Metyltetraprole (Ref: S-2367)

Metyltetraprole (Ref: S-2367)	Last updated: 24/01/2023
(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: Persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High	Human health Moderate alert: Possible Carcinogen; Possible Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

A fungicide that is highly effective against a wide range of fungal diseases in cereals and other crops

Example pests controlled

Ascomycetes spp.; Septoria diseases

Example applications

Cereals; Sugar beet; Root crops; Pulses; Oilseeds; Leafy crops

Efficacy & activity

Efficacy demonstrated on various representative uses

Availability status

Novel

Introduction & key dates

2018

UK regulatory status

UK COPR regulatory status

Pending

Date COPR inclusion expires

UK LERAP status

No UK approval for use.

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Pending

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

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

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₉H₁₇ClN₆O₂

Canonical SMILES

CC1=C(C(=CC=C1)N2C(=O)N(N=N2)C)COC3=NN(C=C3)C4=CC=C(C=C4)Cl

Isomeric SMILES

Not applicable

International Chemical Identifier key (InChIKey)

XUQQRGKFXLAPNV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H17ClN6O2/c1-13-4-3-5-17(26-19(27)24(2)22-23-26)16(13)12-28-18-10-11-25(21-18)15-8-6-14(20)7-9-15/h3-11H,12H2,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Tetrazole fungicide; Phenylpyrazole fungicide

Minimum active substance purity

<935 g kg⁻¹

Known relevant impurities

Substance origin

Synthetic

Mode of action

Quinone Outside Inhibitor (QoI). Thought to inhibit the respiratory chain via complex III although it remains effective against QoI resistant strains

CAS RN

1472649-01-6

EC number

No data found

CIPAC number

None allocated

US EPA chemical code

PubChem CID

8988183

CLP index number

No data found

Molecular mass

396.83

PIN (Preferred Identification Name)

1-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]-3-methylphenyl]-1,4-dihydro-4-methyl-5H-tetrazol-5-one

IUPAC name

1-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]-3-methylphenyl]-1,4-dihydro-4-methyl-5H-tetrazol-5-one

CAS name

5H-Tetrazol-5-one, 1-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]-3-methylphenyl]-1,4-dihydro- 4-methyl-

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)

11A

Examples of recorded resistance

None identified

Physical state

White powder without odour

Formulations

Property

Value

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

Sumitomo
BASF

Example products using this active

Pavecto

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.12

Low

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

7400

Methanol

86000

Acetone

48000

Ethyl Acetate

37000

Toluene

Melting point (°C)

130

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

275

Flashpoint (°C)

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

1.45 X 10⁰⁴

Calculated

Log P

4.16

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

No dissociation

Vapour pressure at 20 °C (mPa)

8.9 X 10^-05

Low volatility

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

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

Acidic soln: 213nm=23500, 275nm=24100
Neutral soln: 214nm=22500, 275nm=23700
Alkaline soln: 275nm=23800

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)

1000

Very persistent

DT₅₀ (lab at 20 °C)

1000

Very persistent

DT₅₀ (field)

320

Persistent

DT₉₀ (lab at 20 °C)

2000

Very persistent

DT₉₀ (field)

1732

DT₅₀ modelling endpoint

Note

EU dossier (2022) DT₅₀ lab studies (normalised) range 703 to >1000 days, Soils=6; DT₉₀ (measured) >1000 days, Soils=6; Field studies DT₅₀ (normalised) range 242-397 days, Soils= 4, DT₉₀ (measured) range 703-2680 days, Soils =4

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

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 at all relevant pH values up to 50 °C

Water-sediment DT₅₀ (days)

553

Stable

Water phase only DT₅₀ (days)

1.5

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

74.4

Slightly mobile

K_foc

3098.8

¹/_n

0.879

Notes and range

EU (2022) K_f range 40.7-197.7 mL g⁻¹, K_foc range 1550.4-5202.7 mL g⁻¹, ¹/_n range 0.813-0.946, Soils =4

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.27

Calculated

Low leachability

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

Value

3.05 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

433

Threshold for concern

CT₅₀ (days)

0.54

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

1-(2-((2-(4-chlorophenyl)-2,5-dihydro-5-oxo-1H-pyrazol-1-yl)methyl)-3-methylphenyl)-1,4-dihydro-4-methyl- 5H-tetrazol-5-one (Ref: ISS7)

Minor fraction

Major fraction via pyrolysis

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹)

