Diofenolan (Ref: CGA 059205)

Diofenolan (Ref: CGA 059205)	Last updated: 16/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

Substance used for the control of scale insects and other insect pests

Example pests controlled

Scale insects including San José scale, red coconut scale; Citrus butterfly; Whiteflies

Example applications

Fruit including grapes, olives, citrus, peach; Nuts; Ornamentals

Efficacy & activity

Availability status

Unknown

Introduction & key dates

1994, first reported

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

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not aplicable

Listed in EU database

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

Diofenolan is a molecule with two chiral centres. TThe technical material is an reaction mixture of various isomers.

Chemical formula

C₁₈H₂₀O₄

Canonical SMILES

CCC1OCC(O1)COC2=CC=C(C=C2)OC3=CC=CC=C3

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ZDOOQPFIGYHZFV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H20O4/c1-2-18-20-13-17(22-18)12-19-14-8-10-16(11-9-14)21-15-6-4-3-5-7-15/h3-11,17-18H,2,12-13H2,1H3/t17-,18+/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Insect Growth Regulator

Substance group

Diphenyl ether

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Insect growth retardant, moulting inhibitor with juvenile hormone activity

CAS RN

63837-33-2

EC number

CIPAC number

US EPA chemical code

007703

PubChem CID

4578030

Molecular mass

300.35

PIN (Preferred Identification Name)

Mix of: rac-(2R,4S)-2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane (50%–80%) and rac-(2R,4R)-2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane (50%–20%)

IUPAC name

Mix of: (2RS,4SR)-4-(2-ethyl-1,3-dioxolan-4-ylmethoxy)phenyl phenyl ether (50%–80%) and (2RS,4RS)-4-(2-ethyl-1,3-dioxolan-4-ylmethoxy)phenyl phenyl ether (50%–20%)

CAS name

2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not known

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Pale yellow viscous liquid

Formulations

Property

Value

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

Aware
Arbor
Context

Example products using this active

Novartis
Ciba-Geigy AG

Formulation and application details

Usually supplied as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

4.9

Low

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

Miscible

n-Hexane

Miscible

Toluene

Miscible

Methanol

Melting point (°C)

Boiling point (°C)

250

Degradation point (°C)

Flashpoint (°C)

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

2.24 X 10⁰⁴

Calculated

Log P

4.35

High

Bulk density (g ml⁻¹)

1.141

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.011

Low volatility

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

6.74 X 10^-03

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

3.0

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature states 2 to 10 days

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

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

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)

> 1000

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.5

Daphnia magna

Moderate

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

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

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)

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)

> 96.0

Moderate

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

> 96

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)

204

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

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

; ; ; ;

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

No further information available

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

EC Risk Classification

EC Safety Classification

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

diofenolan

French

diofenolane

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	16/01/2021
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