Isoflucypram

Isoflucypram	Last updated: 05/01/2021
(Not known by any other names)

SUMMARY

A new cereals fungicide which is not yet approved for use within the EU. Isoflucypram las a low aqueous solubility and is not considered highly volatile. Under certain conditions the sunstance may be persistent in both soil and water systems. No major human health issues have been identified but it may be a skin sensitiser or cause skin irritation. It is toxic to aquatic systems but is not considered harmful to insect pollinators.

GENERAL INFORMATION

Description

A new fungicide for the control of various fungal pathogens on cereals

Example pests controlled

Mycosphaerella graminicola, Puccinia recondita, Puccinia striiformis, Pyrenophora tritici-repentis

Example applications

Cereals including wheat, rye, triticale,barley, oats

Efficacy & activity

Availability status

Novel

Introduction & key dates

First UK registration application 2019

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

UK/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

Also used in

Chemical structure

Isomerism

Does not demonstrates stereo-isomerism.

Chemical formula

C₁₉H₂₁ClF₃N₃O

Canonical SMILES

FC(F)c1nn(C)c(F)c1C(=O)N(Cc1cc(Cl)ccc1C(C)C)C1CC1

Isomeric SMILES

Not applicable

International Chemical Identifier key (InChIKey)

JEFUQUGZXLEHLD-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H21ClF3N3O/c1-10(2)14-7-4-12(20)8-11(14)9-26(13-5-6-13)19(27)15-16(17(21)22)24-25(3)18(15)23/h4,7-8,10,13,17H,5-6,9H2,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Pyrazolecarboxamide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

Substance origin

Synthetic

Mode of action

Succinate dehydrogenase inhibitor

CAS RN

1255734-28-1

EC number

Not allocated

CIPAC number

Not allocated

US EPA chemical code

PubChem CID

Molecular mass

399.84

PIN (Preferred Identification Name)

N-((5-chloro-2-(propan-2-yl)phenyl)methyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

IUPAC name

N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

CAS name

N-((5-chloro-2-(1-methylethyl)phenyl)methyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

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

Whoite powder

Formulations

Property

Value

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

Isoflucypram EC50
Vimoy Iblon

Example products using this active

Bayer Crop Science

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)

1.8

Low

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

1200

Heptane

260000

Toluene

97000

Methane

260000

Acetone

Melting point (°C)

108.8

Boiling point (°C)

215

Degradation point (°C)

Flashpoint (°C)

Not expected to self-ignite; Not highly flammable

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

1.00 X 10⁰⁴

Calculated

Log P

4.0

at 25°C

High

Bulk density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

No dissociation

Vapour pressure at 20 °C (mPa)

1.2 X 10^-04

Low volatility

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

2.7 X 10^-05

Non-volatile

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

Neutral: 201nm=34777, 217nm=22116
Acid: 201nm=37165, 217nm=22539
Basic: 222bnm=21432

Surface tension (mN m⁻¹)

68.2

at 20 °C 83%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

318.5

Persistent

DT₅₀ (lab at 20 °C)

318.5

Persistent

DT₅₀ (field)

45.1

Moderately persistent

DT₉₀ (lab at 20 °C)

1143

Very persistent

DT₉₀ (field)

324

DT₅₀ modelling endpoint

Note

EU 2019 dossier lab studies DT₅₀ (normalised) range 206-665 days; DT₉₀ (normalised) range 685-2206 days, Soils=7; Field studies DT₅₀ (normalised) range 9.84-94.7 days; DT₉₀ (measured) range 69.6-3090 days, Soils=6

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

Stable

Note

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

Value

Stable

Note

Stable at all relevant pH values

Water-sediment DT₅₀ (days)

1000

Stable

Water phase only DT₅₀ (days)

1000

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

28.45

Slightly mobile

K_foc

1346

¹/_n

0.907

Notes and range

EU 2019 dossier K_f range 11,.26-58.71 mL g⁻¹, K_foc range 1151-1569 mL g⁻¹, ¹/_n range 0.869-0.999, Soils=5

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.44

Calculated

Low leachability

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

Value

3.63 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

2-(4-chloro-2-((cyclopropyl((3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazol-4-yl)-carbonyl)amino)-methyl)phenyl}-propanoic acid (Ref: BCS-CY26497)

Soil

0.096

Minor Fraction; Relevant

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

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)

3776

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.068

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.201

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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)

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

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

> 2.48

Lemna gibba as NOEC

Moderate

Non-target plants

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

> 2.02

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)

> 100.0

Apis mellifera

Low

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

106.3

Apis mellifera

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)

> 100

Bombus terrestris

Low

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

> 200.2

Bombus terrestris

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

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

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

28.0

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

30.6

Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

14.13

Aphidius rhopalosiphi

% Effect

Soil micro-organisms

Nitrogen transformation: No significant adverse effect

Dose: 0.53 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

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.5

Rat 4hr (aerosol nose only)

Other Mammal toxicity endpoints

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

0.04

Dog SF=100

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

0.7

rabbit SF=100

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

Not allocated

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

0.04

Dog SF=100

Dermal penetration studies (%)

2-5

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk for prescribed uses

Occupational

Low risk for prescribed uses

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

Eye irritant

Phototoxicant

General human health issues

Possible liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317, H332
Environment: H400, H410

EC Risk Classification

EC Safety Classification

WHO Classification

UN Number

Waste disposal & packaging

TRANSLATIONS

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Name

English

isoflucypram

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Record last updated:	05/01/2021
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