Clofentezine (Ref: NC 21314)

Clofentezine (Ref: NC 21314)	Last updated: 12/01/2021
(Also known as: bisclofentazin)

GENERAL INFORMATION

Description

A selective ovicidal tetrazine acaricide for use in a range of crops including fruit and ornamentals

Example pests controlled

Spidermites (eggs and adults) including the two-spotted spider mite, European red mite, McDaniel spider mite

Example applications

Fruit including apples, pears, peaches, nectarines, raspberries, strawberries, citrus; Tomatoes; Eggplant; Ornamentals including nursery stock

Efficacy & activity

Efficacy has been established via development trials and commercial use over a number of years,

Availability status

Current

Introduction & key dates

2001

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Netherlands

Date EC 1107/2009 inclusion expires

31/12/2021

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

Australia, USA

Chemical structure

Isomerism

Chemical formula

C₁₄H₈Cl₂N₄

Canonical SMILES

C1=CC=C(C(=C1)C2=NN=C(N=N2)C3=CC=CC=C3Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UXADOQPNKNTIHB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H8Cl2N4/c15-11-7-3-1-5-9(11)13-17-19-14(20-18-13)10-6-2-4-8-12(10)16/h1-8H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
clofentezine	-

General status

Pesticide type

Acaricide

Substance group

Tetrazine

Minimum active substance purity

780 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Specific with contact action and long residual activity

CAS RN

74115-24-5

EC number

277-728-2

CIPAC number

418

US EPA chemical code

125501

PubChem CID

73670

Molecular mass

303.15

PIN (Preferred Identification Name)

3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine

IUPAC name

3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine

CAS name

3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine

Other status information

Has been detected in Swedish air monitoring programmes.

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

10A

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Panonychus ulmi, Tetranychus urticae

Physical state

Magenta crystals

Formulations

Property

Value

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

Apollo 50 SC
Vivaro
Panatac

Example products using this active

Makhteshim-Agan
Ypsilon SA
Scotts
FBC

Formulation and application details

Usually supplied as a soluble concentrate or wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0342

Low

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

9300

Acetone

5670

Ethyl acetate

490

Ethanol

5000

Xylene

Melting point (°C)

183

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

190

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.23 X 10⁰⁴

Calculated

Log P

4.09

High

Bulk density (g ml⁻¹)

1.52

Dissociation constant pKa) at 25 °C

Unstable- cannot be determined

Vapour pressure at 20 °C (mPa)

6.0 X 10^-04

Low volatility

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

0.00536

Non-volatile

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

Neutral solution 534.5nm = 465
Acidic solution: 526.3nm=636
Basic solution: 536.2=220

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

69.8

Moderately persistent

DT₅₀ (lab at 20 °C)

69.8

Moderately persistent

DT₅₀ (field)

63.0

Moderately persistent

DT₉₀ (lab at 20 °C)

426

Very persistent

DT₉₀ (field)

209.7

DT₅₀ modelling endpoint

67.2

nomalised geometric mean

Note

EU 2018 dossier (not normalised) lab studies DT₅₀ range 16.9-133 days, DT₉₀ range 56->1000 days, field studies DT₅₀ range 52.9-71.3 days, DT₉₀ range 176-237 days, Soils=3

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

5.88

Moderately fast

Note

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

Value

3.1

Non-persistent

Note

Water-sediment DT₅₀ (days)

9.6

Fast

Water phase only DT₅₀ (days)

2.1

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

75.7

Non-mobile

K_foc

6303

¹/_n

0.87

Notes and range

EU 2018 dossier K_f range 40.2-245.9 mL g⁻¹. K_foc range 3753.7-17318.6 mL g⁻¹, ¹/_n range 079-0.97, Soils=4

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.36

Calculated

Low leachability

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

Value

8.41 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-chlorobenzoic acid (Ref: AE-C500233)

Soil

0.109

Major fraction, Relevant

hydrazide-hydrazone (Ref: AE C593600)

Soil

0.130

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

di-hydro-clofentazine

NC 22505

Plant

2-chlorobenzonitrile (Ref: AE F023666)

Plants

2-chlorobenzamide (Ref: AE F092117)

Plants

2-chlorobenzyl alcohol

Plant

4-hydroxy-clofentazine

Animal

3-hydroxy-clofentazine

Animal

5-hydroxy-clofentazine

Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

248

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5200

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

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

> 27.8

Unknown species Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 6501

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 4000 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

7.62

Colinius virginianus NOEC

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.01

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.007

Oncorhynchus mykiss 97 day

High

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

> 71.6

Daphnia magna

Moderate

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

0.05

Daphnia magna

Moderate

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

0.003

Americamysis bahia as 28d NOEC

High

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

> 76.4

Chironomus riparius 48 hr

Moderate

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

0.37

Chironomus riparius

Moderate

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

0.5

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)

34.0

Selenastrum capricornutum

Low

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)

> 84.5

Apis mellifera

Moderate

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

> 252.6

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)

> 215

Eisenia foetida corr

Moderate

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

2.0

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

> 80

Folsomia candida 28d corr

Other arthropod (1)

LR₅₀ g ha⁻¹

36.2

Aphidius rhopalosiphi

% Effect

Mortality [Dose: 0.3 g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

300

> Mortality
Typhlodromus pyri

% Effect

Mortality [Dose: 0.3 g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 2.39 mg kg⁻¹ 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)

> 5200

Rat

Low

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

2100

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.2

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.02

Rat 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)

None allocated

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

0.01

Rat SF=100

Dermal penetration studies (%)

2.1-19.9

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders determined

Occupational

Potential risk to operators and other farm workers - PPE advised

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.01

EU Dir 89/778/EC limit; Calc MAC=0.06 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

General human health issues

May reduce blood haemoglobin levels
Possible thyroid and liver toxicant
USEPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H312
Environment: H400, H412

EC Risk Classification

N - Dangerous for the environment: R52, R53

EC Safety Classification

S60, S61

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

clofentezine

French

clofentezine

German

Clofentezin

Danish

clofentezin

Italian

clofentezine

Spanish

clofentezin

Greek

Polish

chlofentezyna

Swedish

klofentezin

Hungarian

klofentezin

Dutch

clofentezin

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