| fenbuconazole (Ref: RH 7592) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for fenbuconazole
Description: A fungicide used to control a range of diseases including powdery mildew, black rot and scab
Example pests controlled: Powdery mildew, Black rot, Scab, Rusts, Smuts, Leaf spots
Example applications: Cereals; Vines; Top fruit; Stone fruit; Bananas; Pecans; Rice
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1992, Europe
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Sovenia/UK |
| Date inclusion expires | 30/04/2021 |
| EU Candidate for substitution (CfS) | No |
| 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, Latin America, Asia, Africa
Chemical structure:
| Isomerism | A chiral molecule, fenbuconazole is a racemate of the R- and S-forms |
| Chemical formula | C19H17ClN4 |
| Canonical SMILES | C1=CC=C(C=C1)C(CCC2=CC=C(C=C2)Cl)(CN3C=NC=N3)C#N |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | RQDJADAKIFFEKQ-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C19H17ClN4/c20-18-8-6-16(7-9-18)10-11-19(12-21,13-24-15-22-14-23-24)17-4-2-1-3-5-17/h1-9,14-15H,10-11,13H2 |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Fenbuconazole | Unstated isomer |  |
General status:
| Pesticide type | Fungicide | |
| Substance group | Triazole | |
| Minimum active substance purity | 965 g/kg (50:50 racemic mixture) | |
| Known relevant impurities | EU dossier: none declared | |
| Substance origin | Synthetic | |
| Mode of action | Systemic protectant and curative, acts by inhibiting sterol biosynthesis in fungi. | |
| CAS RN | 114369-43-6 | |
| EC number | 406-140-2 | |
| CIPAC number | 694 | |
| US EPA chemical code | 129011 | |
| PubChem CID | 86138 | |
| Molecular mass (g mol-1) | 336.82 | |
| PIN (Preferred Identification Name) | rac-(2R)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butanenitrile | |
| IUPAC name | 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile | |
| CAS name | α-(2-(4-chlorophenyl)ethyl)-a-phenyl-1H-1,2,4-triazole-1-propanenitrile | |
| 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) | 3 | |
| Examples of recorded resistance | - | |
| Physical state | Colourless to off-white crystalline powder | |
| 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 oil emulsion which is mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for fenbuconazole
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 2.47 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 132000 | A5 - Ethyl acetate | - | |
| 250000 | A5 - Acetone | - | ||
| 680 | A5 - n-Heptane | - | ||
| 26000 | A5 - Xylene | - | ||
| Melting point (oC) | 126.5 | A5 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | 360 | A3 - exothermic decomposition above this temperature | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.17 X 1003 | Calculated | - |
| Log P | 3.79 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.28 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 3.4 X 10-04 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 3.01 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
0.77 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.50 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral solution 195nm = 35600; [Acidic solution 200nm = 20600; [Basic solution 217nm = 12100 | A5 | - | |
| Surface tension (mN m-1) | 69.5 | A5 at 22oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 60 | B4 | Moderately persistent |
| DT50 (lab at 20oC) | 152 | A5 | Persistent | |
| DT50 (field) | 61 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 659 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 33-590 days, DT90 range 109-1219 days, field studies DT50 range 6-98 days ; Other studies DT50 (1) lab data - no degradation after 363 days, field study range 28-84 days (B3), (2) 247 days (DW4) | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 10.2 | R4 | - |
| Note | Published literature RL50 range 5.7-14.7 days, 2 field & undercover grown fruit, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | Stable | A5 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable pH 5 to pH 9 | |||
| Water-sediment DT50 (days) | 3.4 | B2 | Fast | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 45 | A5 | Non-mobile |
| Kfoc | 4425 | |||
| 1/n | 1.00 | |||
| Notes and range | EU dossier: Kf range 5.1-115.4 mL/g, Kfoc range 2185-9043 mL/g, 1/n range 0.845-1.222, Soils=5 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 1,2,4-triazole (Ref: CGA 71019) |
Soil | 0.124 | Major fraction, Relevant | |
| cis-5-(4-chlorophenyl)-dihydro-3-phenyl-3-(1H-1,2,4-triazole-1-ylmethyl)-2-3H-furanone (Ref: RH-9129) | Soil | 0.097 | Minor fraction, Relevant | |
| 4-(4-chlorophenyl)-2-(methyl-1H-1,2,4-triazole)-4-oxo-2-phenylbutanenitrile (Ref: RH-6467) | Soil | 0.056 | Minor fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| (2RS)-4-(4-chlorophenyl)-2-(4-hydroxyphenyl)-2-(1H-1,2,4-triazol-1-hydroxyphenyl)-2-(1H-1,2,4-triazol-1- (Ref: RH 1311) |
4-phenol fenbuconazole | Animal | - | - |
| 3-(1H-1,2,4-triazol-1-yl)-DL-alanine (Ref: RH 3968) Note: Toxicologically relevant |
triazole alanine | Plant | - | - |
| 1H-1,2,4-triazol-1-ylacetic acid (Ref: RH 4098) Note: Toxicologically relevant |
TAA; Triazole acetic acid | Rat | - | - |
| (2RS)-4-(4-chloro-3-hydroxyphenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butanenitrile (Ref: RH 4911) Note: Toxicologically relevant |
hydroxy phenol fenbuconazole | Plant | - | - |
| (2RS)-4-(4-chlorophenyl)-2-(hydroxymethyl)-2-phenylbutanenitrile (Ref: RH 7968) |
- | Animal | - | - |
ECOTOXICOLOGY
for fenbuconazole
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 160 | A5 Whole fish | Threshold for concern |
| CT50 (days) | 1.4 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | > 1.4 | B5 Rat | High |
| (ppm diet) | > 20 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2150 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 1.5 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.32 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 2.3 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.078 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.75 | A5 Americamysis bahia | Moderate | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 1.73 | A5 Chironomus riparius | Moderate | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | 8.0 | A5 Chironomus riparius | Moderate | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.33 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.18 | Q2 Unknown species | Moderate | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 5.5 | A5 | Moderate |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 5.2 | A5 | 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) | > 100 | A5 Eisenia foetida, corr | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 39 | A4 Eisenia foetida, corr | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 0.0 | Mortality Dose: 0.136 kg ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 0.0 | Mortality Dose: 0.063 kg ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.49 mg kg-1, 28days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for fenbuconazole
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) | > 2000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 2.1 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.006 | A4 Dog, SF=100, Proposed | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.3 | A2 Rat, SF=100, Proposed | - | |
| 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 | A5 Rat, SF=300, Proposed | - | |
| Dermal penetration studies (%) | 4-30 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Vapour drift unlikley to be a concern to bystanders | ||
| Occupational | Acceptable risk for registered applications - PPE/PPC advised | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | 0.1 | EU Dir 89/778/EC limit; Calc MAC=18.0 μg l-1; A5 | - | |
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 | Possible liver & kidney toxicant USEPA - possible human carcinogen Endocrine issues - Inhibition of thyroid hormones production |
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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 |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Environment: H400, H410 | |||
| EC Risk Classification |
Xn - Harmful: R63 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S60, S61 | |||
| WHO Classification | III | - | Slightly hazardous | |
| US EPA Classification (formulation) | II | - | Warning - Moderately toxic | |
| UN Number | Usually 1993 or 3077 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for fenbuconazole
| Language | Name |
| English | fenbuconazole |
| French | fenbuconazole |
| German | Fenbuconazol |
| Danish | fenbuconazol |
| Italian | fenbuconazolo |
| Spanish | fenbuconazol |
| Greek | - |
| Slovenian | fenbukonazol |
| Polish | fenbukonazol |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk