Bifenazate

Bifenazate	Last updated: 16/02/2021
(Also known as: D 2341; HSDB 7002)

SUMMARY

Bifenazate is an insecticide approved for use in the EU. It has a low water solubility, volatile and would not be expected to leach to groundwater. Bifenate 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.

GENERAL INFORMATION

Description

An effective, new 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 (RAR active)

Date COPR inclusion expires

31/07/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved (RAR active)

Dossier rapporteur/co-rapporteur

Sweden/Italy

Date EC 1107/2009 inclusion expires

31/07/2021

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

None

Chemical formula

C₁₇H₂₀N₂O₃

Canonical SMILES

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

Isomeric SMILES

No data

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 group

Hydrazine carboxylate

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

CAS RN

149877-41-8

EC number

442-820-5

CIPAC number

736

US EPA chemical code

000586

PubChem CID

176879

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

20D

Fungicide Resistance Classification (FRAC)

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

Floramite SC
Acramite

Example products using this active

Certis
Chemtura Corp.

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)

Not expected to self-ignite; Not highly flammable

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

2.51 X 10⁰³

Calculated

Log P

3.4

High

Bulk density (g ml⁻¹)

1.31

Dissociation constant pKa) at 25 °C

12.94

Strong base

Vapour pressure at 20 °C (mPa)

1.33 X 10^-02

Low volatility

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

1.01 X 10^-03

Non-volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.855

Major fraction, Relevant

4-methoxybiphenyl (Ref: D-1989)

Soil

0.333

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

Ref: D-9963

Water (Photolysis)

4-hydroxybiphenyl

Rat

4,4-biphenyl

Rat

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

Water (Photolysis)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.58

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.017

Oncorhynchus mykiss

Moderate

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

0.5

Daphnia magna

Moderate

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

0.15

Daphnia magna

Moderate

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

0.058

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)

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

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

Non-target plants

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

0.3

Skeletonema costatum

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)

8.50

Apis mellifera

Moderate

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)

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 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)

> 429

Eisenia foetida

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Moderately harmful

Parasitoids

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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

JMPR 2006

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

Not allocated

JMPR 2006

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

Rat 90 day SF=100

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

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

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 Code is usually 9

CLP classification 2013

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

EC Risk Classification

Xn - Harmful: R43
Xi - Irritant: R36

EC Safety Classification

S26, S36/37

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

bifenazate

French

bifenazate

German

Bifenazat

Danish

bifenazat

Italian

bifenazate

Spanish

bifenazato

Greek

Polish

bifenazat

Swedish

bifenazat

Hungarian

Dutch

Record last updated:	16/02/2021
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