Tebufenozide (Ref: RH 5992 2F )

Tebufenozide (Ref: RH 5992 2F )	Last updated: 21/08/2024
(Also known as: tebufenoxide; tebufonozide)

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 Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate	Human health Low alert

GENERAL INFORMATION

Description

An insecticide used to control Lepidopterous larvae in a wide variety of cropping situations

Example pests controlled

Grape berry moth; Codling moth; European grapevine moth; Grape leafroller; Vine moth; Apple brown tortrix moth;

Example applications

Fruit including grapes, apples, pears, berries; Brassicas, leafy vegetables, turnips, and fruiting vegetables

Efficacy & activity

Availability status

Current

Introduction & key dates

1994, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2029

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Germany

Date EC 1107/2009 inclusion expires

31/01/2027

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

Morocco

Chemical structure

Isomerism

None

Chemical formula

C₂₂H₂₈N₂O₂

Canonical SMILES

CCC1=CC=C(C=C1)C(=O)NN(C(=O)C2=CC(=CC(=C2)C)C)C(C)(C)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

QYPNKSZPJQQLRK-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H28N2O2/c1-7-17-8-10-18(11-9-17)20(25)23-24(22(4,5)6)21(26)19-13-15(2)12-16(3)14-19/h8-14H,7H2,1-6H3,(H,23,25)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Carbohydrazide compound

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier: t-butyl hydrazine <0.001 g kg⁻¹

Substance origin

Synthetic

Mode of action

Accelerates molting, mainly stomach action. Ecdysone receptor agonist.

CAS RN

112410-23-8

EC number

412-850-3

CIPAC number

724

US EPA chemical code

129026

PubChem CID

91773

CLP index number

616-076-00-9

Molecular mass

352.47

PIN (Preferred Identification Name)

N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide

IUPAC name

N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide

CAS name

3,5-dimethylbenzoic acid 1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)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, Planotortrix octo, Plutella xylostella, Spodoptera exigua, Spodoptera littoralis

Physical state

Off-white powder

Formulations

Property

Value

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

Dow AgroSciences
Hokko Chemical Co.
Nippon soda

Example products using this active

Mimic
Confirm
Romdan

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.83

Low

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

23800

Ethyl acetate

74800

Acetone

130000

Methanol

3200

Toluene

Melting point (°C)

191

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

start temp.

Flashpoint (°C)

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

1.78 X 10⁰⁴

Calculated

Log P

4.25

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.03

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.56 X 10^-04

Low volatility

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

6.59 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Methanol: 235nm = 16331
Acidic methanol: 233nm = 16458
Basic methanol: 235nm = 15844

Surface tension (mN m⁻¹)

71.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

400

Very persistent

DT₅₀ (lab at 20 °C)

26.2

Non-persistent

DT₅₀ (field)

24.2

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 20.8-31.2 days, field studies DT₅₀ range 10.2-81.7 days; Other sources: 348 days (DW4), 105-704 (Q3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

37.7

Note

Published literature RL₅₀ range 3.0-69.5 days, 3 field grown crops, various matrices, n=6

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

38.5

Note

Published literature RL₅₀ range 3.5-58.7 days, 3 field grown crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

145.4

Slow

Water phase only DT₅₀ (days)

12.6

Moderately fast

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)

5.73

Slightly mobile

K_foc (mL g⁻¹)

572

¹/_n

1.005

Notes and range

EU dossier kf range 1.616-8.208 mL g⁻¹, kfoc range 351-894 mL g⁻¹, ¹/_n range 0.943-1.138, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.72

Calculated

Low leachability

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

Value

4.78 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

11.89

Calculated using the Atkinson method. Assumed 0.5E+06 OH/cm³, 24 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-(N'-(3,5-dimethylbenzoyl_-N-(1,1-dimethylethyl)hydrazinocarbonyl)benzoic acid (Ref: RH-2651)

Major fraction

0.200

4-(N'-(3,5-dimethylbenzoyl-N-(1,1-dimethylethyl)hydrazinocarbonyl)phenyl acetic acid (Ref: RH-2703)

Minor fraction

0.08

N-(1,1-dimethyethyl)-N-(4-acetylebenzoyl)-3,5-dimethylbenzohydrazine (Ref: RH-6595)

Minor fraction

0.088

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)

4-(N'-(3,5-dimethylbenzoyl_-N-(1,1-dimethylethyl)hydrazinocarbonyl)benzoic acid (Ref: RH-2651)

Relevancy unknown

N-(1,1-dimethyethyl)-N-(4-acetylebenzoyl)-3,5-dimethylbenzohydrazine (Ref: RH-6595)

Relevancy unknown

Other known metabolites

None

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)

5.5

Rat 2 yr

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Colinus virginianus

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)

> 1000

Eisenia foetida

Low

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

> 1000

Eisenia foetida

Low

Soil micro-organisms

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

Dose: Unknown 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 2400

Unknown species
Vegetative vigour, NOEL
as g ha⁻¹

> 2400

Unknown species
Seedling emergence, NOEL
as g ha⁻¹

Honeybees (Apis spp.)

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

> 234

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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

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) as Mortality LR₅₀ g ha⁻¹

> 576

Coccinella septempunctata

Beneficial insects (Lacewings) as Mortality LR₅₀ g ha⁻¹

> 576

Chrysoperla carnea

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

> 432.0

Aphidius rhopalosiphi Adult

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

165.4

Typhlodromus pyri Protonymph

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

> 432

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

3.0

Lepomis macrochirus

Moderate

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

0.71

Pimephales promelas

Moderate

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

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

3.8

Daphnia magna

Moderate

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

0.029

Daphnia magna

Moderate

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

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

0.82

Americamysis bahia

Moderate

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)

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

0.23

Scenedesmus subspicatus

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.3

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.02

Dog SF=100

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

None allocated

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

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

0.008

Dog SF=100

Dermal penetration studies (%)

0.2-2.1

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Possible risk to operators particularly in orchards - PPE/PPC advised
Acceptable risk to other farm workers

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

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

Liver and kidney toxicant
Known to be It is hemotoxic causing red blood cell damage

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: 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

tebufenozide

French

tebufenozide

German

Tebufenozid

Danish

tebufenozid

Italian

tebufenozide

Spanish

tebufenozid; tebufenocida

Greek

Polish

tebufenozyd

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	21/08/2024
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