Clothianidin (Ref: CGA 322704)

Clothianidin (Ref: CGA 322704)	Last updated: 24/10/2024
(Also known as: Tl 435; HSDB 7281; thiamethoxam metabolite)

SUMMARY

Clothianidin is an insecticide for the control of sucking and chewing pests. It is moderately soluble and volatile but has a high potential for leaching to groundwater. It is very persistent in soil and water. Risk of bioaccumulation is low and its acute toxicity to mammals is considered moderate. It is, however, a neurotoxicant. It is toxic to some aquatic organisms but not greatly so to fish. It is highly toxic to honeybees but low risk to earthworms.

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: Persistent; GUS: High leachability	Ecotoxicity High alert: Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Neurotoxicant

GENERAL INFORMATION

Description

An insecticide used to control sucking and chewing pests on a range of crops including rice, maize and fruit

Example pests controlled

Corn rootworm, Southern corn billbug, Chinch flea beetle, Corn leaf aphid, Cutworms; Seedcorn maggots; Stinkbugs; Thrips; Wireworms; Flea beetles

Example applications

Corn; OSR; Rice; Orchards - apples, apricots, peach, pear, nectarines etc.; Potatoes; Ornamentals; Kohlrabi; Cabbage; Pistachio

Efficacy & activity

Appearance and life cycle

Availability status

Current

Introduction & key dates

2002, introduced

Taxonomic classification

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

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

Denmark/Spain

Date EC 1107/2009 inclusion expires

Not applicable

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

Known to be also used in the following countries

Chemical structure

Isomerism

Isomeric - exists predominantly in the E-form.

Chemical formula

C₆H₈ClN₅O₂S

Canonical SMILES

CN=C(NCC1=CN=C(S1)Cl)N[N+](=O)[O-]

Isomeric SMILES

International Chemical Identifier key (InChIKey)

PGOOBECODWQEAB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)/f/h8,10H/b11-6+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
clothianidin	E-isomer

General status

Biopesticide type

Insecticide, Metabolite, Other substance

Metabolite Type

Soil

Other bioactivity & uses

Biocide, Wood preservative

Substance groups

Neonicotinoid insecticide; Thiazole insecticide; Nitroguanidine insecticide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Translaminar and root systemic activity. Nicotinic acetylcholine receptor (nAChR) channel blocker.

Substance source

Substance production

Uses

Target pests

Target host

Farming system suitability

CAS RN

210880-92-5

EC number

433-460-1

CIPAC number

738

US EPA chemical code

044309

PubChem CID

213027

CLP index number

613-307-00-5

Molecular mass

249.7

PIN (Preferred Identification Name)

(E)-N-[(2-chloro-1,3-thiazol-5-yl)methyl]-N'-methyl-N'-nitroguanidine

IUPAC name

(E)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine

CAS name

(C(E))-N-((2-chloro-5-thiazolyl)methyl)-N'-methyl-N'-nitroguanidine

Other status information

Some applications are approved under GB Biocides Products Regulations; Ban or usage restriction may be in place for use on flowering crops in some Member States

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

Leptinotarsa decemlineata, Myzus persicae

Physical state

White to beige-brownish powder or needles

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

thiamethoxam

Soil

0.356

Major fraction

Formulations

Property

Product

Manufacturer

Example products

Formulation and application details

Usually supplied as a flowable concentrate prepared for uses as a seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

327

Moderate

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

1.04

Heptane

12.8

Xylene

15200

Acetone

2030

Ethyl acetate

Melting point (°C)

176.8

Boiling point (°C)

432.5

Degradation point (°C)

Flashpoint (°C)

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

8.04 X 10⁰⁰

Calculated

Log P

0.905

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.61

Dissociation constant pKa) at 25 °C

11.1

Strong base

Vapour pressure at 20 °C (mPa)

3.8 X 10^-08

Low volatility

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

2.9 X 10^-11

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 solution: 214.5nm = 7770, 265.5nm = 17100, 290nm = 5350

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

545

Very persistent

DT₅₀ (lab at 20 °C)

545

Very persistent

DT₅₀ (field)

121.2

Persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

387

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 143-1001 days, field studies DT₅₀ range 13.3-305.4 days, DT₉₀ range 188- >1000 days; Other studies: field DT₅₀ range 277-1386 days (USA and Canada)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

16.6

Note

Published literature RL₅₀ range 4.4-35.9 days, 3 field crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.1

Fast

Note

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

Value

Stable

Note

Stable pH 4 to pH 9 at 20 °C, hydrolysis occurs in alkali media at elevated temperatures e.g. DT₅₀ 14.4 days at pH 9, 50 °C

