Tebufenpyrad (Ref: AC 801757)

Tebufenpyrad (Ref: AC 801757)	Last updated: 12/01/2021
(Also known as: MK 239; BAS 318l; SAN 831A)

GENERAL INFORMATION

Description

A contact and stomach action acaricide used to control mites on fruit trees and other crops

Example pests controlled

All stages of Tetranychus, Panonychus, Oligonychus and Eotetranychus spp. including European red mite, Fruit tree red spider mite and the Two spotted spider mite; Aphids

Example applications

Apples; Pears; Strawberries; Commercial greenhouses; Ornamentals including roses; Hops

Efficacy & activity

Availability status

Current

Introduction & key dates

1993, Japan; 2002, USA

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/10/2025

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Belgium

Date EC 1107/2009 inclusion expires

31/10/2022

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

Chemical structure

Isomerism

Chemical formula

C₁₈H₂₄ClN₃O

Canonical SMILES

CCC1=NN(C(=C1Cl)C(=O)NCC2=CC=C(C=C2)C(C)(C)C)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ZZYSLNWGKKDOML-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H24ClN3O/c1-6-14-15(19)16(22(5)21-14)17(23)20-11-12-7-9-13(10-8-12)18(2,3)4/h7-10H,6,11H2,1-5H3,(H,20,23)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
tebufenpyrad	-

General status

Pesticide type

Acaricide

Substance group

Pyrazolium

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

A mitochondrial electron transport inhibitor, non-systemic with contact and stomach action

CAS RN

119168-77-3

EC number

CIPAC number

725

US EPA chemical code

090102

PubChem CID

86354

Molecular mass

333.8

PIN (Preferred Identification Name)

N-[(4-tert-butylphenyl)methyl]-4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide

IUPAC name

N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide

CAS name

4-chloro-N-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide

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

Yetranychus kanzawai, Tetranychus urticae

Physical state

Colourless crystalline solid

Formulations

Property

Value

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

Masai

Example products using this active

BASF
Summit Agro

Formulation and application details

Often supplied as water soluble bag formulations or emulsifiable concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.39

Low

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

1044000

Dichloromethane

255000

Hexane

818000

Methanol

819000

Acetone

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

250

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

8.51 X 10⁰⁴

Calculated

Log P

4.93

High

Bulk density (g ml⁻¹)

1.17

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0016

Low volatility

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

1.10 X 10^-03

Non-volatile

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

223nm = 16882, 295nm = 82

Surface tension (mN m⁻¹)

67.4

at 20.3°C 99.6%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

33.9

Moderately persistent

DT₅₀ (field)

4.5

Non-persistent

DT₉₀ (lab at 20 °C)

191.1

Persistent

DT₉₀ (field)

26.7

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 17.7-76.5 days (normalised), DT₉₀ range 88.6-575 days; field studies DT₅₀ range 0.05-22.4 days, DT₉₀ range 3.0-74.3 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

6.8

Note

Published literature RL₅₀ range 5.3-8.3 days, 2 field grown crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Data for natural sunlight at 40 deg N. Other data: DT₅₀ 187 days natural light, 40 deg N, 28 days (A5)

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

Value

Stable

Note

Stable pH 4 to pH 9 up to 120 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

6.6

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

121

Non-mobile

K_oc

5992

Notes and range

EU dossier K_d range 18-mK_oc range 2159-11936 mL g⁻¹, Soils=9

Freundlich

K_f

88.1

Non-mobile

K_foc

4204

¹/_n

0.94

Notes and range

EU dossier K_f range 24.8-388 mL g⁻¹, K_foc range 1894-8552 mL g⁻¹, ¹/_n range 0.817-1.122, Soils=9

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.25

Calculated

Low leachability

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

Value

2.71 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

N-(4-(1-carboxy-1-methylethyl)-benzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboximide (Ref: CL-810721)

Soil

0.234

Major fraction, Relevant

4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide (Ref: CL 810729)

Soil

0.122

Major fraction, Relevant

4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxylic acid (Ref: CL 810728)

Soil

0.051

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-chloro-3-ethyl-N-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1-methyl-1H-pyrazole-5-carboxamide (Ref: CL 810720)

Animal

N-(4-t-butylbenzyl)-3-acetyl-4-chloro-1-hloro-1- (Ref: CL 810719)

Soil

4-chloro-3-(1-hydroxyethyl)-N-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1-methyl-1H-pyrazole-5-carboxamide (Ref: CL 810722)

Animal

2-[4-({[4-chloro-3-(1-hydroxyethyl)-1-methyl-1H-pyrazol-5-yl]carbonyl}amino)phenyl]-2-methylpropanoic acid (Ref: CL 810723)

Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

953

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 202

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 48.5

Rat

High

(ppm diet)

> 300

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

≥ 17

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 439 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

6.6

Anas platyrhynchos NOEL

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.023

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00245

Oncorhynchus mykiss

High

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

0.046

Daphnia magna

High

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

0.020

Daphnia magna

Moderate

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

0.022

Americamysis bahia

High

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

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

0.19

Chironomus riparius

Moderate

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

0.64

Chironomus riparius

Moderate

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

Non-target plants

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

0.052

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)

6.7

Moderate

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

60.3

Moderate

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)

20.5

Eisenia foetida corr

Moderate

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

0.34

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

7.3

Mortality
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.69

Mortality
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 0.5 g 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)

> 202

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.7

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.01

Rat SF=100

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

0.02

Rat SF=100

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

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

0.01

Rat SF=100

Dermal penetration studies (%)

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders or residents identified

Occupational

No unacceptable risks to operators or other farm workers identified

European MRLs

EU MRL pesticide database

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H301, H317, H332, H373
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R20, R22, R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

tebufenpyrad

French

tebufenpyrad

German

Tebufenpyrad

Danish

tebufenpyrad

Italian

tebufenpirad

Spanish

tebufenpirad

Greek

Polish

tebufenpyrad

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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