Cyanazine	Last updated: 22/12/2020
(Also known as: WL 19805; DW 3418)

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SUMMARY

Cyanazine is a triazine herbicide approved for use in the EU and many other countries. It is moderately soluble in water and many organic solvents and it is relatively volatile. It is not persistent in soil systems but can often be persistent in water. It is moderately toxic to mammals and may have serious adverse health effects if ingested as it is a neurotoxin, a suspected endocrine disrupter and a development/reproduction toxin. Cyanazine is moderately toxic to most fauna and flora.

GENERAL INFORMATION

Description	A pre-emergence herbicide used for general weed control includings grasses and broad-leaved weeds in a range of crops
Example pests controlled	Nightshade; Bindweed; Chickweed; Clover; Crowsfoot; Docks; Plantain; Sorrel; Sowthistle; Stinging nettle; Deadnettle
Example applications	Vegetables including peas, chickpeas, beans, lentils, onions; Potatoes; Sweetcorn
Efficacy & activity	-
Availability status	Current
Introduction & key dates	circa 1967

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	Sweden
Date EC 1107/2009 inclusion expires	Expired
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

Also used in	Australia

Chemical structure

Isomerism	-
Chemical formula	C₉H₁₃ClN₆
Canonical SMILES	CCNC1=NC(=NC(=N1)Cl)NC(C)(C)C#N
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	MZZBPDKVEFVLFF-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C9H13ClN6/c1-4-12-7-13-6(10)14-8(15-7)16-9(2,3)5-11/h4H2,1-3H3,(H2,12,13,14,15,16)
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cyanazine	-

General status

Pesticide type	Herbicide
Substance group	Triazine
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Selective, systemic with contact and residual action. Inhibits photosynthesis (photosystem II).
CAS RN	21725-46-2
EC number	244-544-9
CIPAC number	230
US EPA chemical code	100101
PubChem CID	30773
Molecular mass	240.69
PIN (Preferred Identification Name)	2-{[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino}-2-methylpropanenitrile
IUPAC name	2-(4-chloro-6-ethylamino-1,3,5-triazin-2-ylamino)-2-methylpropiononitrile
CAS name	2-((4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl)amino)-2-methylpropanenitrile
Other status information	Potential groundwater contaminant; Chemical subject to PIC regulations
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	C1
Herbicide Resistance Classification (WSSA)	5
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Kochia scoparia
Physical state	White crystals
Related substances & organisms	atrazine bentazone 2,4-D diflufenican

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Fortrol Bladex Payze Blanchol
Example products using this active	Syngenta Shell Chemical Co DuPont BASF
Formulation and application details	Supplied in a wide range of formulations including suspension concentrates, wettable powders, granules & water-dispersible powders

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		171	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)		195000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Acetone	-
		45000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Ethanol	-
		15000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Benzene	-
		15000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Hexane	-
Melting point (°C)		168	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.26 X 1002	Calculated	-
	Log P	2.1	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	Low
Bulk density (g ml⁻¹)		1.29	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Dissociation constant pKa) at 25 °C		12.9	DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. MS in preparation 4 = Verified data	-
		Very weak acid
Vapour pressure at 20 °C (mPa)		0.000213	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		6.60 X 10-06	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)	16	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Non-persistent
	DT₅₀ (lab at 20 °C)	16	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Non-persistent
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Other sources: DT₅₀ 12-25 days (R3)
Dissipation rate RL₅₀ on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	4.0	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	Note	Various grasses, n=3
Aqueous photolysis DT₅₀ (days) at pH 7	Value	Stable	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Stable
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Stable
	Note	Stable pH 5 to pH 9, hydrolysed by strong acids and alkalis
Water-sediment DT₅₀ (days)		84	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Moderately fast
Water phase only DT₅₀ (days)		-	-	-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	G3 G = Extension Toxicology network database EXTOXNET (click here ) 3 = Unverified data of known source	Moderately mobile
	Koc	190
	Notes and range	Other sources: 30-427 mL g⁻¹ (R3)
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		2.07	Calculated	Transition state
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	6.25 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		Low	Calculated	-
Potential for loss via drain flow		Moderately mobile	Calculated	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	157	P4 P = Other governments and regulators 4 = Verified data (Other literature Log BCF range 2.3-4.1 (R3))	Threshold for concern
	CT₅₀ (days)	Not available		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		288	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rat 2 year	-
	(ppm diet)	12		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		400	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Phasianidae	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		10	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rasbora heteromorpha	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.08	P3 P = Other governments and regulators 3 = Unverified data of known source Oncorhynchus mykiss 10 day	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		49	J4 J = Pesticide Action Network database (click here ) 4 = Verified data 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)		0.051	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 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		0.2	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Scenedesmus quadricauda	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		0.009	J4 J = Pesticide Action Network database (click here ) 4 = Verified data Green algae	Moderate
Honeybees (Apis spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	100	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Moderate
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	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)		600	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	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	-	-	-
	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)		288	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		2.46	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
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	-
European MRLs		EU MRL pesticide database
Drinking Water Standards		Non-statutory WHO drinking water guideline 0.0006 mg l⁻¹	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes UK EA QS database 2018	-
Drinking Water MAC (μg l⁻¹)		-	-	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor ?Possibly, status not identified 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 ; E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative ✓Yes, known to cause a problem Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ✓Yes, known to cause a problem XNo, known not to cause a problem ✓Yes, known to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser ✓Yes, known to cause a problem No data found No data found Eye irritant Phototoxicant   No data found No data found
General human health issues		USEPA - possible human carcinogen

Handling issues

Property	Value and interpretation
General	Prevent generation of spray mists
CLP classification 2013	Health: H302 Environment: H400, H410
EC Risk Classification	Xn - Harmful: R22 N - Dangerous for the environment: R50, R53
EC Safety Classification	S2, S37, S60, S61
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	cyanazine
French	cyanazine
German	Cyanazin
Danish	cyanazin
Italian	cianazina
Spanish	cianazina
Greek	cyanazine
Polish	cyjanazyna
Swedish	cyanazin
Hungarian	cianazin
Dutch	cyanazin

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Record last updated:	22/12/2020
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