| fenarimol (Ref: EL 222) |
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GENERAL INFORMATION 
for fenarimol
Description: A foliar fungicide used to control a range of diseases including powdery mildew, dollar spot and snow mould
Example pests controlled: Powdery mildew, Dollar spot, Snow mould, Scab, leaf spot, Rusts
Example applications: Fruit including bananas, chrry, filberts, grapes, pears; Ornamental plants and trees; Turf
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1975, first reported; 1977, first introduced Lebanon
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | UK |
| 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, USA
Chemical structure:
| Isomerism | A chiral molecule existing in the R- and S-forms |
| Chemical formula | C17H12Cl2N2O |
| Canonical SMILES | C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)(C3=CN=CN=C3)O)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | NHOWDZOIZKMVAI-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Alpha-fenarimol | Isomer |  |
General status:
| Pesticide type | Fungicide | |||
| Substance group | Pyrimidine | |||
| Minimum active substance purity | 98% | |||
| Known relevant impurities | EU dossier - None declared | |||
| Substance origin | Synthetic | |||
| Mode of action | Systemic, curative and protective action. Disrupts membrane function. | |||
| CAS RN | 60168-88-9 | |||
| EC number | 262-095-7 | |||
| CIPAC number | 380 | |||
| US EPA chemical code | 206600 | |||
| PubChem CID | 43226 | |||
| Molecular mass (g mol-1) | 331.20 | |||
| PIN (Preferred Identification Name) | rac-(R)-(2-chlorophenyl)(4-chlorophenyl)(pyrimidin-5-yl)methanol | |||
| IUPAC name | (RS)-2,4'-dichloro-a-(pyrimidin-5-yl)benzhydryl alcohol | |||
| CAS name | α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol | |||
| Other status information | Chemical subject to PIC regulations | |||
| 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) | 3 | |||
| Examples of recorded resistance | - | |||
| Physical state | Off-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 | None | |||
| Formulation and application details | Often supplied as a wettable powder or emulsifiable concentrate. | |||
ENVIRONMENTAL FATE
for fenarimol
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 13.7 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 73300 | A5 - Ethyl acetate | - | |
| 98000 | A5 - Methanol | - | ||
| 920 | C4 - n-Heptane | - | ||
| 33300 | A5 - Xylene | - | ||
| Melting point (oC) | 118 | A5 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | 240 | A5 | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 4.90 X 1003 | Calculated | - |
| Log P | 3.69 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.4 | A5 | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 0.065 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 7.0 X 10-04 | A5 | Non-volatile | |
GUS leaching potential index  |
3.23 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 4.70 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral solution: 205.8nm = 33700; [Acidic solution: 204.8nm = 35900; [Basic solution: 221nm = 19000 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 250 | H4 | Persistent |
| DT50 (lab at 20oC) | 703 | A5 | Very persistent | |
| DT50 (field) | 74 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 436-1360 days, field studies DT50 range 14-130 days; Other sources: range 60-130 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 7.8 | R3 | - |
| Note | Grape berries, n=1 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 0.5 | A5 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Not sensitive to pH | |||
| Water-sediment DT50 (days) | Stable | A5 | - | |
| Water phase only DT50 (days) | 4 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 6.7 | A5 | Slightly mobile |
| Kfoc | 734 | |||
| 1/n | 0.87 | |||
| Notes and range | EU dossier kf range 1.5-11.9 mL/g, Kfoc range 500-942 mL/g, 1/n range 0.86-0.90 | |||
| pH sensitivity | No | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| - | fenarimol-N-oxide | Animal | - | - |
| 2-chloro-2-(5-pyrimidyl)-4-chloro-benzophenone | - | Water (Photolysis) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 113 | F4 Whole fish | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | ~ 2500 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | > 1.1 | L2 Rat, 2 year | High |
| (ppm diet) | > 25 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 6250 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 4.1 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.43 | A4 Oncorhynchus mykiss, 69 day | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 6.8 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.113 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | 1.45 | A5 Chironomus riparius | Moderate | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.625 | A5 Chironomus riparius | Moderate | |
| 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) | 1.48 | A4 Unknown species | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.1 | Q2 Unknown species | Moderate | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 10 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 250 | C4 Eisenia foetida | Moderate | |
| 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 | 100 | Mortality Dose: 32 g ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 30 | Mortality Dose: 32 g ha-1 A5 Typhlodromus pyri, protonymph |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 7 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for fenarimol
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) | ~ 2500 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rabbit | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 2.04 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.02 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.02 | A2 Rat, SF=100 | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Acceptable level of risk for bystanders | ||
| Occupational | Acceptable level of risk for operators and other workers | |||
| 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 | May be fatal May cause irritation or burns Vapour may cause dizziness or suffocation Endocrine issues - Antagonist of androgenic action |
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: 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 |
Vapour may form explosive mixture with air Highly flammable IMDG Transport Code is usually 6.1 |
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| CLP classification 2013 | Health: H361fd, H362 Environment: H411 |
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| EC Risk Classification |
Reproduction risk category 3: R62, R63, R64 N - Dangerous for the environment: R51, R53 |
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| EC Safety Classification |
S2, S36/37, S61 | |||
| WHO Classification | III | - | Slightly hazardous | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | Usually 3017 or 3077 | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | fenarimol |
| French | fenarimol |
| German | Fenarimol |
| Danish | fenarimol |
| Italian | fenarimol |
| Spanish | fenarimol |
| Greek | fenarimol |
| Slovenian | fenarimol |
| Polish | fenarimol |
| Swedish | - |
| Hungarian | fenarimol |
| Dutch | fenarimol |
Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk