difenoconazole (Ref: CGA 169374) ** Translations

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

GENERAL INFORMATION

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

Introduction: 1988 first reported; 1989, introduced France

EC Directive 1107/2009 (repealing 91/414):

Status	Annex 1
Dossier rapporteur/co-rapporteur	Sweden
Date inclusion expires	31/12/2018

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:

Pesticide type	Fungicide
Substance group	Triazole
Substance origin	Synthetic
Mode of action	Systemic with preventative and curative action. Disrupts membrane function.
CAS RN	119446-68-3
EC number	-
CIPAC number	687
US EPA chemical code	-
Chiral molecule	Yes
Chemical formula	C19H17Cl2N3O3
SMILES	O1C[C@@H](C)O[C@@]1(Cn1ncnc1)c1c(Cl)cc(Oc2ccc(Cl)cc2)cc1
International Chemical Identifier (InChI)	InChI=1/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
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	406.26
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	-
Herbicide Resistance Classification (HRAC)	Not applicable
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	3
Physical state	White crystals
Related substances & organisms	azoxystrobin fenpropidin

Formulations:

Property	Value
Example manufacturers of products using this active	Nufarm Syngenta
Example products using this active	Amistar Top Plover Spyrale Difcor 250 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

Property		Value	Source/Quality Score/Other Information	Interpretation
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 25oC (mPa)		3.33 X 10-05	A5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		9.0 X 10-07	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		7.31 X 10-10	K3	Non-volatile
GUS leaching potential 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	Value	1.79 X 10-02	Calculated	-
	Note	-
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	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
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	-
	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)
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	Stable
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	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		Value	Source/Quality Score/Other Information	Interpretation
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	91/414 Relevancy
1-[2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-1H-[1,2,4]triazol-yl]-ethanol (Ref: CGA 205375)		Soil	0.119	Minor fraction, Relevant
1,2,4-triazole (Ref: CGA 71019)		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

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	330	A5	Threshold for concern
	CT50 (days)	1.0		-
Bioaccumulation potential		-	Calculated	Moderate
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	-
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	-
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)		-	-	-
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 - Acute 48 hour LD50 (µg bee-1)		> 100	A5 Contact	Moderate
Earthworms - Acute 14 day LC50 (mg kg-1)		> 610	A5	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	178	48 hour A5 Aphidius rhopalosiphi, adult	Moderately harmful at 1 kg ha-1
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	112	7 day A5 Typhlodromus pyri	Moderately harmful at 1 kg ha-1
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: Unclear results Carbon mineralisation: No significant effect	A5 Dose: 16.7 mg/kg, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
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, 4hr (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	-
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 Limits		-	-	-
Exposure Routes	Public	No unacceptable risks to bystanders identified Acceptable safety margin in place for consumers
	Occupational	No unacceptable risks to workers identified
Examples of European MRLs (mg kg-1)	Value	Cereal grains: 0.02; Root vegetables: 0.2; Pome fruit: 0.3
	Note	A5 EU dossier proposals For the EU pesticides database click here
Drinking Water MAC (µg l-1)		0.1	A5	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-	-
General human health issues		Liver, heart , thyroid and kidney toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising IMDG Transport Code is usually 9
CLP classification 2013		-
EC Risk Classification		Xn - Harmful: R22 N - Dangerous for the environment: R50, R53
EC Safety Classification		S46, S60, S61
WHO Classification		II	-	Moderately hazardous
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		Usually 3082
Waste disposal & packaging		Usually Packaging Group III (minor danger)

TRANSLATIONS