Isopyrazam (Ref: SYN 520453)

Isopyrazam (Ref: SYN 520453)	Last updated: 12/01/2021
(Also known as: A15149W)

GENERAL INFORMATION

Description

A novel 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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2026

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/03/2023

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
		✓	✓		✓		✓	✓

Also used in

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

General status

Pesticide type

Fungicide

Substance group

Pyrazole

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

CIPAC number

US EPA chemical code

129222

PubChem CID

25271089

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

None identified

Physical state

Off-white coloured solid

Related substances & organisms

epoxiconazole

cyprodinil

Formulations

Property

Value

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

Bontima
Seguris Flexi
Zulu
Reflect 125 EC

Example products using this active

Syngenta Crop Protection

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

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

30.3

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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)

Soil

0.236

Major fraction, Relevant

3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (Ref: CSCD465008)

Soil

0.115

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

CSAA798670

Soil

0.054

dihydroxy isopyrazam

CDCD656800

Hens; Animal (Milk, Tissue)

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide

CSCC210616

Soil

0.080

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

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⁻¹ Feed

Colinus virginianus

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

32.5

Colinius virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0258

Cyprinus carpio

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00287

Pimephales promelas 28 day

High

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

0.044

Daphnia magna

High

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

0.013

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)

1.0

Chironomus riparius

Moderate

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

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

> 0.5

Lemna gibba

Moderate

Non-target plants

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

2.2

Pseudokirchneriella subcapitata

Moderate

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)

> 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)

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)

Eisenia foetida 56 days

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

174.75

Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

41.2

Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 1.67 mg kg⁻¹ soil 28 days

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

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)

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

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

; ; ; ;

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
USEPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code 9

CLP classification 2013

Health: H317, H361
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22, R43
N - Dangerous for the environment: R50/53

EC Safety Classification

S36/37, S60

WHO Classification

NL (Not listed)

UN Number

3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

isopyrazam

French

isopyrazam

German

Isopyrazam

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

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