Tebufenozide (Ref: RH 5992 2F )

Tebufenozide (Ref: RH 5992 2F )	Last updated: 15/03/2021
(Also known as: tebufenoxide; tebufonozide)

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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

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

31/05/2021

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

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

No data

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 group

Diacylhydrazine

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

CAS RN

112410-23-8

EC number

412-850-3

CIPAC number

724

US EPA chemical code

129026

PubChem CID

91773

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

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

Mimic
Confirm
Romdan

Example products using this active

Dow AgroSciences
Hokko Chemical Co.

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

Bulk 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

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 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 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

5.73

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.200

Major fraction, Relevancy unknown

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

Soil

0.08

Minor fraction, Relevancy unknown

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

Soil

0.088

Minor fraction, Relevancy unknown

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

5.5

Rat 2 year

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

3.0

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.71

Pimephales promelas

Moderate

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

3.8

Daphnia magna

Moderate

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

0.029

Daphnia magna

Moderate

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)

Non-target plants

> 2400

Unknown species
Vegetative vigour, NOEL
as g ha⁻¹

> 2400

Unknown species
Seedling emergence, NOEL
as g ha⁻¹

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

0.23

Scenedemus subspicatus

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)

> 234

Low

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

> 100

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)

> 1000

Eisenia foetida

Low

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

> 1000

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

432.0

>
Aphidius rhopalosiphi adults

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

165.4

Typhlodromus pyri protonymph

% Effect

Soil micro-organisms

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

Dose: Unknown 28days

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)

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

EC Risk Classification

N - Dangerous for the environment: R51, R53

EC Safety Classification

S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

tebufenozide

French

tebufenozide

German

Tebufenozid

Danish

tebufenozid

Italian

tebufenozide

Spanish

tebufenozid; tebufenocida

Greek

Polish

tebufenozyd

Swedish

Hungarian

Dutch

Record last updated:	15/03/2021
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