Propineb (Ref: BAY 46131)

Propineb (Ref: BAY 46131)	Last updated: 12/01/2021
(Also known as: propinebe; methyl-metiram )

GENERAL INFORMATION

Description

A foliar-applied fungicide with long residual activity used on a wide range of agricultural crops

Example pests controlled

Downy mildew; Black rots; Grey moulds; Scab; Leaf spots; Blossom wilt

Example applications

Grapes; Tomatoes; Potatoes; Pome fruit; Onions; Melons; bell peppers

Efficacy & activity

Propineb has been tested in field development trials which demonstrated efficacious activity.

Availability status

Current

Introduction & key dates

1965, first introduced

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Italy/Romania

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

Chemical structure

Isomerism

A molecule with one chiral feature.

Chemical formula

C₅H₈N₂S₄Zn

Canonical SMILES

CC(CNC(=S)[S-])NC(=S)[S-].[Zn+2]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

HLQULFUYWRYRJQ-UHFFFAOYSA-M

International Chemical Identifier (InChI)

InChI=1S/C5H10N2S4.Zn/c1-3(7-5(10)11)2-6-4(8)9;/h3H,2H2,1H3,(H2,6,8,9)(H2,7,10,11);/q;+2/p-2/rC5H8N2S4Zn/c1-3-2-6-4(8)10-12-11-5(9)7-3/h3H,2H2,1H3,(H,6,8)(H,7,9)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Carbamate

Minimum active substance purity

Known relevant impurities

EU dossier: aresenic as an impurity

Substance origin

Synthetic

Mode of action

Contact action with protective properties and long residual activity. Multi-site activity.

CAS RN

12071-83-9

Alternative/old CAS RN

9016-72-2

EC number

235-134-0

CIPAC number

177

US EPA chemical code

522200

PubChem CID

6100711

Molecular mass

289.80

PIN (Preferred Identification Name)

IUPAC name

polymeric zinc propylenebis(dithiocarbamate)

CAS name

((2-((dithiocarboxy)amino)-1-methylethyl)carbamodithioato))(2-)-kS,kS')zinc

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

White powder

Related substances & organisms

cymoxanil

iprovalicarb

oxadixyl

Formulations

Property

Value

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

Melody Duo
Antracol
Aerial
Agrocol

Example products using this active

Bayer CropScience
AgroSan
FCC
Farmoplant

Formulation and application details

Available in a variety of formulations including dusts, flowables, water-dispersible granules and wettable powders.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

100

Toluene

100

Acetone

100

n-Heptane

100

Dichloromethane

Melting point (°C)

Decomposes before melting

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

150

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

5.50 X 10^-01

Calculated

Log P

-0.26

Low

Bulk density (g ml⁻¹)

1.81

Dissociation constant pKa) at 25 °C

Not applicable

Not determinable

Vapour pressure at 20 °C (mPa)

0.16

Low volatility

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

8.00 X 10^-08

for main metablite PTU

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

4.3

Non-persistent

DT₅₀ (lab at 20 °C)

4.3

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

0.4

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2015 dossier lab studies DT₅₀ range 0.5-8.1 days, Soils=2; EU 2003 dossier Lab studies DT₅₀ range 0.1-6 days, DT₉₀ range 0.12-19 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

3.0

Note

Published literature RL₅₀ range 2.3-5.3 days, 6 field crops, various matrices, n=9

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.1

Fast

Note

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

Value

1.5

Non-persistent

Note

pH sensitive: DT₅₀ 24 hours at pH 4, 53 hours at pH 9 all at 22 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

1.0

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

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

propylene urea

Soil

0.422

Major fraction, Relevant

propylene thiourea

Soil

0.313

Major fraction, Relevant

propineb-DIDT

Soil

0.256

Major fraction, Relevant

4-methyl-imidazoline hydrochloride

Soil

0.117

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

800

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5000

Coturnix japonica

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Unknown species

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.33

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.082

Oncorhynchus mykiss

Moderate

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

1.5

Daphnia magna

Moderate

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

0.015

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)

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)

0.055

Pseudokirchneriella subcapitata

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)

> 107.9

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)

> 700

Moderate

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

5.6

Mortality
Typhlodromus pyri

% Effect

Mortality [Dose: 1.3 kg ha⁻¹]
Poecilus cupreus adult

Other arthropod (2)

LR₅₀ g ha⁻¹

7000

A5 Aphidius rhopalosiphi
-

% Effect

Beneficial capacity - Full recovery after 4 weeks [Dose: Field rate]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 100.8 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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.42

Rat

Other Mammal toxicity endpoints

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

0.007

Rat SF=100

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

0.1

Rat SF=100

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

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

0.003

Rat 1 year SF=100

Dermal penetration studies (%)

0.007

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

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

Eye irritant

Phototoxicant

General human health issues

Primarily distributes via the thyroid gland, potentially thyroid toxicant
May damage lungs or cause muscular problems
USEPA - probable human carcinogen, EFSA - no carcinogenic potential

Handling issues

Property

Value and interpretation

General

Avoid generation of dust
IMDG Transport Code is usually 9
Not oxidising or explosive

CLP classification 2013

Health: H317, H332, H373
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R20, R48/22, R43
N - Dangerous for the environment: R50

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

propineb

French

propinebe

German

Propineb

Danish

propineb

Italian

propineb

Spanish

propineb

Greek

Polish

propineb

Swedish

Hungarian

propineb

Dutch

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