Pencycuron (Ref: NTN 19701)

Pencycuron (Ref: NTN 19701)	Last updated: 12/01/2021
(Not known by any other names)

SUMMARY

Pencycuron is a phenylurea fungicide approved for use in the EU. It is virtually insoluble in water but will dissolve in most common organic solvents. It is volatile and not expected to leach to groundwater. It is moderately persistent in soils and slightly more so in water systems. It is not highly toxic to mammals but is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.

GENERAL INFORMATION

Description

A fungicide used to control diseases caused by Rhizoctonia solani and Pellicularia spp.

Example pests controlled

Black scurf; Sheath blight; Rot; Damping-off

Example applications

Potatoes; Sugarbeet; Rice; Cotton; Ornamentals; Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

1984

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Latvia/Poland

Date EC 1107/2009 inclusion expires

31/05/2021

EU Candidate for substitution (CfS)

Listed in EU database

Yes

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

Australia

Chemical structure

Isomerism

Chemical formula

C₁₉H₂₁ClN₂O

Canonical SMILES

C1CCC(C1)N(CC2=CC=C(C=C2)Cl)C(=O)NC3=CC=CC=C3

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OGYFATSSENRIKG-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H21ClN2O/c20-16-12-10-15(11-13-16)14-22(18-8-4-5-9-18)19(23)21-17-6-2-1-3-7-17/h1-3,6-7,10-13,18H,4-5,8-9,14H2,(H,21,23)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
pencycuron	-

General status

Pesticide type

Fungicide

Substance group

Phenylurea

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Non-systemic with protective action. Inhibition of mitosis and cell division.

CAS RN

66063-05-6

EC number

266-096-3

CIPAC number

402

US EPA chemical code

128823

PubChem CID

91692

Molecular mass

328.84

PIN (Preferred Identification Name)

IUPAC name

1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea

CAS name

N-((4-chlorophenyl)methyl)-N-cyclopentyl-N'-phenylurea

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)

Examples of recorded resistance

Physical state

Colourless crystals

Related substances & organisms

kaolin

talc

imazalil

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Monceren DS
Monceren IM
Pency Flowable

Example products using this active

AgriGuard
Bayer CropScience
Standon

Formulation and application details

Often supplied as a dry powder for seed treatment or as water-dispersible powders

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.3

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

230

n-Heptane

11500

Xylene

89400

Acetone

43800

Ethyl acetate

Melting point (°C)

132

Boiling point (°C)

286

Degradation point (°C)

140

decomposition begins

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

4.79 X 10⁰⁴

Calculated

Log P

4.68

High

Bulk density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.1 X 10^-04

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

5.10 X 10^-04

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Maxima at 240nm = 19720, 291nm = 10

Surface tension (mN m⁻¹)

72.1

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

82.4

Moderately persistent

DT₅₀ (lab at 20 °C)

82.4

Moderately persistent

DT₅₀ (field)

37.8

Moderately persistent

DT₉₀ (lab at 20 °C)

320.9

Persistent

DT₉₀ (field)

193.2

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 43.7-175 days (normalised), DT₉₀ range 159-625 days (normalised); field studies DT₅₀ range 31.7-68.2 days, DT₉₀ range 98-373 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.2

Note

Rice straw, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

156

Persistent

Note

pH and temperature sensitive: DT₅₀ 4.7 days at pH 5, 14.2 days at pH 7, 15 days at pH 9, all at 50 °C; extrapolated to 156 days for pH 7 at 25 °C

Water-sediment DT₅₀ (days)

113.5

Slow

Water phase only DT₅₀ (days)

5.3

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

46.0

Non-mobile

K_foc

4906

¹/_n

1.11

Notes and range

EU dossier K_f range 28.4-56.7 mL g⁻¹, K_foc range 2414-10441 mL g⁻¹, ¹/_n range 0.906-1.206, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.49

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

9.89 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

N-((4-chlorophenyl)-methyl)-N-cyclopentylamide

Soil

0.184

Major fraction, Relevant

1-cyclopentyl-3-phenylurea

Soil

0.066

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

N-(4-chlorobenzyl)-N-cyclopentylamine (Ref: THS 3995)

PB-amine; pencycuron metabolite M16

Soil; Rat (Faeces, Bile, Liver); Plant; Water/sediment

4-chloro-hippuric acid

Rat (Urinary)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

226

Threshold for concern

CT₅₀ (days)

90% in 3days

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

> 50

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

> 1000

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1750 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

122.1

Coturnix japonica NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.3

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

>= 0.3

Oncorhynchus mykiss

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 0.3

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.05

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)

0.3

Chironomus riparius emergence

Moderate

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)

> 0.3

Scenedemus subspicatus

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

0.1

Unknown species

Moderate

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 98.5

Apis mellifera

Moderate

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)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

3.3

Eisenia foetida 56 days

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

60.0

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

6200

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

685

Aphidius rhopalosiphi

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 3.44 kg ha⁻¹

Mesocosm study data

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)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.13

Rat 4 hr

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.2

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.15

Rat SF=100

Dermal penetration studies (%)

0.2-12.5

concentration dependent

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

None allocated at this time

EC Safety Classification

S21

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

pencycuron

French

pencycuron

German

Pencycuron

Danish

pencycuron

Italian

pencicuron

Spanish

pencicuron

Greek

Polish

pencykuron

Swedish

pencykuron

Hungarian

pencycuron

Dutch

pencycuron

Record last updated:	12/01/2021
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