹

Anas platyrhynchos

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

29.4

Anas platyrhynchos NOEC

Moderate

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

> 1000

Eisenia foetida

Low

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

5.34

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 10 x field rate

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

0.024

Apis mellifera

High

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

0.005

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 48 hrs (range 24-72 hrs) - USEPA data]

Bumblebees (Bombus spp.)

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

0.028

Bombus terrestris

High

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

0.005

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

0.0051

Trigona iridipennnis

High

Mode of exposure

Contact

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

0.004

Nannotrigona perilampoides

High

Mode of exposure

Contact

Beneficial insects (Ladybirds) as Mortality LC₅₀ mg l⁻¹

> 4.85

Coccinella septempunctata Larva

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as % Mortality at dose 0.2 kg ha⁻¹

100

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as % Mortality at dose 0.2 kg ha⁻¹

100

Typhlodromus pyri Protonymph

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)

> 125

Oncorhynchus mykiss

Low

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

Oncorhynchus mykiss 88 day

Low

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

21.8

Danio rerio EC₅₀ Embryo

Moderate

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

> 100

Daphnia magna

Low

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

> 100

Daphnia magna

Low

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

> 80

Ceriodaphnia dubia

Moderate

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

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

0.0553

Chironomus dilutus

High

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.01

Chironomus riparius

Moderate

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

0.10

Chironomus riparius

Moderate

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

> 90

Lemna gibba 7 day

Low

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

> 100

Pseudokirchneriella subcapitata

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)

> 1563

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.72

Rat

Other Mammal toxicity endpoints

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

0.026

Mouse SF=100

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

0.5

Rabbit 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)

0.08

Dog SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Increased incidence of liver cell adenoma and adenocarcinoma in mice
US EPA - likely to be human carcinogen

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H302
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Limited shelf-life.

TRANSLATIONS

Language

Name

English

thiamethoxam

French

thiamethoxam

German

Thiamethoxam

Danish

thiamethoxam

Italian

tiametoxam

Spanish

tiametoxam

Greek

Polish

tiametoksam

Swedish

tiametoxam

Hungarian

tiametoxam

Dutch

thiamethoxam

Norwegian

Record last updated:	24/10/2024
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