1-(2-((2-(4-chlorophenyl)-2,5-dihydro-5-oxo-1H-pyrazol-1-yl)methyl)-3-methylphenyl)-1,4-dihydro-4-methyl- 5H-tetrazol-5-one (Ref: ISS7)

Relevant

0.036

0.0072

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

1-[2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-(hydroxymethyl) phenyl]-1,4-dihydro-4-methyl-5H- tetrazol-5-one

3-CH2OH-S-2367

Rat, Animal

2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-(4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)benzoic acid

3-COOH-S-2367

Rat, Animal

1-[2-(methoxymethyl)-3-methylphenyl]-1,4-dihydro-4-methyl-5H-tetrazol-5-one

OHTM

Surface water, Plant, Animal

1-(4-chlorophenyl)pyrazol-3-ol

CPOH

Animal, Plant

1-methyl-4-{3-methyl-2-[(1H-pyrazole-3-yloxy)methyl]phenyl-1,4-dihydro-5H-tetrazol-5-one

de-ClPh-S-2367

Surface water (Photolysis)

1-{2-[5-hydroxy-2-(3-hydroxy-1H-pyrazol-1yl)benzyl]-3-methylphenyl}-1,4-dihydro-4-methyl-5H-tetrazol-5-one

S-2367-R1

Surface water

1-(2-{[3-hydroxy-1-(4-hydroxyphenyl)-1H-pyrazol-4-yl]methyl}-3-methylphenyl)-1,4-dihydro-4-methyl-5H-tetrazol-5-one

S-2367-R2

Surface water

1-(2-{[2-(4-hydroxyphenyl)-2,5-dihydro-5-oxo-1H-pyrazol-1-yl]methyl}-3-methylphenyl)-1,4-dihydro-4-methyl- 5H-tetrazol-5-one

S-2367-R6

Surface water

1-[2-{[1-(4-chlorophenyl)-1H-1-[2-{[1-(4-chlorophenyl)-1Hpyrazol-(hydroxymethyl)phenyl]-1,4-dihydro-5H-tetrazol-5-one

N-des-Me-S-2367

1-[2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-(hydroxymethyl)phenyl]-1,4-dihydro-5H-tetrazol-5-one

N-des-Me-3-CH2OH-S-2367

1-(2-((2-(4-chlorophenyl)-2,5-dihydro-5-oxo-1H-pyrazol-1-yl)methyl)-3-methylphenyl)-1,4-dihydro-4-methyl- 5H-tetrazol-5-one

ISS7

Surface water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

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)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

83.6

Anas platyrhynchos<.i>

Moderate

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

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

> 50.0

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose 3.2 mg kg⁻¹ soil 28 days

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

> 50

Folsomia candida

Non-target plants

> 180

Brassica napus Glycine max Beta vulgaris Allium cepa) plus others
Vegetative vigour
as g ha⁻¹

> 180

Brassica napus Glycine max Beta vulgaris Allium cepa) plus others
Emergence
as g ha⁻¹

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 109.3

Apis mellifera

Low

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

Chronic LD₅₀ µg bee⁻¹ per day

> 70.8

Apis mellifera

Bumblebees (Bombus spp.)

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

> 108.3

Bombus spp.

Low

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

> 100

Bombus spp.

Low

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

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) A5 Chrysoperla carnea

533

Beneficial insects (Parasitic wasps) A5 Aphidius rhopalosiphi

33.1

Beneficial insects (Predatory mites) A5 Typhlodromus pyri

165.9

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.048

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.015

Pimephales promelas 28 day

Moderate

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

0.34

Daphnia magna

Moderate

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

0.11

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)

0.37

Chironomus dilutus 60 day

Moderate

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

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

> 0.32

Pseudokirchneriella subcapitata

Moderate

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

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.52

Rat (nose only) 4 hr

Other Mammal toxicity endpoints

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

0.25

Mouse SF=300

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

None allocated

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

None allocated

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

0.013

Rabbit SF=100

Dermal penetration studies (%)

3-10

concentration dependant

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk for bystanders and residents if used in open fields; Negligible risk for indoor applications

Occupational

PPE/PPC recommended

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

General human health issues

Possible liver, kidney, thymus, heart and lung toxicant

Handling issues

Property

Value and interpretation

General

Not highly flammable; Not expected to autoignite
Not exposive or oxidising

CLP classification 2013

Health: H351
Environment: H400, H410

WHO Classification

High (Class III)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

metyltetraprole

French

métyltétraprole

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	24/01/2023
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