| azafenidin |
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SUMMARY
Azafenidin is a triazolinone herbicide that does not have EU approval for use. It has a low solubility, is semi-volatile and moderately persistent in soil. It does not persist in water in daylight conditions. Whilst the pesticide is not highly toxic to mammals there is a risk of bioaccumulation. Azafenidin shows a low to moderate toxicity to birds, most aquatic organisms and honeybees. GENERAL INFORMATION 
for azafenidin
Description: A pre-emergence herbicide used to control broad-leaved weeds and grasses
Example pests controlled: Common groundsel; Fleabane; Spurge; Knotsweed; Lambsquarter; Bermuda grass; Annual ryegrass; Johnson grass
Example applications: Eucalyptus; Pineapple; Citrus; Melons; Grapes
Efficacy & activity: -
Availability status: Current
Introduction & key dates: circa 1997
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Spain |
| 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 | None |
| Chemical formula | C15H13Cl2N3O2 |
| Canonical SMILES | C#CCOC1=C(C=C(C(=C1)N2C(=O)N3CCCCC3=N2)Cl)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | XOEMATDHVZOBSG-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3 |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |||
| Substance group | Triazolinone | |||
| Minimum active substance purity | 97% | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Inhibition of protoporphyrinogen oxidase, selective with some residual effect | |||
| CAS RN | 68049-83-2 | |||
| EC number | - | |||
| CIPAC number | 606 | |||
| US EPA chemical code | 119016 | |||
| PubChem CID | 443029 | |||
| Molecular mass (g mol-1) | 338.19 | |||
| PIN (Preferred Identification Name) | 2-[2,4-dichloro-5-(prop-2-yn-1-yloxy)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one | |||
| IUPAC name | 2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one | |||
| CAS name | 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | E | |||
| Herbicide Resistance Classification (WSSA) | 14 | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | - | |||
| Physical state | White to brown powder depending on purity | |||
| 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 | Usually supplied as wettable granules. | |||
ENVIRONMENTAL FATE
for azafenidin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 16 | L3 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | - | - | - | |
| Melting point (oC) | 168 | V3 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 5.01 X 1002 | Calculated | - |
| Log P | 2.7 | L3 | Moderate | |
| Bulk density (g ml-1)/Specific gravity | 1.4 | L3 | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 1.00 X 10-06 | L3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | - | - | - | |
GUS leaching potential index  |
2.79 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 2.34 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| 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) | 67 | DW4 | Moderately persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | 25 | L3 | Non-persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | 169 | L3 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Literature DT50 studies range 20-70 days | |||
| 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 | 0.5 | L3 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | L3 | - |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | L3 | Moderately mobile |
| Koc | 298 | |||
| Notes and range | Best available data | |||
| 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) | Low risk | F3 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | L3 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L3 Rat | - |
| (ppm diet) | 50 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2250 | L3 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 33 | L3 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 38 | L3 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) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 0.00094 | L3 Raphidocelis subcapitata | High | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | - | - | - |
| Oral acute 48 hour LD50 (μg bee-1) | > 20 | L3 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | - | - | - | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| 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 azafenidin
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) | > 5000 | L3 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | R4 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 5.3 | R4 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 Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | No further information available | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
No information available | |||
| CLP classification 2013 | Health: H360Df, H373 Environment: H400, H410 |
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| EC Risk Classification |
Reproduction risk category 2 and 3: R61, R62 T - Toxic: R48/22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S45, S53, S61, S60 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | azafenidin |
| French | azafenidine |
| German | Azafenidin |
| Danish | azafenidin |
| Italian | azafenidin |
| Spanish | azafenidin |
| Greek | azafenidin |
| Slovenian | azafenidin |
| Polish | azafenidyna |
| Swedish | - |
| Hungarian | azafenidin |
| Dutch | azafenidin |
Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk