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(R)-hexaconazole
Last updated: 01/06/2018
(Also known as: (-) hexaconazole)

GENERAL INFORMATION
Description
An isomer of the conazole (imidazole) fungicide used to control both seed-borne and soil-borne diseases especially Ascomycetes and Basidiomycetes spp.
Example pests controlled
Powdery mildew, Scabs, Rusts
Example applications
Vines; Apples; Pears,; Bananas; Vegetables; Some small grain cereals
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1986
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Italy
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
Yes as hexaconazole
Approved for use (✓) under EC 1107/2009 in the following EU Member States
ATAustria
BEBelgium
BGBulgaria
CYCyprus
CZCzech Republic
DEGermany
DKDenmark
EEEstonia
ELGreece
                 
ESSpain
FIFinland
FRFrance
HRCroatia
HUHungary
IEIreland
ITItaly
LTLithuania
LULuxembourg
                 
LVLatvia
MTMalta
NLNetherlands
PLPoland
PTPortugal
RORomania
SESweden
SISlovenia
SKSlovakia
                 
Also used in
Also used in
Australia
Chemical structure
Isomerism
(R)-hexaconazole is the R-isomer of chiral hexaconazole
Chemical formula
C₁₄H₁₇Cl₂N₃O
Canonical SMILES
CCCCC(CN1C=NC=N1)(C2=C(C=C(C=C2)Cl)Cl)O
Isomeric SMILES
CCCC[C@](CN1C=NC=N1)(C2=C(C=C(C=C2)Cl)Cl)O
International Chemical Identifier key (InChIKey)
STMIIPIFODONDC-AWEZNQCLSA-N
International Chemical Identifier (InChI)
InChI=1S/C14H17Cl2N3O/c1-2-3-6-14(20,8-19-10-17-9-18-19)12-5-4-11(15)7-13(12)16/h4-5,7,9-10,20H,2-3,6,8H2,1H3/t14-/m0/s1
2D structure diagram/image available?
No
General status
Pesticide type
Fungicide, Other substance
Other constituent type
Wood preservative
Substance group
Triazole
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Broad spectrum, systemic with protective and curative action. Disrupts membrane function. Sterol biosynthesis inhibitor.
CAS RN
-
EC number
-
CIPAC number
465
US EPA chemical code
128925
PubChem CID
37888330
Molecular mass
314.21
PIN (Preferred Identification Name)
-
IUPAC name
(R)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol
CAS name
α-butyl-α-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanol
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
White crystalline solid
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Passport
  • Manage
  • Anvil
  • Planete Aster
Example products using this active
  • AgroCare
  • FCC
  • Syngenta
Formulation and application details
Available in a variety of formulations including oil miscible liquids, soluble grains and suspension concentrates.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
- - -
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
- - -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
- - -
Log P
- - -
Bulk density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
- - -
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
3.9
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature data range 2.8-5.5 days, 4 field & glasshouse crops, various matrices, n=4
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
- - -
Koc
-
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated - -
Note
-
Potential for particle bound transport index
- - -
Potential for loss via drain flow
- - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
2189
P3 P = Other governments and regulators
3 = Unverified data of known source
Rat as the isomer mix
Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 4000
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Anas platyrhynchos as the isomer mix
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
3.4
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss as the isomer mix
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 2.9
P3 P = Other governments and regulators
3 = Unverified data of known source
Daphnia magna as the isomer mix
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)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
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)
- - -
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)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
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
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
2189
P3 P = Other governments and regulators
3 = Unverified data of known source
Rat as the isomer mix
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat as the isomer mix
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
?Possibly, status not identified
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
Yes, known to cause a problem
Yes, known to cause a problem
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
USEPA - possible human carcinogen
Endocrine issues - Inhibition of aromatase activity, decrease of the estrogens production
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H302, H317
Environment: H411
EC Risk Classification
Xn - Harmful: R22, R43
N - Dangerous for the environment: R51, R53
EC Safety Classification
S2, S24, S37, S61
WHO Classification
III (Slightly hazardous)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
(R)-hexaconazole
French
(R)-hexaconazole
German
(R)-Hexaconazol
Danish
(R)-hexaconazol
Italian
(R)-esaconozolo
Spanish
(R)-hexaconazol
Greek
-
Polish
(R)-heksakonazol
Swedish
-
Hungarian
(R)-hexakonazol
Dutch
-

Record last updated: 01/06/2018
Contact: aeru@herts.ac.uk
Please cite as: Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242