Propyzamide (Ref: RH 315)

Propyzamide (Ref: RH 315)	Last updated: 17/03/2024
(Also known as: pronamide)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Potential for particle bound transport: High	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate; Possible Carcinogen

GENERAL INFORMATION

Description

A residual, systemic post-emergent herbicide for use in a wide range of crops to control annual and perennial weeds

Example pests controlled

Certain grasses; broad-leaved weeds including chickweed, mayweed, poppy, black bindweed, fat hen, speedwells

Example applications

Alfalfa; OSR; Beans; Root crops; Fruit including apples, blackberry, boysenberry, blueberry, cherry, peach, pear, plum, prunes, grapes and others; Artichoke; Clover; Endive and various head lettuce; Ornamentals; Non-cropped and utility sites

Efficacy & activity

Availability status

Current

Introduction & key dates

1969, introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2025

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/UK

Date EC 1107/2009 inclusion expires

30/06/2025

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
	✓	✓	✓	✓		✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Australia

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₁₁Cl₂NO

Canonical SMILES

CC(C)(C#C)NC(=O)C1=CC(=CC(=C1)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

PHNUZKMIPFFYSO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H11Cl2NO/c1-4-12(2,3)15-11(16)8-5-9(13)7-10(14)6-8/h1,5-7H,2-3H3,(H,15,16)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
propyzamide	-

General status

Pesticide type

Herbicide

Substance groups

Amide herbicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, systemic absorbed by roots and translocated. Microtubule assembly inhibition.

CAS RN

23950-58-5

EC number

245-951-4

CIPAC number

315

US EPA chemical code

101701

PubChem CID

32154

CLP index number

616-055-00-4

Molecular mass

256.13

PIN (Preferred Identification Name)

IUPAC name

3,5-dichloro-N-(1,1-dimethylprop-2-ynyl)benzamide

CAS name

3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide

Other status information

Potential groundwater contaminant

Relevant Environmental Water Quality Standards

UK Environment Agency non-statutory standard for the protection of aquatic life in freshwater and saltwater: 100 µg l⁻¹ as annual average; 1000 µg l⁻¹ as max acceptable conc.

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Off-white powdery solid

Formulations

Property

Value

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

AgriGuard
Dow AgroSciences
Interfarm Ltd
Standon
SumiAgro
Rohm & Haas

Example products using this active

Bulwark Flo
Kerb 50W
Kerb Flo
Kerb ProFlo
Menace
Clanex
ASTROkerb

Formulation and application details

Available in a variety of formulations including granules & wettable powders

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

9.0

Low

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

139000

Acetone

63800

Methanol

501

Hexane

9670

Toluene

Melting point (°C)

156

Boiling point (°C)

283

Degradation point (°C)

281

Flashpoint (°C)

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

1.86 X 10⁰³

Calculated

Log P

3.27

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.33

Dissociation constant pKa) at 25 °C

10.38

Vapour pressure at 20 °C (mPa)

0.058

Low volatility

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

7.52 X 10^-09

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

pH7: 207nm=42200
pH 12.4: 206nm=43600
pH 0.6: 219nm=14300

Surface tension (mN m⁻¹)

71.5

at 20 °C 90%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

50.5

Moderately persistent

DT₅₀ (lab at 20 °C)

50.5

Moderately persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

233.1

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2016 dossier lab studies DT₅₀ range 13.9-271.3 days, DT₉₀ range 59.2-648.3 days, Soils=8

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

63.8

Note

Alfalfa leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Very slow, almost stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Slow

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

5.5

Slightly mobile

K_oc

840

Notes and range

EU 2003 dossier K_d range 3.2-10.0 mL g⁻¹, K_oc range 548-1340 mL g⁻¹, Soils=6

Freundlich

K_f

19.9

Slightly mobile

K_foc

1626

¹/_n

1.02

Notes and range

EU 2016 dossier K_f range 18-47 mL g⁻¹, K_foc range 703-5390 mL g⁻¹, ¹/_n range 0.96-1.08, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.34

Calculated

Low leachability

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

Value

3.21 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

9.7

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methylene-oxazoline (Ref: RH 24644)

Major fraction

0.415

N-(1,1-dimethylacetonyl)-3,5-dichlorobenzamide (Ref: RH-24580)

Major fraction

0.240

N-(1,1-dimethyl-2,3-dihydroxypropyl)-3,5-dichlorobenzamide (Ref: RH-26521)

Aerobic

3,5-dichlorobenzoic acid (Ref: RH-20839)

Aerobic

N-(1,1-dimethyl-3-hydroxacetonyl)-3,5-dichlorobenzamide (Ref: RH-26702)

Photolysis

2-(3,5-dichlorophenyl)-4,4-dimethyl-S-hydroxymethyloxazoline (Ref: RH-25891)

Anaerobic

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methylene-oxazoline (Ref: RH 24644)

Relevant

N-(1,1-dimethylacetonyl)-3,5-dichlorobenzamide (Ref: RH-24580)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

beta-(3,5-dichlorobenzamido)-beta-mebutyric acid (Ref: RH-26059)

Surface water (Photolysis)

N-(1,1-dimethyl-2,3-dihydroxypropyl)-3,5-dichlorobenzamide (Ref: RH-26521)

Surface water

3,5-dichloro-N-(1,1-dimethyl-2-propenyl)benzamide (Ref: RH-24655)

Surface water

3,5-dichlorobenzoic acid (Ref: RH-20839)

Surface water (Photolysis)

2-(3,5-dichlorophenyl)-4,4-dimethyl-S-hydroxymethyloxazoline (Ref: RH-25891)

Surface water (Photolysis)

N-(1,1-dimethyl-3-hydroxacetonyl)-3,5-dichlorobenzamide (Ref: RH-26702)

Surface water (Photolysis)

3,5-dichlorobenzamide (Ref: RH-24298)

Surface water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

> 200

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

> 97.7

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

6578

Coturnix japonica

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 10000 mg kg feed⁻¹

Colinus virginianus

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

30.9

Colinus virginianus NOEL

Moderate

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 173

Eisenia foetida

Moderate

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

3.3

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: Not stated

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

1.4

Folsomia candida corr

Non-target plants

Honeybees (Apis spp.)

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

> 136

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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

Chronic

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 2500

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 1886

Typhlodromus pyri Lifecycle

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 4.7

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.94

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

> 5.6

Daphnia magna

Moderate

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

0.6

Daphnia magna

Moderate

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

3.9

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)

0.34

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

0.45

Chironomus riparius

Moderate

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

1.4

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

2.8

Raphidocelis subcapitata

Moderate

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

> 2.1

Rat 4 hr (nose only aerosol)

Other Mammal toxicity endpoints

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

0.05

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

0.13

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

None allocated

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

0.05

Dermal penetration studies (%)

17-19

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible liver, kidney & spleen toxicant
Associated with thyroid follicular cell adenomas and Leydig cell benign tumours
CLP data - suspected carcinogen; US EPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H351
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

propyzamide

French

propyzamide

German

Propyzamid

Danish

propyzamide

Italian

propizamide

Spanish

propizamida; pronamida

Greek

propyzamide

Polish

propyzamid

Swedish

propyzamid

Hungarian

propizamid

Dutch

Norwegian

Record last updated:	17/03/2024
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