Isocycloseram (Ref: SYN547407)

Isocycloseram (Ref: SYN547407)	Last updated: 01/08/2024
(Also known as: Isocycloceram)

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: Very persistent Warning: Significant data are missing	Ecotoxicity High alert: Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High; Bees acute unknown ecotoxicity: High	Human health Low alert Warning: Significant data are missing

GENERAL INFORMATION

Description

A broad‐spectrum arylisoxazoline insecticide that is active against a wide range of insect pests.

Example pests controlled

Stinkbugs, Thrips, Caterpillars, Beetles, Flies, Mites, Diamondback moth; Cabbage white butterfly

Example applications

Corn; Coffee; Cotton; Rice; Fruit including apples and pears; Brassicas

Efficacy & activity

Availability status

Novel

Introduction & key dates

2018, first announced; 2021, first approvals

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

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

Canada, Argentina, Australia

Chemical structure

Isomerism

Isomeric substance with four active isomers. Technical substance is an isomeric mixture.

Chemical formula

C₂₃H₁₉Cl₂F₄N₃O₄

Canonical SMILES

CCN1C(=O)C(CO1)NC(=O)C2=C(C=C(C=C2)C3=NOC(C3)(C4=CC(=C(C(=C4)Cl)F)Cl)C(F)(F)F)C

Isomeric SMILES

CCN1C(=O)[C@@H](CO1)NC(=O)C2=C(C=C(C=C2)C3=NO[C@](C3)(C4=CC(=C(C(=C4)Cl)F)Cl)C(F)(F)F)C

International Chemical Identifier key (InChIKey)

WLSQDEYDCAGPIR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C23H19Cl2F4N3O4/c1-3-32-21(34)18(10-35-32)30-20(33)14-5-4-12(6-11(14)2)17-9-22(36-31-17,23(27,28)29)13-7-15(24)19(26)16(25)8-13/h4-8,18H,3,9-10H2,1-2H3,(H,30,33)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
Isocycloseram	-
Isocycloseram	-

General status

Pesticide type

Insecticide, Miticide

Substance groups

Isoxazoline insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

A GABA‐gated chloride channel allosteric modulator and acts as a non‐competitive GABA‐gated chloride channel antagonist

CAS RN

2061933-85-3

EC number

No data found

CIPAC number

None allocated

US EPA chemical code

PubChem CID

130358867

CLP index number

No data found

Molecular mass

548.3

PIN (Preferred Identification Name)

4-[(5E)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-N-[(4E)-2-ethyl-3-oxo-1,2-oxazolidin-4-yl]-2-methylbenzamide, containing 80–100% of the (5S,4R)-isomer

IUPAC name

4-[(5RS)-5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazol-3-yl]-N-[(4RS)-2-ethyl-3-oxoisoxazolidin-4-yl]-o-toluamide, containing 80–100% of the (5S,4R)-isomer

CAS name

4-[5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-ethyl-3-oxo-4-isoxazolidinyl)-2-methylbenzamide

Other status information

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)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

None identified

Physical state

Off-white coloured powder with characteristic sweet odour

Formulations

Property

Value

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

Syngenta

Example products using this active

Plinazolin

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.2

Low

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

400000

Dichloromethane

270000

Acetone

190000

Ethyl acetate

39000

Hexane

Melting point (°C)

138.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

178

Flashpoint (°C)

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

1.00 X 10⁰⁵

Calculated

Log P

5.0

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.5

Dissociation constant pKa) at 25 °C

Does not dissociate

Vapour pressure at 20 °C (mPa)

6.2 X 10^-03

Low volatility

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

2.83 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral soln: 265nm=25004, 290nm=6392
Acidic soln: 265nm=22632, 290nm=4906
Basic soln: 265nm=22363, 290 nm=5084

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)

390

Very persistent

DT₅₀ (lab at 20 °C)

390

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Australian 2022 public dosier: Lab studies DT₅₀ range 56-723 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.7

Note

Published literature Rl50 range 2.2-3.3 days, 2 field crops, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Stable

Note

Stable at pH 4-7, hydrolyses quickly at pH 9

Water-sediment DT₅₀ (days)

Water 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)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

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

6.2

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)

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

Ref: SYN549543

Ref: SYN549544

Ref: SYN549543

Ref: SYN549107

Major fraction

0.260

Ref: SYN550738

Major fraction

0.110

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Ref: SYN549431

Plant

Ref: SYN548569

Animal

Ref: SYN549431

Animal

Ref: SYN549436

Animal

Ref: SYN549544

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

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)

> 2000

Unknown species

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

> 500

Eisenia foetida corr

Moderate

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

Soil micro-organisms

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)

0.26

Apis mellifera

High

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

0.28

Apis mellifera

High

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

0.08

Apis mellifera bee larvae

High

Chronic

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)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites) -

0.0059

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)

0.13

Oncorhynchus mykiss

Moderate

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

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

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

0.017

Daphnia magna

High

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

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)

0.000015

Chironomus riparius

High

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)

1.2

Lemna gibba

Moderate

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

0.27

Skeletonema costatum

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)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.02

Australia

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

0.08

Australia

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

[Appropriate PPE/PPC is recomended]

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

Dermal penetration studies (%)

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

Mainly excreted via bile and faeces, and to lesser extent, via 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

No information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not highly flammable

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Stable for around 12 months at 20 DegC. Less stable at higher temperatures

TRANSLATIONS

Language

Name

English

Isocycloseram

French

isocycloséram

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	01/08/2024
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