Isopyrazam (Ref: SYN 520453)

Isopyrazam (Ref: SYN 520453)	Last updated: 18/07/2024
(Also known as: A15149W)

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: Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Possible Carcinogen; Reproduction/development effects

GENERAL INFORMATION

Description

A persisent and broad spectrum fungicide for the cereals and some other crops

Example pests controlled

Septoria tritici, Rusts, Black sigatoka (banana leaf spot disease); Scab; Powder mildews; Alternaria

Example applications

Cereals including winter & spring barley, wheat; Bananas; vegetables, Ornamentals; Various speciality crops

Efficacy & activity

Barley/Rhynchosporium=Moderate; Barley/Mildew=Low; Barley/Rust=Moderate; Barley/Net blotch=Moderate; Barley/Ramularia=Moderate

Availability status

Current

Introduction & key dates

2008, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2026

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Norway/Greece

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

Morocco

Chemical structure

Isomerism

A chiral molecule. The technical material is an isomeric mixture of the syn-isomer (approx. 70-100%) and the anti-isomer (approx. 0-30%)

Chemical formula

C₂₀H₂₃F₂N₃O

Canonical SMILES

CC(C)C1C2CCC1C3=C2C=CC=C3NC(=O)C4=CN(N=C4C(F)F)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

XTDZGXBTXBEZDN-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H23F2N3O/c1-10(2)16-12-7-8-13(16)17-11(12)5-4-6-15(17)23-20(26)14-9-25(3)24-18(14)19(21)22/h4-6,9-10,12-13,16,19H,7-8H2,1-3H3,(H,23,26)/f/h23H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
isopyrazam	Unstated isomer
isopyrazam monohydrate	Variant

General status

Pesticide type

Fungicide

Substance groups

Pyrazole fungicide; Carboximide fungicide; Pyrazolecarboximide fungicide

Minimum active substance purity

>920 g kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

Protectant, foliar absorption, translocates, inhibits respiration and spore germination and so germ tude elongation - a succinate dehydrogenase inhibitor

CAS RN

881685-58-1

EC number

632-619-2

CIPAC number

963

US EPA chemical code

129222

PubChem CID

25271089

CLP index number

No data found

Molecular mass

359.4

PIN (Preferred Identification Name)

mixture of 2 syn-isomers rac-3-(difluoromethyl)-1-methyl-N-[(1R,4S,9R)-9-(propan-2-yl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-pyrazole-4-carboxamide and 2 anti-isomers rac-3-(difluoromethyl)-1-methyl-N-[(1R,4S,9S)-9-(propan-2-yl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-pyrazole-4-carboxamide

IUPAC name

mixture of 2 isomers 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide and 2 aisomers 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide

CAS name

3-(difluoromethyl)-1-methyl-N-[1,2,3,4-tetrahydro-9-(1-methylethyl)-1,4-methanonaphthalen-5-yl]-1H-pyrazole-4-carboxamide

Other status information

Marine pollutant; PAN listed Highly Hazardous Chemical

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)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

None identified

Physical state

Off-white coloured solid

Formulations

Property

Value

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

Syngenta Crop Protection

Example products using this active

Bontima
Seguris Flexi
Zulu
Reflect 125 EC

Formulation and application details

Usually supplied as an emulsifiable concentrate and used as a foliar spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.55

Low

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

314000

Acetone

303111

Dichloromethane

1170

Hexane

77100

Toluene

Melting point (°C)

137

Boiling point (°C)

267

Degradation point (°C)

261

Flashpoint (°C)

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

1.78 X 10⁰⁴

Calculated

Log P

4.25

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.3 X 10^-04

Low volatility

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

1.14 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

225nm = 169771 isomer mean
295nm = 6712.3 isomer mean

Surface tension (mN m⁻¹)

63.1

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

244

Persistent

DT₅₀ (lab at 20 °C)

244

Persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

534.4

Very persistent

DT₉₀ (field)

317.6

DT₅₀ modelling endpoint

Note

EU dossier DT₅₀ Lab studies range 29.8-976 days (normalised), DT₉₀ range 132-1000 days; Field studies DT₅₀ range 9.11-173 days (normalised), DT₉₀ range 63.5-2089 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

54.3

Stable

Note

Natural light, 30-50 DegN, 12hr day length

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

Value

Stable

Note

Stable at all environmentally pH's

Water-sediment DT₅₀ (days)

628

Stable

Water phase only DT₅₀ (days)

2.3

Moderately fast

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

30.3

Slightly mobile

K_foc (mL g⁻¹)

2416

¹/_n

0.942

Notes and range

EU dossier K_f range 11.56-51.83 mL g⁻¹, K_foc range 1732-2491 mL g⁻¹, ¹/_n range 0.92-0.97, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.15

Calculated

Low leachability

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

Value

2.49 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

2.29

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

441

No significant bioaccumulation potential

Threshold for concern

CT₅₀ (days)

No data

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (Ref: M700F002)

Major fraction

0.115

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (Ref: CSAA798670)

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Ref: CSCC210616)

3-(difluoromethyl)-1-methyl-N-((1R,4S,9R)-1,2,3,4,-tetrahydro-9-(2-hydroxypropan-2-yl)-1,4-methanonaphthalen-5-yl)pyrazsaole-4-carboxamide (Ref: CSCD459488)

Major fraction

0.236

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

3-(difluoromethyl)-1-methyl-N-((1R,4S,9R)-1,2,3,4,-tetrahydro-9-(2-hydroxypropan-2-yl)-1,4-methanonaphthalen-5-yl)pyrazsaole-4-carboxamide (Ref: CSCD459488)

Not relevant

3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (Ref: M700F002)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

dihydroxy isopyrazam

CDCD656800

Hens; Animal (Milk, Tissue)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

2000

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

> 250

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

5620 mg kg feed⁻¹

Colinus virginianus

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

32.5

Colinus virginianus

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

Eisenia foetida 56 day

Moderate

Soil micro-organisms

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

Dose: 1.67 mg kg⁻¹ soil 28 Day

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)

> 200

Low

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

> 192.3

Low

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

Chronic

Notes

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 bee species (1)

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

Mode of exposure

Other bee species (2)

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

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as Mortality LR₅₀ g ha⁻¹

405

Chrysoperla carnea

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

41.2

Aphidius rhopalosiphi

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

174.75

Typhlodromus pyri

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)

0.0258

Cyprinus carpio

High

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

0.00287

Pimephales promelas 28 day

High

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

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

0.044

Daphnia magna

High

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

0.013

Daphnia magna

Moderate

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

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)

1.0

Chironomus riparius 27 day

Moderate

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

56.0

Chironomus riparius

Moderate

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

> 0.5

Lemna gibba

Moderate

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

2.2

Pseudokirchneriella subcapitata

Moderate

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)

2000

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.28

Rat 4 hr

Other Mammal toxicity endpoints

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

0.03

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

0.2

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

Not applicable

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

0.05

Dermal penetration studies (%)

1.0

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

Rapid and extensive elimination ~4-8hr 48-58% in bile, 26-36% in faeces and 15-16% in urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant
US EPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9

CLP classification 2013

Health: H317, H361
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

isopyrazam

French

isopyrazam

German

Isopyrazam

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	18/07/2024
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