Clothianidin (Ref: CGA 322704)

Clothianidin (Ref: CGA 322704)	Last updated: 11/01/2021
(Also known as: Tl 435; HSDB 7281; thiamethoxam metabolite)

SUMMARY

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

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

Efficacy & activity

Availability status

Current

Introduction & key dates

2002

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

None

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
		✓	✓		✓

Also used in

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

No data

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

Pesticide type

Insecticide, Metabolite

Metabolite Type

Soil

Substance group

Neonicotinoid

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. Acetylcholine receptor (nAChR) agonist.

CAS RN

210880-92-5

EC number

CIPAC number

738

US EPA chemical code

044309

PubChem CID

213027

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

NOTE ban or usage restriction may be in place for use on flowering crops in some Member States

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

Leptinotarsa decemlineata, Myzus persicae

Physical state

Colourless powder

Related substances & organisms

beta-cyfluthrin

prothioconazole

tebuconazole

triazoxide

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

thiamethoxam

Soil

0.356

Major fraction, Relevant

Formulations

Property

Value

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

Deter
Modesto
Poncho
Belay

Example products using this active

Bayer CropScience
Sumitomo Chemical Co
Takeda Chemicals

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)

340

pH 10

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)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

8.04 X 10⁰⁰

Calculated

Log P

0.905

Low

Bulk density (g ml⁻¹)

1.61

Dissociation constant pKa) at 25 °C

11.1

Strong base

Vapour pressure at 20 °C (mPa)

2.8 X 10^-08

Low volatility

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

2.9 X 10^-11

Non-volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

123

Notes and range

Freundlich

K_f

1.48

Moderately mobile

K_foc

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

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.74

Calculated

High leachability

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

Value

9.02 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.091

Minor fraction, Relevant

N-methyl-N-nitroguanidine

Soil

0.107

Major fraction, Relevant

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

Soil (photolysis)

0.044

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

TMG; thiazolmethylguanidine

Soil; Plants; Sediment; Rat

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

NTG

a=Soil; b=Animal; c=Rat

a:0.063

formamide

Water

0.160

methylurea

Water

0.11

-
Note: Koc 13.8-17.3 mL/g

TNG

Soil

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

2-chlorothiazol-5-ylmethylguanidine

TZG; Thiazolguanidine

Rat

2-Chlorothiazol-5-ylmethylurea

TZU; Thiazolylurea

Rat

urea

Rat

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)

> 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

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 104.2

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

20.0

Pimephales promelas

Low

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

> 40

Daphnia magna

Moderate

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

0.12

Daphnia magna

Moderate

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

Non-target plants

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

Pseudokirchneriella subcapitata

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)

0.044

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)

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 pollinators (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 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)

13.21

Eisenia foetida

Moderate

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

2.5

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 0.06 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

96.7

Mortality [Dose: 0.06 kg ha⁻¹]
Typhlodromus pyri adult

Soil micro-organisms

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

Dose: 0.75 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

0.0031

Aquatic community

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)

> 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

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)

0.1

Rat ASF=100

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

CLP classification 2013

Health: H302
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S46, S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

clothianidin

French

clothianidine

German

Clothianidin

Danish

clothianidin

Italian

clotianidin

Spanish

clotianidin

Greek

Polish

chlotianidyna

Swedish

Hungarian

Dutch

Record last updated:	11/01/2021
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