Methoxyfenozide (Ref: RH 2485)

Methoxyfenozide (Ref: RH 2485)	Last updated: 22/08/2024
(Also known as: RH 112485)

SUMMARY

Methoxyfenozide is a broad-spectrum insecticide. It has a low aqueous solubility and a low volatility. Based on its chemical properties there is a high risk of leaching to groundwater and under some conditions it may be persistent in soil systems. It has a low oral toxicity to mammals and no significant risk issues to human health have been identified. It has a low toxicity to birds and honeybees but is relatively more toxic to aquatic species and earthworms.

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: GUS: High leachability	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Endocrine disrupter

GENERAL INFORMATION

Description

An insecticide used to control various insects including moths and butterflies

Example pests controlled

Codling moth; Lesser appleworm; Oriental fruit moth; Leafrollers; Loopers; Cotton bollworm; Armyworm; Bud moths

Example applications

Leafy vegetables; Fresh herbs; Lettuce; Salads; Herbs; Brassicas; Cotton; Pome fruit; Grapes; Sweetcorn; Maize; Peppers; Aubergines

Efficacy & activity

The effectiveness of methoxyfenozide for the approved uses has been deminstrated via field trials and extensive use.

Availability status

Current

Introduction & key dates

1996, first reported; 1998, first marketed

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2026

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Slovakia

Date EC 1107/2009 inclusion expires

31/03/2026

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
	✓	✓		✓	✓

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

Australia, USA, Argentina, Brazil, Colombia, Israel, Japan, Mexico, Korea, Egypt, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₂₂H₂₈N₂O₃

Canonical SMILES

CC1=CC(=CC(=C1)C(=O)N(C(C)(C)C)NC(=O)C2=C(C(=CC=C2)OC)C)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

QCAWEPFNJXQPAN-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H28N2O3/c1-14-11-15(2)13-17(12-14)21(26)24(22(4,5)6)23-20(25)18-9-8-10-19(27-7)16(18)3/h8-13H,1-7H3,(H,23,25)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Carbohydrazide compound; Monomethoxybenzene compound

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - butylhydrazine

Substance origin

Synthetic

Mode of action

A moulting accelerator that is an agonist of the hormone 20-hydroxyecdysone. Ecdysone receptor agonist.

CAS RN

161050-58-4

EC number

605-245-2

CIPAC number

656

US EPA chemical code

121027

PubChem CID

105010

CLP index number

No data found

Molecular mass

368.47

PIN (Preferred Identification Name)

IUPAC name

N-tert-butyl-N'-(3-methoxy-o-toluoyl)-3,5-xylohydrazide

CAS name

3-methoxy-2-methylbenzoic acid 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazide

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

Cydia pomonella, Deraeocoris brevis, Spodoptera exigua

Physical state

White powder

Formulations

Property

Value

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

Bayer CropScience
Dow AgroSciences
Agrovista

Example products using this active

Intrepid
Runner
Prodigy
Falcon
Runner
Trotter

Formulation and application details

Often supplied as a soluble concentrate that is mixed with water 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)

3.3

Low

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

115000

Methanol

69000

Acetone

28000

Dichloromethane

600

Xylene

Melting point (°C)

185

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

262.9

Flashpoint (°C)

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

5.25 X 10⁰³

Calculated

Log P

3.72

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

0.634

Dissociation constant pKa) at 25 °C

12.20

Vapour pressure at 20 °C (mPa)

1.33 X 10^-02

Low volatility

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

1.64 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

Negligible

24 hr

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

pH 7: 216nm=12819, 280nm=2503, 290nm=1561
pH 2: 216nm=12881, 279nm=2916, 290nm=1912
pH 10: 225nm=11312, 276nm=2937, 290nm=1548

Surface tension (mN m⁻¹)

58.0

at 20 °C 99.4%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

456

Very persistent

DT₅₀ (lab at 20 °C)