Water-sediment DT₅₀ (days)

56.4

Moderately fast

Water phase only DT₅₀ (days)

40.3

Stable

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)

Moderately mobile

K_oc (mL g⁻¹)

123

Notes and range

Freundlich

K_f (mL g⁻¹)

1.48

Moderately mobile

K_foc (mL g⁻¹)

160

¹/_n

0.829

Notes and range

EU dossier K_f range 0.52-4.4 mL g⁻¹, K_foc range 84-345 mL g⁻¹, ¹/_n range 0.809-0.865, Soils=5

pH sensitivity

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

N-(2-chlorothiazol-5-ylmethyl)-N’-nitroguanidine

Minor fraction

0.091

N-methyl-N-nitroguanidine

Major fraction

0.107

N-(2-chlorothiazol-5-ylmethyl)-N-methylurea

Minor fraction

0.044

N-(2-chlorothiazol-5-ylmethyl)-N’-methylguanidine

Minor fraction

nitroguanidine

Minor fraction

0.063

TNG

Minor fraction

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-chlorothiazol-5-ylmethylguanidine

TZG; Thiazolguanidine

Rat

2-Chlorothiazol-5-ylmethylurea

TZU; Thiazolylurea

Rat

nitroguanidine
Note: DT50 soil: 57-95 days; Koc 20.5 days

NTG

Animal; Rat

urea

Rat

formamide

Water

0.160

methylurea

Water

0.11

methylguanidine
Note: Tociologically relvant

a=Water (Photolysis); b=Plants; c=Rat

a=0.350

5-aminomethyl-2-chlorothiazole

ACT

Rat

2-Chlorothiazole-5-carboxylic acid

CTCA

Rat

2-Methylthiothiazole-5-carboxylic acid

MTCA

Rat

N-2-chlorothiazol-5-ylmethyl-N-hydroxy-N’-methyl-N’’-nitroguanidine

THMN; thiazolhydroxymethylnitroguanidine

Rat

N-(2-chlorothiazol-5-ylmethyl)-N’-methylguanidine
Note: Toxicologically relevant; Koc 525-3620 mL/g

TMG; thiazolmethylguanidine

Plants; Sediment; Rat

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 500

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

10.0

Rat

High

(ppm diet)

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

32.7

Unknown species Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

430

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 752 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

56.8

Colinus virginianus NOEC

Moderate

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

13.21

Eisenia foetida

Moderate

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

2.5

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 0.75 kg ha⁻¹

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)

0.044

Apis mellifera

High

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

0.004

Apis mellifera

High

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

Chronic

Bumblebees (Bombus spp.)

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

0.02

Bombus terrestris

High

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)

0.1

Osmia lignaria

High

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

> 8.4

Osmia bicornis

Moderate

Other bee species (1)

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

0.08

Megachile rotundata

High

Mode of exposure

Oral

Other bee species (2)

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

0.014

Andrena prostomias

High

Mode of exposure

Oral 48 hr

Beneficial insects (Ladybirds) as Mortality LC₅₀ g ha⁻¹

> 10

Coccinella septempunctata Larva

Beneficial insects (Lacewings) as % Mortality at dose 60 g ha⁻¹

Chrysoperla carnea Adult

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

1.086

Aphidius rhopalosiphi Adult

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

126.0

Typhlodromus pyri Adult

Beneficial insects (Ground beetles) as % Mortality at dose 462 g ha⁻¹

23.3

Poecilus cupreus Adult

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

> 104.2

Oncorhynchus mykiss

Low

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

20.0

Pimephales promelas

Low

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

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

> 40

Daphnia magna

Moderate

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

0.12

Daphnia magna

Moderate

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

> 100

Ceriodaphnia dubia

Low

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

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

0.029

Chironomus riparius

High

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

0.00072

Chironomus riparius

High

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

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

> 121

Lemna gibba

Low

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

Pseudokirchneriella subcapitata

Low

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

Mesocosm study data

NOEAEC mg l⁻¹

0.0031

Aquatic community

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)

> 500

Rat

Moderate

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.54

Rat

Other Mammal toxicity endpoints

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

0.097

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

0.1

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

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

0.1

Dermal penetration studies (%)

2.25

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

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

Effects consistent with endocrine disruption have been noted in rodents and dogs
May cause hypotension, hypothermia and impaired pupillar function

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. Store at 0-6 DegC

TRANSLATIONS

Language

Name

English

clothianidin

French

clothianidine

German

Clothianidin

Danish

clothianidin

Italian

clotianidin

Spanish

clotianidin

Greek

Polish

chlotianidyna

Swedish

Hungarian

Dutch

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