| anilazine (Ref: ENT 26 058) |
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SUMMARY
Anilazine is a fungicide that no longer has approval for use in the EU. 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. GENERAL INFORMATION 
for anilazine
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
Efficacy & activity: -
Availability status: Obsolete
Introduction & key dates: circa 1955
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | - |
| 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: USA
Chemical structure:
| Isomerism | - |
| Chemical formula | C9H5Cl3N4 |
| Canonical SMILES | C1=CC=C(C(=C1)NC2=NC(=NC(=N2)Cl)Cl)Cl |
| Isomeric SMILES | No data |
| 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 group | Triazine | |||
| 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 | |||
| Molecular mass (g mol-1) | 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) | M8 | |||
| Examples of recorded resistance | - | |||
| Physical state | White to light brown 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 | - | |||
ENVIRONMENTAL FATE
for anilazine
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 8 | B5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 90000 | B4 - Dichloromethane | - | |
| 1700 | B4 - n-Hexane | - | ||
| 40000 | B4 - Toluene | - | ||
| 8000 | B4 - Isopropanol | - | ||
| Melting point (oC) | 159 | Q3 | - | |
| Boiling point (oC) | Decomposes before boiling | V3 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | V3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.05 X 1003 | Calculated | - |
| Log P | 3.02 | B5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.7 | B5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | H4 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 8.20 X 10-04 | B5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.10 X 10-04 | H4 | Non-volatile | |
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 |
- | 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) | 1 | B5 | Non-persistent |
| DT50 (lab at 20oC) | 1 | B4 | Non-persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| 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 | Stable |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 15 | K3 | Non-persistent |
| Note | - | |||
| Water-sediment DT50 (days) | 1 | K4 | Fast | |
| Water phase only DT50 (days) | 1 | K4 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | H3 | Slightly mobile |
| Koc | 2000 | |||
| Notes and range | Best available data | |||
| Freundlich | Kf | 20.6 | B5 | Slightly mobile |
| Kfoc | 1980 | |||
| 1/n | 0.86 | |||
| Notes and range | UK dossier Kf range 9.2-37.9 mL/g, Kfoc range 1438-2724 mL/g, 1/n - no data, Soils=4 | |||
| pH sensitivity | No | |||
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 210 | P4 | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 4570 | B5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 42 | B5 Rat | High |
| (ppm diet) | 500 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | B5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.095 | B5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.56 | B5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.058 | F3 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) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 1.02 | B5 Scenedemus subspicatus | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 1 | Q2 Unknown species | Moderate | |
| 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 | 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) | 1000 | B5 | Moderate | |
| Earthworms - Chronic NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms | Acute LC50 (mg kg-1) | 2938 | B4 Folsomia candida, as LC50 | - | Chronic NOEC (mg kg-1) | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 1000 | LC50 as mg kg-1 soil B4 Calathus fuscipes |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: Chronic effect Carbon mineralisation: No significant adverse effect |
B4 Dose: 100 mg kg-1 soil |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for anilazine
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) | 4570 | B5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | AC4 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.25 | AC4 Rat, 4 hr | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.1 | A5 / UK ACP 1999 | - | |
| 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 | [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 | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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A0; B0; C0; D0; E0 | - |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Toxic by inhalation, skin absorption, and/or ingestion | |||||||
| 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 |
Incompatible with oils and alkaline materials | |||
| CLP classification 2013 | Health: H315, H319 Environment: H400, H410 |
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| EC Risk Classification |
Xi - Irritant: R36/38 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S22, S60, S61 | |||
| WHO Classification | O | - | Obsolete substance | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | anilazine |
| French | anilazine |
| German | Anilazin |
| Danish | anilazin |
| Italian | anilazina |
| Spanish | anilazina |
| Greek | anilazine |
| Slovenian | anilazin |
| Polish | anilazyna |
| Swedish | - |
| Hungarian | - |
| Dutch | anilazine |
Record last updated: Monday 02 March 2020
Contact: aeru@herts.ac.uk