456

Very persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

1905

Very persistent

DT₉₀ (field)

717

DT₅₀ modelling endpoint

Note

EU 2016 dossier lab studies range DT₅₀ 81->1000 days, DT₉₀ range 290-6340 days, Soils=14; EU 2004 dossier lab studies range 336-1100 days, DT₉₀ range 1618 – 5302 days, field study range 39-133 days, DT₉₀ range 434->1000 days; Other sources: 683 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.3

Note

Published literature RL₅₀ range 4.3-6.2 days, 2 field & undercover grown crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9, 25 °C

Water-sediment DT₅₀ (days)

208.6

Slow

Water phase only DT₅₀ (days)

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)

Moderately mobile

K_oc (mL g⁻¹)

402

Notes and range

EU 2004 dossier K_oc range 200-922 mL g⁻¹; Other sources: 365 mL g⁻¹ (DW3)

Freundlich

K_f (mL g⁻¹)

2.87

Moderately mobile

K_foc (mL g⁻¹)

231

¹/_n

0.936

Notes and range

EU 2016 dossier K_f range 1.53-6.2 mL g⁻¹, kfoc range 132-365 mL g⁻¹, ¹/_n range 0.85-1.00, Soils=16

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.00

Calculated

High leachability

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

Value

3.13 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

3.3

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)

Whole fish

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

(N-(3-methoxy-2-methylbenzoyl)-N-(3-carboxy-5-methylbenzoyl)-N-tert-butylhydrazine) (Ref: RH 131154)

Major fraction

0.158

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)

(N-(3-methoxy-2-methylbenzoyl)-N-(3-carboxy-5-methylbenzoyl)-N-tert-butylhydrazine) (Ref: RH 131154)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

desmethylated methoxyfenozide; methoxyfenozide metabolite M14

Animal (Urine, Faeces); Rat; Water/sediment

hydroxy methyl methoxyfenozide; methoxyfenozide metabolite M24

Animal (Urine, Faeces)

3,5-dimethylbenzoic acid N-tert-butyl-N‘-(3-hydroxy-2-methylbenzoyl)-hydrazide

RH-117236

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)

> 10

Rat 2 yr

High

(ppm diet)

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

1552

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

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)

82.7

Colinus virginianus NOEL

Moderate

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

> 607

Eisenia foetida

Moderate

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

2.04

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 1.96 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

0.64

Folsomia candida

Non-target plants

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)

> 2000

Apis mellifera

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)

Harmless

Chrysoperla carnea

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

> 192.0

Aphidius rhopalosiphi

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

> 192

Typhlodromus pyri

Beneficial insects (Ground beetles) as Mortality LR₅₀ g ha⁻¹

> 960

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

> 4.2

Oncorhynchus mykiss

Moderate

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

2.4

Pimephales promelas 33 day

Moderate

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

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

3.7

Daphnia magna

Moderate

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

0.39

Daphnia magna

Moderate

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

1.2

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.257

Chironomus riparius 48 hr

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.0065

Chironomus riparius

High

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

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

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

> 3.4

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.3

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.1

Rat SF=100

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

0.1

Dog SF=100

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

0.06

Dog SF=100

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

0.06

Dog SF=100

Dermal penetration studies (%)

0.5-8

concentration dependent

Dangerous Substances Directive 76/464

[Acceptable for proposed uses, PPE/PPC advised]

Exposure Routes

Public

Low for propsoed uses

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 the faeces and biliary activity.

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

No data found

General human health issues

Potential endocrine effects on thyroid and adrenal glands at high doses
Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H400, H410, H411

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

methoxyfenozide

French

methoxyfenozide

German

Methoxyfenozid

Danish

methoxyfenozid

Italian

metossifenozide

Spanish

metoxifenocida

Greek

Polish

metoksyfenozyd

Swedish

Hungarian

metoxifenozid

Dutch

Norwegian

Record last updated:	22/08/2024
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