Anilazine (Ref: ENT 26 058)	Last updated: 13/01/2023
(Also known as: NCI-C08684; triasyn; anivaline; zinochlor ; dyrene; B-622; NSC-3851)

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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 Moderate alert: Possible Reproduction/development effects

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

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
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	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

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 Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	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)		8	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		90000	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data Dichloromethane	-
		1700	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data n-Hexane	-
		40000	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data Toluene	-
		8000	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data Isopropanol	-
Melting point (°C)		159	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	-
Boiling point (°C)		Decomposes before boiling	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.05 X 1003	Calculated	-
	Log P	3.02	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	High
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		1.7	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	-
Dissociation constant pKa) at 25 °C		Not applicable	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	-
		No dissociation
Vapour pressure at 20 °C (mPa)		8.20 X 10-04	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		1.10 X 10-04	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	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)	1	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Non-persistent
	DT₅₀ (lab at 20 °C)	1	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data	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 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	180	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data	Stable
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	15	K3 K = Research datasets, e.g. Pandora, Demetra 3 = Unverified data of known source	Non-persistent
	Note	-
Water-sediment DT₅₀ (days)		1	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Fast
Water phase only DT₅₀ (days)		1	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Moderately fast

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	H3 H = The US ARS pesticide properties database (click here ) 3 = Unverified data of known source	Slightly mobile
	Koc	2000
	Notes and range	Best available data
Freundlich	Kf	20.6	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Slightly mobile
	Kfoc	1980
	1/n	0.86
	Notes and range	UK dossier Kf range 9.2-37.9 mL g⁻¹, Kfoc range 1438-2724 mL g⁻¹, 1/n - no data, Soils=4
pH sensitivity		No

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	-
Bio-concentration factor	BCF (l kg⁻¹)	210	P4 P = Other governments and regulators 4 = Verified data	Threshold for concern
	CT₅₀ (days)	Not available		-

Known soil metabolites

Metabolite	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	Metabolising enzymes
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	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Rat	Low
Mammals - Short term dietary NOEL	(mg kg⁻¹)	42	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Rat	High
	(ppm diet)	500		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		> 2000	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes 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	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		Nitrogen mineralisation: Chronic effect Carbon mineralisation: No significant adverse effect	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data Dose: 100 mg kg⁻¹ soil	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	2938	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data 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	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	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 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	-
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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.095	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.56	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		0.058	F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source Daphnia magna	Moderate
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	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Scenedemus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		1	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source Unknown species	Moderate
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	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)		4570	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		5000	AC4 AC = EC Joint Research Centre ESIS European Chemical Substance Information Systems including EINECS, now integrated with the database provided by the European Chemicals Agency (ECHA) (click here ) 4 = Verified data Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		0.25	AC4 AC = EC Joint Research Centre ESIS European Chemical Substance Information Systems including EINECS, now integrated with the database provided by the European Chemicals Agency (ECHA) (click here ) 4 = Verified data Rat 4 hr	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		0.1	A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes UK ACP 1999	-
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 XNo, known not to cause a problem A0 A = Chromosome aberration (EFSA database) 0 = No data ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E1 E = Unspecified genotoxicity type (miscellaneous data source) 1 = Positive No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ?Possibly, status not identified XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser No data found ✓Yes, known to cause a problem ✓Yes, known to cause a problem Eye irritant Phototoxicant   ✓Yes, known to cause a problem 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 autoignite; Not highly flammable
CLP classification 2013	Health: H315, H319 Environment: H400, H410
WHO Classification	O (Obsolete substance)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	anilazine
French	anilazine
German	Anilazin
Danish	anilazin
Italian	anilazina
Spanish	anilazina
Greek	anilazine
Polish	anilazyna
Swedish	-
Hungarian	-
Dutch	anilazine

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Record last updated:	13/01/2023
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