Methoxyfenozide (Ref: RH 2485)

Methoxyfenozide (Ref: RH 2485)	Last updated: 19/02/2021
(Also known as: RH 112485)

SUMMARY

An insectide approved for use in the EU and many other countries on a broad range of fruit and vegetables. 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.

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2026

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

UK/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
	✓	✓	✓	✓	✓		✓	✓

Also used in

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

Chemical structure

Isomerism

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

No data

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 group

Diacylhydrazine

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

CAS RN

161050-58-4

EC number

CIPAC number

656

US EPA chemical code

121027

PubChem CID

105010

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

18A

Fungicide Resistance Classification (FRAC)

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

Intrepid
Runner
Prodigy
Falcon
Runner
Trotter

Example products using this active

Bayer CropScience
Dow AgroSciences
Agrovista

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)

Not expected to self ignite; Not highly flammable

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

5.25 X 10⁰³

Calculated

Log P

3.72

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

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

2.87

Moderately mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.158

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

desmethylated methoxyfenozide; methoxyfenozide metabolite M14

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

hydroxy methyl methoxyfenozide; methoxyfenozide metabolite M24

Animal (Urinary, Faeces)

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

RH-117236

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 10

Rat 2 year

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 4.2

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

2.4

Pimephales promelas 33 day

Moderate

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

3.7

Daphnia magna

Moderate

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

0.39

Daphnia magna

Moderate

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 48hr

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)

Non-target plants

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

> 3.4

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

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)

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)

> 607

Eisenia foetida

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Harmless

Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Harmless

Chrysoperla carnea

Soil micro-organisms

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

Dose: 1.96 kg ha⁻¹ 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)

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

Notes

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

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

CLP classification 2013

Environment: H400, H410, H411

EC Risk Classification

N - Dangerous for the environment: R51/53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

methoxyfenozide

French

methoxyfenozide

German

Methoxyfenozid

Danish

methoxyfenozid

Italian

metossifenozide

Spanish

metoxifenocida

Greek

Polish

metoksyfenozyd

Swedish

Hungarian

metoxifenozid

Dutch

Record last updated:	19/02/2021
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