pyrimethanil (Ref: SN 100309) ** ZK 100309 ** Translations

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GENERAL INFORMATION
for pyrimethanil

Description: A fungicide used to control fungal pathogens on fruit, vegetables and ornamentals

Example pests controlled: Grey mould; Powdery mildew; Scab; Downym mildew; Phomopis leaf spot

Example applications: Almonds; Pistachios; Fruit including grapes, stone fruits (except cherries), pome fruits, strawberries; Potatoes and other tuberous and corm vegetables; Tomatoes.; ornamentals

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1998, USA

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

Status	Approved
Dossier rapporteur/co-rapporteur	Czech Republic/Austria
Date inclusion expires	30/04/2019
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

Chemical structure:

Isomerism	-
Chemical formula	C12H13N3
Canonical SMILES	CC1=CC(=NC(=N1)NC2=CC=CC=C2)C
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	ZLIBICFPKPWGIZ-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams:

Common Name	Relationship	Link
Pyrimethanil	-

General status:

Pesticide type	Fungicide
Substance group	Anilinopyrimidine
Minimum active substance purity	975 g/kg
Known relevant impurities	EU dossier - cyanamide <0.5g/kg
Substance origin	Synthetic
Mode of action	Protective action with some curative properties. Inhibits methionine protein synthesis.
CAS RN	53112-28-0
EC number	414-220-3
CIPAC number	714
US EPA chemical code	288201
PubChem CID	91650
Molecular mass (g mol-1)	199.11
PIN (Preferred Identification Name)	-
IUPAC name	N-(4,6-dimethylpyrimidin-2-yl)aniline
CAS name	4,6-dimethyl-N-phenyl-2-pyrimidinamine
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)	9
Examples of recorded resistance	-
Physical state	Colourless crystals
Related substances & organisms	propylene glycol chlorothalonil

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	BASF
Example products using this active	Scala Walabi Botrynil
UK LERAP status	Buffer probably required in UK - see product label
Formulation and application details	Often supplied as a soluble concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE
for pyrimethanil

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		121	A5	Moderate
Solubility - In organic solvents at 20oC (mg l-1)		23700	A5 - n-Hexane	-
		412300	A5 - Toluene	-
		388800	A5 - Acetone	-
		616900	A5 - Ethyl acetate	-
Melting point (oC)		96.3	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		189.9	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	6.92 X 1002	Calculated	-
	Log P	2.84	A5	Moderate
Bulk density (g ml-1)/Specific gravity		1.19	A5	-
Dissociation constant (pKa) at 25oC		3.52	A5	-
		Note: Weak base
Vapour pressure at 20oC (mPa)		1.1	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		3.60 X 10-03	B5	Non-volatile
GUS leaching potential index		2.65	Calculated	Transition state
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.90 X 10-01	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 205nm = 16280, 211nm = 13450, 229nm = 4870, 271nm = 27200; [Acidic solution: 205nm = 16450, 245nm = 12260, 260nm = 14620, 317nm = 5300	A5	-
Surface tension (mN m-1)		61.51	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	55	A5	Moderately persistent
	DT50 (lab at 20oC)	55	A5	Moderately persistent
	DT50 (field)	29.5	A5	Non-persistent
	DT90 (lab at 20oC)	174.5	A5	-
	DT90 (field)	114	A5	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier lab studies DT50 range 27.9-71.8 days, DT90 range 93-238 days; field studies DT50 range 23-54 days, DT90 range 82-180 days
Dissipation rate RL50 on plant matrix	Value	6.1	R4	-
	Note	Published literature RL50 range 2.7-12.0 days, 2 field & undercover grown crops, various matrices, n=4
Dissipation rate RL50 on and in plant matrix	Value	15.1	R4	-
	Note	Published literature RL50 range 3.0-57.0 days, 5 field & undercover grown crops, various matrices, n=12
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	-
	Note	Not significant degradation route
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5 to pH 9 at 22 degC
Water-sediment DT50 (days)		80	A5	Moderately fast
Water phase only DT50 (days)		16.5	A5	Slow

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	3.97	A5	Moderately mobile
	Kfoc	301
	1/n	0.868
	Notes and range	EU dossier kf range 2.51-7.83, Kfoc range 75-500 mL/g, 1/n range 0.85-0.9, Soils=5
pH sensitivity		Slight tendency of increasing adsorption with decreasing pH

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
2-amino-4,6-dimethylpyrimidine (Ref: AE-F1312593)		Soil	0.115	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
(2-(4-hydroxyanilino)-4,6-dimethylpyrimidine	-	Animal	-	-
2-anilino-4,6-dimethylpyrimidin-5-ol	-	Animal	-	-
2-amino-4,6-dimethyl-pyrimidine	-	Soil	-	-

ECOTOXICOLOGY
for pyrimethanil

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	Low risk	A5 Based on LogP < 3	Low potential
	CT50 (days)	-		-
Mammals - Acute oral LD50 (mg kg-1)		4150	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	> 139	B5 Rat	Moderate
	(ppm diet)	> 900		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Anas platyrhynchos	Low
Birds - Short term dietary (LC50/LD50)		> 5200 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		10.56	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		1.6	F4 Oncorhynchus mykiss, LOEC	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		2.9	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.94	A5 Daphnia magna	Moderate
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)		4.0	A5 Chironomus riparius	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		7.8	F4 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		1.2	A5 Raphidocelis subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		313	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		4.12	A5 Eisenia foetida, corr	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	63 18	Mortality Fecundity Dose: 1 kg ha-1 A5 Aphidius rhopalosiphi, adult	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	38 52	Mortality Fecundity Dose: 1.04 kg ha-1 A5 Typhlodromus pyri	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect [Dose: 1.08 mg kg-1 soil] Carbon mineralisation: No significant adverse effect [Dose: 10.8 mg kg-1 soil]	A5	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for pyrimethanil

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)		4150	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 5000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 1.98	A5 Rat (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.17	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.12	A5 Rat, SF=100	-
Dermal penetration studies (%)		1.0-20.0	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks to bystanders identified
	Occupational	No unacceptable risks to operators or other workers identified
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
-		-		-
General human health issues		Possible liver, kidney, adrenals, bladder and thyroid toxicant USEPA - possible human carcinogen

: 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
CLP classification 2013		Environment: H411
EC Risk Classification		N - Dangerous for the environment: R51, R53
EC Safety Classification		-
WHO Classification		III	-	Slightly hazardous
US EPA Classification (formulation)		IV	-	Caution - Not acutely toxic
UN Number		3082
Waste disposal & packaging		-

TRANSLATIONS
for pyrimethanil

Language	Name
English	pyrimethanil
French	pyrimethanil
German	Pyrimethanil
Danish	pyrimethanil
Italian	pirimetanil
Spanish	pirimetanil
Greek	-
Slovenian	pirimetanil
Polish	pyrimetanil
Swedish	pyrimetanil
Hungarian	pirimetanil
Dutch	pyrimethanil

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Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk