| cyanazine |
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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 
for cyanazine
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
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Sweden |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | - |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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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 (g mol-1) | 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 | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Supplied in a wide range of formulations including suspension concentrates, wettable powders, granules & water-dispersible powders. | |||
ENVIRONMENTAL FATE
for cyanazine
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 171 | K4 | Moderate | |
| Solubility - In organic solvents at 20oC (mg l-1) | 195000 | L3 - Acetone | - | |
| 45000 | L3 - Ethanol | - | ||
| 15000 | L3 - Benzene | - | ||
| 15000 | L3 - Hexane | - | ||
| Melting point (oC) | 168 | L3 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.26 X 1002 | Calculated | - |
| Log P | 2.1 | H4 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.29 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 12.9 | DW4 | - | |
| Note: Very weak acid | ||||
| Vapour pressure at 20oC (mPa) | 0.000213 | H4 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 6.60 X 10-06 | H4 | Non-volatile | |
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 |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 16 | K4 | Non-persistent |
| DT50 (lab at 20oC) | 16 | K4 | Non-persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| 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 | - |
| Note | Various grasses, n=3 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | Stable | L3 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | L3 | - |
| Note | Stable pH 5 to pH 9, hydrolysed by strong acids and alkalis | |||
| Water-sediment DT50 (days) | 84 | K4 | Moderately fast | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | G3 | Moderately mobile |
| Koc | 190 | |||
| Notes and range | Other sources: 30-427 mL/g (R3) | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 157 | P4 (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 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L2 Rat, 2 year | - |
| (ppm diet) | 12 | - | ||
| Birds - Acute LD50 (mg kg-1) | 400 | L3 Phasianidae | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 10 | L2 Rasbora heteromorpha | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.08 | P3 Oncorhynchus mykiss, 10 day | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 49 | J4 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 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.2 | F4 Scenedesmus quadricauda | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.009 | J4 Green algae | Moderate | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 100 | L3 | 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 | 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
for cyanazine
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | 288 | F4 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | L3 Rabbit | - | |
| Mammals - Inhalation LC50 (mg l-1) | 2.46 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | - | - | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | - | - | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | Non-statutory WHO drinking water guideline 0.0006 mg/L | UK EA QS database, 2018 | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
|
A0; B0; C0; D0; E3 |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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- |
- |
- |
- |
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| General human health issues | USEPA - possible human carcinogen | |||||||
| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : Yes, known to cause a problem  : No, known not to cause a problem  : Possibly, status not identified - : No data found |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Prevent generation of spray mists | |||
| CLP classification 2013 | Health: H302 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S37, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | cyanazine |
| French | cyanazine |
| German | Cyanazin |
| Danish | cyanazin |
| Italian | cianazina |
| Spanish | cianazina |
| Greek | cyanazine |
| Slovenian | cianazin |
| Polish | cyjanazyna |
| Swedish | cyanazin |
| Hungarian | cianazin |
| Dutch | cyanazin |
Record last updated: Tuesday 10 December 2019
Contact: aeru@herts.ac.uk