Bifenazate

Bifenazate	Last updated: 15/03/2024
(Also known as: D 2341; HSDB 7002)

SUMMARY

Bifenazate is an insecticide used for mite control. It has a low water solubility, volatile and would not be expected to leach to groundwater. Bifenazate is also not expected to persist in soil or water systems. It is highly toxic to mammals and a recognised skin, eye and respiratory system irritant. It is moderately toxic to most aquatic organisms, honeybees and earthworms.

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	Ecotoxicity High alert: Birds chronic ecotoxicity: High	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

An effective pesticide for phytophagous mite control

Example pests controlled

Spider mites; Pecan leaf mites; Pacific spider mites; European red mites; Brown almond mite; Six-spotted spider mite

Example applications

Greenhouse crops; Nursery crops; Landscaped areas; Hops; Avocado; Curcubits; Apples & pears; Quince; Egg plants; Cucumbers; Water melon; Strawberries; Tomatoes

Efficacy & activity

Availability status

Current

Introduction & key dates

1996, first introduced; 1999, registered USA; 2000, registered UK

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2029

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/Italy

Date EC 1107/2009 inclusion expires

30/06/2037

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

Australia, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₇H₂₀N₂O₃

Canonical SMILES

CC(C)OC(=O)NNC1=C(C=CC(=C1)C2=CC=CC=C2)OC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

VHLKTXFWDRXILV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H20N2O3/c1-12(2)22-17(20)19-18-15-11-14(9-10-16(15)21-3)13-7-5-4-6-8-13/h4-12,18H,1-3H3,(H,19,20)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Carbazate insecticide; Carbazate acaricide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - Toluene 0.7 g kg⁻¹

Substance origin

Synthetic

Mode of action

Neuronal inhibitor, non-systemic having contact and residual action. Mitochondrial complex III electron transport inhibitor - at Qo site.

CAS RN

149877-41-8

EC number

442-820-5

CIPAC number

736

US EPA chemical code

000586

PubChem CID

176879

CLP index number

No data found

Molecular mass

300.35

PIN (Preferred Identification Name)

propan-2-yl 2-(4-methoxy[1,1'-biphenyl]-3-yl)hydrazinecarboxylate

IUPAC name

isopropyl 3-(4-methoxybiphenyl-3-yl)carbazate

CAS name

1-methylethyl 2-(4-methoxy[1,1'-biphenyl]-3-yl)hydrazinecarboxylate

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)

20D

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Tetranychus urticae

Physical state

White to beige coloured crystalline solid as technical material, white as the pure substance

Formulations

Property

Value

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

Certis
Chemtura Corp.

Example products using this active

Floramite SC
Acramite

Formulation and application details

Often supplied as a suspension concentrated which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.06

Low

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

210700

Acetone

102000

Ethyl acetate

44700

Methanol

24700

Toluene

Melting point (°C)

122

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

240

Flashpoint (°C)

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

2.51 X 10⁰³

Calculated

Log P

3.4

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.31

Dissociation constant pKa) at 25 °C

12.94

Strong base

Vapour pressure at 20 °C (mPa)

2.2 X 10^-06

Low volatility

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

2.76 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

Neutral solution: 206nm = 272686, 232nm = 25058, 264nm = 12413, 290nm = 6186 shoulder

Surface tension (mN m⁻¹)

61.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.69

Non-persistent

DT₅₀ (lab at 20 °C)

0.69

Non-persistent

DT₅₀ (field)

4.8

Non-persistent

DT₉₀ (lab at 20 °C)

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier (RAR 2016) lab studies DT₅₀ range <1 - 6.0 days, DT₉₀ range 0.3-12.3 days n=4

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.7

Note

Tea shoots; Strawberries; Range 1.2-8.2 days, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.85

Fast

Note

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

Value

0.51

Non-persistent

Note

pH sensitive: DT₅₀ 8.2 days at pH 4, 4.8 days at pH 5, 0.51 days at pH 7 and 0.04 days at pH 9 all at 25 °C

Water-sediment DT₅₀ (days)

0.045

Fast

Water phase only DT₅₀ (days)

0.45

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.

