fenbuconazole (Ref: RH 7592) |
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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 |
Also used in: Australia, USA, Latin America, Asia, Africa
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 | ![]() |
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:
ENVIRONMENTAL FATE
for fenbuconazole
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
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 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 | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
A3; B3; C3; D0; E0 | ||||||||
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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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![]() ![]() ![]() - : No data found |
Handling issues:
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: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk