Procymidone (Ref: S 7131)

Procymidone (Ref: S 7131)	Last updated: 29/06/2019
(Not known by any other names)

GENERAL INFORMATION

Description

A fungicide widely used in horticulture as a seed dressing, pre-harvest spray or post-harvest dip for the control of various fungal diseases

Example pests controlled

Grey mould; Neck rot; Brown rot; Blosson blight; Twig wilt

Example applications

Vegetables including onions; Fruit including peaches, plums and cherries; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1976, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

France

Date EC 1107/2009 inclusion expires

Expired

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

A molecule with two chiral features.

Chemical formula

C₁₃H₁₁Cl₂NO₂

Canonical SMILES

CC12CC1(C(=O)N(C2=O)C3=CC(=CC(=C3)Cl)Cl)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

QXJKBPAVAHBARF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H11Cl2NO2/c1-12-6-13(12,2)11(18)16(10(12)17)9-4-7(14)3-8(15)5-9/h3-5H,6H2,1-2H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
procymidone	Unstated isomer

General status

Pesticide type

Fungicide

Substance group

Dicarboximide

Minimum active substance purity

985 g/Kg

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with protective and curative properties. Osmotic signal transduction.

CAS RN

32809-16-8

EC number

251-233-1

CIPAC number

383

US EPA chemical code

129044

PubChem CID

36242

Molecular mass

284.14

PIN (Preferred Identification Name)

IUPAC name

N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide

CAS name

3-(3,5-dichlorophenyl)-1,5-dimethyl-3-azabicyclo(3.1.0)hexane-2,4-dione

Other status information

Chemical subject to PIC regulations

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

White granular powder

Formulations

Property

Value

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

Sumisclex

Example products using this active

Sumitomo
SOPRA

Formulation and application details

Usually supplied as a wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.46

Low

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

180000

Acetone

66000

Toluene

16000

Methanol

148000

Cyclohexanone

Melting point (°C)

164.5

Boiling point (°C)

478

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰³

Calculated

Log P

3.3

High

Bulk density (g ml⁻¹)

1.43

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.023

Low volatility

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

2.65 X 10^-03

Non-volatile

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

Neutral solution: 210nm = 37390
Acidic solution: 210nm = 37641
Basic solution: 220nm = 29100, 251nm = 14800

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

784.5

Very persistent

DT₅₀ (field)

208.3

Persistent

DT₉₀ (lab at 20 °C)

872

Very persistent

DT₉₀ (field)

349

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 48-189 days (neutral/alkaline soils), 520-2381 days (acid soils), DT₉₀ range 675-1068 days, field studies DT₅₀ range 17-158 days (neutral/alkaline soisl), 161-497 days (acid soils), DT₉₀ range 56-525 days

Dissipation rate RL₅₀ on plant matrix

Value

6.6

Note

Published literature RL₅₀ range 2.1-11.1 days, 2 undercover crops, various matrices, n=2

Dissipation rate RL₅₀ on and in plant matrix

Value

11.8

Note

Published literature RL₅₀ range 5.0-10.9 days, 4 field & undercover grown crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Not a major degardation route

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

Value

24.7

Non-persistent

Note

pH and temperature sensitive: DT₅₀ 93 days at pH 4 and 25 °C, 135 days at pH 4 and 20 °C, 62 days at pH 5 and 30 °C, 17 days at pH 7 and 25 °C, 0.06 days at pH 9 and 25 °C, 0.09 days at pH 9 and 20 °C

Water-sediment DT₅₀ (days)

1.4

Fast

Water phase only DT₅₀ (days)

0.8

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

378

Notes and range

EU dossier K_oc range 199-513 mL g⁻¹; Other sources: 1500 mL g⁻¹ (DW3)

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

None, correlation with OC noted.

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.30

Calculated

High leachability

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

Value

5.06 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-(3,5-dichlorophenyl-carbamoyl)-1,2-dimethyl(cyclopropanecarboxylic acid)

Soil

0.281

Major fraction, Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3,5-dichloroanaline
Note: Rat LD50 oral = 820 mg/kg bw

3,5-DCA

Rat

CCA

Water (Hydrolysis)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

46.95

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

> 1000

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 4092

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5200 mg kg feed⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

7.22

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.48

Oncorhynchus mykiss

Moderate

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

> 1.8

Daphnia magna

Moderate

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

0.99

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)

0.12

Chironomus riparius

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)

2.6

Scenedesmus acutus

Moderate

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)

> 100

Low

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

> 100

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)

> 1000

Eisenia foetida

Low

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

29.7 / -7.0

Mortality / Fecundity [Dose: 0.15 kg ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

10.5 / 16.0

Mortality / Reproduction [Dose: 0.664 kg ha⁻¹]
Chrysoperla carnea

Soil micro-organisms

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

Dose: 20 mg product/kg soil

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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.5

Rat

Other Mammal toxicity endpoints

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

0.0028

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

0.012

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

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

0.012

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver and testes toxicant, androgen; USEPA - probable human carcinogen
Endocrine issues - Competitive binding to androgen receptor

Handling issues

Property

Value and interpretation

General

Not explosive

CLP classification 2013

Health: H332
Environment: H413

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 2: R61
N - Dangerous for the environment: R51, R53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

procymidone

French

procymidone

German

Procymidone

Danish

procymidon

Italian

procimidone

Spanish

procimidona

Greek

Polish

procymidon

Swedish

Hungarian

procimidon

Dutch

Record last updated:	29/06/2019
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