Anilazine (Ref: ENT 26 058)

Anilazine (Ref: ENT 26 058)	Last updated: 21/08/2024
(Also known as: NCI C08684; triasyn; anivaline; zinochlor ; dyrene; B-622; NSC-3851)

SUMMARY

Anilazine is a largely obsolete fungicide. It has a low aqueous solubility, volatile and presents a low risk of leaching to groundwater. Whilst it is not highly toxic to humans there are some concerns regarding its potential to bioaccumulate. It is highly toxic to fish and moderately toxic to most other aquatic organisms, birds, 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: Fish acute ecotoxicity: High	Human health High alert: Genotoxic

GENERAL INFORMATION

Description

An obsolete fungicide once used to control various fungal pathogens including blights and Botrytis on fruit and other crops

Example pests controlled

Late blights; Leaf spots; Anthracnose; Downy mildew; Botrytis; Alternaria

Example applications

Fruit including blackberry, cranberry, raspberry, blueberry and melon; Celery; Cucumber; Garlic and onions; Potato; Pumpkin; Cereals; Coffee

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

circa 1955, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

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

Expired

EU Candidate for substitution (CfS)

Not applicable

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

USA

Chemical structure

Isomerism

None

Chemical formula

C₉H₅Cl₃N₄

Canonical SMILES

C1=CC=C(C(=C1)NC2=NC(=NC(=N2)Cl)Cl)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

IMHBYKMAHXWHRP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H5Cl3N4/c10-5-3-1-2-4-6(5)13-9-15-7(11)14-8(12)16-9/h1-4H,(H,13,14,15,16)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
anilazine	-

General status

Pesticide type

Fungicide

Substance groups

Triazine fungicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Non-systemic with protective action, enzyme inhibitor. Multi-site activity.

CAS RN

101-05-3

EC number

202-910-5

CIPAC number

294

US EPA chemical code

080811

PubChem CID

7541

CLP index number

613-053-00-5

Molecular mass

275.53

PIN (Preferred Identification Name)

4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine

IUPAC name

4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine

CAS name

4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine

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)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

M08

Examples of recorded resistance

Physical state

White to light brown crystals

Formulations

Property

Value

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

Scotts Company
Bayer CropScience
Nippon
Mobbay

Example products using this active

Kemate
Triasym
Direz
Dyrene
Triazin Jet
Botrysan
Triasyn
Agrico Lawn Fungicide

Formulation and application details

Supplied mainly as a wettable or flowable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

90000

Dichloromethane

1700

n-Hexane

40000

Toluene

8000

Isopropanol

Melting point (°C)

159

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

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

1.05 X 10⁰³

Calculated

Log P

3.02

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.7

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

8.20 X 10^-04

Low volatility

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

1.10 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Lab studies (1) DT₅₀: 15 hours (2) DT₅₀: 34 hours

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

180

Stable

Note

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

Value

Non-persistent

Note

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately 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.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

2000

Notes and range

Best available data

Freundlich

K_f (mL g⁻¹)

20.6

Slightly mobile

K_foc (mL g⁻¹)

1980

¹/_n

0.86

Notes and range

UK dossier K_f range 9.2-37.9 mL g⁻¹, K_foc range 1438-2724 mL g⁻¹, ¹/_n - no data, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.00

Calculated

Low leachability

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

Value

1.39 X 10^-04

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

Bio-concentration factor

BCF (l kg⁻¹)

210

Threshold for concern

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

4,6-dihydroxy-N-(2-chlorophenyl)-2-amino-1,3,-5-triazine (Ref: dihydroxy-anilazine)

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-(2-chloroanilino)-s-triazinodione

Human

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

4570

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

500

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

1000

Moderate

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

Soil micro-organisms

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

Dose: 100 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

2938

Folsomia candida as LC₅₀

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis 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)

100

Moderate

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

Chronic

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 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)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

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)

0.095

Oncorhynchus mykiss

High

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

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

7.27

Danio rerio

Moderate

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

0.56

Daphnia magna

Moderate

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

0.058

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

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

1.02

Scenedesmus subspicatus

Moderate

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

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

4570

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.25

Rat 4 hr

Other Mammal toxicity endpoints

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

0.1

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

[Since substance is no longer used as a fungicide in the most of the developed world consumer exposure is expected to be low]

Exposure Routes

Public

Since substance is no longer used as a fungicide in the most of the developed world occupational exposure is expected to be low

Occupational

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

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

No data found

General human health issues

Toxic by inhalation, skin absorption, and/or ingestion

Handling issues

Property

Value and interpretation

General

Incompatible with oils and alkaline materials
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H315, H319
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

anilazine

French

anilazine

German

Anilazin

Danish

anilazin

Italian

anilazina

Spanish

anilazina

Greek

anilazine

Polish

anilazyna

Swedish

Hungarian

Dutch

anilazine

Norwegian

Record last updated:	21/08/2024
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