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difenoconazole (Ref: CGA 169374)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

SUMMARY

Difenoconazole is a fungicide used for disease control in many fruits, vegetables, cereals and other field crops. Although potentially a mobile molecule it is unlikely to leach due to its low aqueous solubility. It does however have potential for particle bound transport. It is slightly volatile, persistent in soil and in the aquatic environment. There are some concerns regarding its potential for bioaccumulation. Moderately toxic to humans, mammals, birds and most aquatic organisms.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for difenoconazole

Description: A broad spectrum fungicide with novel broad-range activity used as a spray or seed treatment

Example pests controlled: Leafspot; Ring spot; Early blight; Barley stripe; Covered smut; Damping-off; Seed rots

Example applications: Vegetables including carrots, asparagus, brassicas; Potatoes; Cereals including barley, oats, rye, wheat, triticale; Sweetcorn; Cotton; Canola

Efficacy & activity: Wheat/Mildew=Low; Wheat/Septoria tritici=Low; Wheat/Yellow rust=Low; Wheat/brown rust=Moderate

Availability status: Current

Introduction & key dates: 1988 first reported; 1989, introduced France

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Sweden
Date inclusion expires 31/12/2019
EU Candidate for substitution (CfS) Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule
Chemical formula C19H17Cl2N3O3
Canonical SMILES CC1COC(O1)(CN2C=NC=N2)C3=C(C=C(C=C3)OC4=CC=C(C=C4)Cl)Cl
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) BQYJATMQXGBDHF-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C19H17Cl2N3O3/c1-13-9-25-19(27-13,10-24-12-22-11-23-24)17-7-6-16(8-18(17)21)26-15-4-2-14(20)3-5-15/h2-8,11-13H,9-10H2,1H3
2D structure diagram/image available? Yes

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Difenoconazole Cis/trans isomer Click here for the CCDC structure diagram
Difenoconazole Unstated isomer Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Triazole
Minimum active substance purity 940 g/kg
Known relevant impurities EU dossier: Toluene < 5g/kg
Substance origin Synthetic
Mode of action Systemic with preventative and curative action. Disrupts membrane function - inhibition of demethylation during ergosterol synthesis.
CAS RN 119446-68-3
EC number -
CIPAC number 687
US EPA chemical code 128847
PubChem CID 86173
Molecular mass (g mol-1) 406.26
PIN (Preferred Identification Name) 1-((2-((2E,4E)-2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole
IUPAC name 3-chloro-4-((2RS,4RS;2RS,4SR)-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl)phenyl 4-chlorophenyl ether
CAS name 1-(2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazole
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 crystals
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Nufarm
  • Syngenta
Example products using this active
  • Amistar Top
  • Plover
  • Spyrale
  • Difcor 250 EC
  • Score EC
UK LERAP status None
Formulation and application details Often supplied as an emulsifiable concentrate which is mixed with water and applied as a spray or as a flowable concentrate for seed treatments.


