Tolclofos-methyl (Ref: S 3349 )

Tolclofos-methyl (Ref: S 3349 )	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A fungicide seed treatment for soil-borne and seed-borne diseases

Example pests controlled

Seedling blight; Seed decay; Damping-off; Stem canker; Black scurf

Example applications

Potatoes; Lettuce; Soybean; Field corn; Sweetcorn; Popcorn; Cotton; Sorghum; Sugarbeet; Ornamentals

Efficacy & activity

Efficiacy established from field trials and long term use in the EU

Availability status

Current

Introduction & key dates

1982, Japan

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/Denmark

Date EC 1107/2009 inclusion expires

31/08/2034

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

Australia

Chemical structure

Isomerism

Chemical formula

C₉H₁₁Cl₂O₃PS

Canonical SMILES

CC1=CC(=C(C(=C1)Cl)OP(=S)(OC)OC)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OBZIQQJJIKNWNO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H11Cl2O3PS/c1-6-4-7(10)9(8(11)5-6)14-15(16,12-2)13-3/h4-5H,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Chlorophenyl

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU 2018 dossier - methanol 1 g kg⁻¹

Substance origin

Synthetic

Mode of action

Nonsystemic with contact action showing protective and curative properties. Lipid peroxidation inhibitor.

CAS RN

57018-04-9

EC number

260-515-3

CIPAC number

479

US EPA chemical code

128905

PubChem CID

91664

Molecular mass

301.13

PIN (Preferred Identification Name)

O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl phosphorothioate

IUPAC name

O-2,6-dichloro-p-tolyl O,O-dimethyl phosphorothioate

CAS name

O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl phosphorothioate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

Colourless crystalline powder

Related substances & organisms

thiram

Formulations

Property

Value

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

Rizolex
Rizolex Flowable
Agrolex
Hektolex
Risolex

Example products using this active

Certis
Scotts
FCC
King Tech Corp
Interfarm
Sumitomo

Formulation and application details

Available in a variety of formulations including wettable powders, flowable concentrates and dry powders for seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.708

Low

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

476000

Acetone

343000

Xylene

20000

n-Hexane

38000

Methanol

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

120

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

6.31 X 10⁰³

Calculated

Log P

3.8

High

Bulk density (g ml⁻¹)

1.52

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.877

Low volatility

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

3.70 X 10^-01

Moderately volatile

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

pH 7.2: 215.5nm = 2380, 275nm = 484, 282.5nm = 511

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

7.6

Non-persistent

DT₅₀ (lab at 20 °C)

7.6

Non-persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

48.0

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

31.0

worse case un-normalised lab study

Note

EU 2018 dossier lab studies DT₅₀ range 2.1-16.4 days, DT₉₀ range 6.8-102.9 days, Soils=12

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

6.7

Note

Published literature RL₅₀ range 2.5-10.8 days, 2 field & undercover grown crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

38.3

Stable

Note

Data for November sunlight 40 deg N

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

Value

Moderately persistent

Note

pH sensitive: DT₅₀ 126 days at pH 4, 102 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

1.25

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

21.8

Slightly mobile

K_foc

3028

¹/_n

0.93

Notes and range

EU 2018 dossier K_f range 7.60-320 mL g⁻¹, K_foc range 1649-6139 mL g⁻¹, ¹/_n range 0.89-0.96, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.77

Calculated

Low leachability

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

Value

1.42 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

O-(2,6-dichloro-4-methylphenyl) O-methyl O-hydrogen phosphorothioate

Soil

0.133

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

hydroxmethyl-tolclofos-methyl

TM-CH2OH

Plant

3,5-dichloro-4-hydroxybenzoic acid

Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

670

Threshold for concern

CT₅₀ (days)

1.1

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 70.6

Rat

High

(ppm diet)

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

≥ 668

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Anas platyrhynchos

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

Anas platyrhynchos NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.69

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.012

Oncorhynchus mykiss

Moderate

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

Daphnia magna

Moderate

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

0.026

Daphnia magna

Moderate

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

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

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)

0.78

Scenedemus subspicatus

Moderate

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

0.032

Unknown species

Moderate

Honeybees (Apis spp.)

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

> 100

Low

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

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)

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)

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)

> 500

Eisenia foetida corr

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

43.7

48 hour
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

25000

7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 18.8 kg ha⁻¹

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.07

Rat (nose only)

Other Mammal toxicity endpoints

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

0.064

Mouse SF=100

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

0.14

Mouse SF=100

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

0.14

Mouse SF=100

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

0.064

Mouse SF=100

Dermal penetration studies (%)

0.02-6.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

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

General human health issues

Endocrine issues - Competitive binding to cellular estrogen receptors
Possible liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S24, S37, S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Variable with product, usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

tolclofos-methyl

French

tolclofos-methyle

German

Tolclofos-methyl

Danish

tolclofos-methyl

Italian

tolclofos-metile

Spanish

tolclofos-metil

Greek

Polish

tolchlofos metylowy

Swedish

tolklofosmetyl

Hungarian

Dutch

tolclofos-methyl

Record last updated:	12/01/2021
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