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

1778

Notes and range

Freundlich

K_f

7.0

Moderately mobile

K_foc

368

¹/_n

1.16

Notes and range

EU dossier (2016 RAR) K_f range 4.4-14.6 mL g⁻¹, K_foc range 243-628 mL g⁻¹, ¹/_n range 1.00-1.24, Soils=4

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.98

Calculated

Low leachability

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

Value

3.61 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

0.6

Calculated using the Atkinson method. Assumed 5.0E+05 OH/cm³, 24 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

diazinecarboxylic acid, 2-(4-methoxy-(1,1-biphenyl)-3-yl),1-methylethyl ester (Ref: D-3598)

Major fraction

0.855

4-methoxybiphenyl (Ref: D-1989)

Major fraction

0.333

1,8-dimethoxy-4,5-diphenyl-9H-carbazole

Major fraction

0.125

isopropyl 2,2-bis(4-methoxybiphenol-3-yl)hydrazinecarboxylate

Minor fraction

0.069

4-hydroxybiphenyl

Minor fraction

Anaerobic

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3,4-dihydroxy-[1,1'-biphenyl] (Ref: D-9472)

Surface water (Photolysis)

3-hydroxy-4-methoxy-[1,1'-biphenyl] (Ref: D-9963)

Surface water (Photolysis)

4-hydroxybiphenyl (Ref: A1530)

Rat

4,4-biphenyl

Rat

4-hydroxybiphenyl hydrogen sulphate

A1539 sulphate

4-hydroxy-bifenazate

4-OH- bifenazate

n-(4'-hydroxy-4-methoxybiphenyl-3-yl)diazenecarboxylic acid isopropyl ester

4-OH-D3598

bifenazate glucuronide

4-(4'-methoxyphenyl)phenol (Ref: D-9477)

1,8-dimethoxy-4,5-diphenyl-9H-carbazole

DDC

Surface water

isopropyl 2,2-bis(4-methoxybiphenol-3-yl)hydrazinecarboxylate

IBMHC

Surface water

diazinecarboxylic acid, 2-(4-methoxy-(1,1-biphenyl)-3-yl),1-methylethyl ester (Ref: D-3598)

Surface water; Sediment

4-methoxybiphenyl (Ref: D-1989)

D-1989

Surface water

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)

> 0.9

Dog

High

(ppm diet)

> 40

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

> 200

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

1036

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

686 mg kg feed⁻¹

Anas platyrhynchos

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

2.1

Anas platyrhynchos NOEL

High

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 429

Eisenia foetida

Moderate

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

9.75

Eisenia foetida

Moderate

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

307.7

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

8.50

Apis mellifera

Moderate

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

141

Apis mellifera

Low

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

0.350

Apis mellifera

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)

9.6

Bombus terrestris as mg l⁻¹

Moderate

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)

Beneficial insects (Lacewings) as % Mortality at dose 300 g ha⁻¹

< 50

Coccinella septempunctata

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

262

Aphidius rhopalosiphi

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

23.8

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.58

Lepomis macrochirus

Moderate

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

0.017

Oncorhynchus mykiss

Moderate

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

3.04

Danio rerio

Moderate

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

0.5

Daphnia magna

Moderate

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

0.15

Daphnia magna

Moderate

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

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

0.058

Americamysis bahia

High

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

> 1.0

Chironomus riparius EC₅₀

Moderate

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)

0.3

Skeletonema costatum

Moderate

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

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)

> 4.4

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.01

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

0.1

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

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

0.0036

Dermal penetration studies (%)

1-2

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Occupational exposure may occur through inhalation of dust and dermal contact

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

Mainly excreted as unchanged substance via bile

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Harmful if ingested

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317. H319, H373
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bifenazate

French

bifenazate

German

Bifenazat

Danish

bifenazat

Italian

bifenazate

Spanish

bifenazato

Greek

Polish

bifenazat

Swedish

bifenazat

Hungarian

Dutch

Norwegian

bifenazat

Record last updated:	15/03/2024
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