ENVIRONMENTAL FATE

for difenoconazole

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 15.0 A4 Low
Solubility - In organic solvents at 20oC (mg l-1) 330000 L3 - Ethanol -
610000 L4 - Acetone -
500000 A3 - Toluene -
3400 L3 - n-Hexane -
Melting point (oC) 82.5 A5 -
Boiling point (oC) 101 A5 -
Degradation point (oC) 337 A5 -
Flashpoint (oC) 285 L3 -
Octanol-water partition coefficient at pH 7, 20oC P 2.29 X 1004 Calculated -
Log P 4.36 A5 High
Bulk density (g ml-1)/Specific gravity 1.37 B5 -
Dissociation constant (pKa) at 25oC 1.07 A5 -
Note: Strong acid
Vapour pressure at 20oC (mPa) 3.33 X 10-05 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 9.0 X 10-07 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 0.90 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 1.79 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 Acid: 215nm = 29306, 235nm = 17556, 275nm = 1743; [Neutral: 215nm = 28658, 235nm = 17392, 275nm = 1680; [Alkaline: 220nm = 21210, 235nm = 17176, 275nm = 1542 A5 -
Surface tension (mN m-1) 62.8 A57.0 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 130 A5 Persistent
DT50 (lab at 20oC) 130 A5 Persistent
DT50 (field) 85 A5 Moderately persistent
DT90 (lab at 20oC) 409 A5 -
DT90 (field) 277 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 53-456, DT90 range 175-1000 days, n=10; field studies DT50 range 20-265 days, DT90 range 68-879 days; Other sources: DT50 49 days (DW4)
Dissipation rate RL50 on plant matrix Value 7.4 R3 -
Note Pomegranite fruit, n=1
Dissipation rate RL50 on and in plant matrix Value 8.6 R4 -
Note Published literature RL50 range 1.1-31.9 days,14 field & undercover grown crops, various matrices, n=23
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) 1053 B5 Stable
Water phase only DT50 (days) 3 K4 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 41.0 A5 Slightly mobile
Kfoc 3760
1/n 0.87
Notes and range EU dossier Kf range 2.1-97.8, Kfoc range 400-7730 mL/g, 1/n range 0.74-0.94, Soils=8
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
1-(2-(2-chloro-4-(4-chloro-phenoxy)-phenyl)-2-1H-(1,2,4)triazol-yl)-ethanol (Ref: CGA 205375) This metabolite may cause environmental pollution, click here for further information Soil   0.119   Minor fraction, Relevant
1,2,4-triazole (Ref: CGA 71019) This metabolite may cause environmental pollution, click here for further information Soil   0.23   Major fraction, Relevancy unknown

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
Phenobarbitone - Mouse (liver) - -
2-amino-3-[1,2,4] triazol-1-yl-propionic acid
(Ref: CGA 131013)
triazole alanine; (TA) Animal; Plant - -
[1,2,4]triazol-1-yl-acetic acid
(Ref: CGA 142586)
triazole acetic acid; (TAA) Animal - -
2-chloro-4-(4-chloro-phenoxy)-benzoic acid
(Ref: CGA 189138)
difenoconazole-benzoic acid Plant - -
[1,2,4]triazol-1-yl-lactic acid
(Ref: CGA 205369)
Triazole lactic acid; (TLA) Animal - -
1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-yl-ethanone
(Ref: CGA 205374)
Note: Mice acute oral LD50 >5000 mg kg-1 bw,
difenoconazole-ketone Plant - -


ECOTOXICOLOGY

for difenoconazole

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 330 A5 Threshold for concern
CT50 (days) 1.0 -
Mammals - Acute oral LD50 (mg kg-1) 1453 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) 20 B5 Rat High
(ppm diet) 40 -
Birds - Acute LD50 (mg kg-1) > 2150 A5 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) > 5000 ppm A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 1.1 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.023 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.77 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.0056 A5 Daphnia magna High
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.15 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) 0.015 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) 10.0 A5 Chironomus riparius Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Non-target plants > 10 A5 Avena sativa, Brassica napus, Glycine maxima
Vegetative vigour, ER50
as g/ha
-
> 10 A5 Avena sativa, Brassica napus, Glycine maxima
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.032 A5 Scenedemus subspicatus Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.87 Q2 Unknown species Moderate
Honeybees (Apis spp.) Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 100 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 177 A5 Low
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) > 610 A5 Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 0.2 A3 Eisenia foetida, as product Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 178 48 hour
A5 Aphidius rhopalosiphi, adult
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 112 7 day
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: Unclear results
Carbon mineralisation: No significant adverse effect
A5
Dose: 16.7 mg kg-1, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for difenoconazole

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) 1453 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2010 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 3.3 A5 Rat, 4 hr (nose only) -
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) 0.16 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) 0.16 A5 Rat, SF=100 -
Dermal penetration studies (%) 2-4 A3 -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Acceptable safety margin in place for consumers
Occupational No unacceptable risks to workers identified
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 A5 -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A2; B3; C3; D0; E0

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Liver, heart, thyroid and kidney toxicant
USEPA - possible human carcinogen
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
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H302, H304, H315, H318, H336, H373
Environment: H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S46, S60, S61
WHO Classification II - Moderately hazardous
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for difenoconazole

Language Name
English difenoconazole
French difenoconazole
German Difenoconazol
Danish difenoconazol
Italian difenoconazolo
Spanish difenoconazol
Greek -
Slovenian difenokonazol
Polish difenokonazol
Swedish difenokonazol
Hungarian difenoconazole
Dutch difenoconazool

Record last updated: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk