Zoxamide (Ref: RH 7281)

Zoxamide (Ref: RH 7281)	Last updated: 22/08/2024
(Also known as: benzamide; RH 117281; zoxium; HSDB 7278)

SUMMARY

Zoxamide is a common broad-spectrum fungicide. It has a low aqueous solubility, is volatile and has a low potential for leaching to groundwater. It is not usually persistent in soil or water systems. Zoxamide has a low mammalian toxicity but is a probable skin sensitiser and a recognised eye irritant. It is moderately toxic to most fauna and flora.

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 Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish chronic ecotoxicity: High	Human health Low alert

GENERAL INFORMATION

Description

A fungicide used for the control of various fungal inflections including blight in potatoes and tomatoes

Example pests controlled

Early and late blight; Leaf blight; Anthracnose; Downy mildew; Bunch rot; Dead arm

Example applications

Potatoes; Grapes; Tomatoes; Curcubits including gourd, melons, squash; Onions and garlic

Efficacy & activity

Efficacy demonstrated via field trials and extensive use.

Availability status

Current

Introduction & key dates

2001, registered Europe

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2033

GB LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Latvia/France

Date EC 1107/2009 inclusion expires

30/06/2033

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

USA, Morocco

Chemical structure

Isomerism

Substance is racemic.

Chemical formula

C₁₄H₁₆Cl₃NO₂

Canonical SMILES

CCC(C)(C(=O)CCl)NC(=O)C1=CC(=C(C(=C1)Cl)C)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

SOUGWDPPRBKJEX-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H16Cl3NO2/c1-4-14(3,12(19)7-15)18-13(20)9-5-10(16)8(2)11(17)6-9/h5-6H,4,7H2,1-3H3,(H,18,20)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
zoxamide	Unstated isomer

General status

Pesticide type

Fungicide

Substance groups

Benzamide fungicide

Minimum active substance purity

953 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Contact with additional vapour activity. Rainfast preventative action with residual properties. Inhibition of mitosis and cell division (Beta-tubulin assembly in mitosis).

CAS RN

156052-68-5

EC number

605-037-1

CIPAC number

640

US EPA chemical code

101702

PubChem CID

122087

CLP index number

616-141-00-1

Molecular mass

336.64

PIN (Preferred Identification Name)

rac-3,5-dichloro-N-[(3R)-1-chloro-3-methyl-2-oxopentan-3-yl]-4-methylbenzamide

IUPAC name

(RS)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-p-toluamide

CAS name

3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

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

Dow AgroSciences
Rohm and Haas

Example products using this active

Gavel
Electis
Zoxium 80 WP
Tirms

Formulation and application details

Usually supplied as aqueous flowable concentrates and wettable powders

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.681

Low

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

20000

Ethyl acetate

55700

Acetone

1560

Xylene

n-Heptane

Melting point (°C)

159.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

160

Flashpoint (°C)

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

5.75 X 10⁰³

Calculated

Log P

3.76

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.38

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.013

Low volatility

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

6.59 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

5.1

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

3.9

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral soln: 241.2nm=10034, 212nm=46330
Acidic soln: 241.4=11549, 212.4nm=49596
Alkaline soln: 244.8nm=13300, 218.2nm=29899

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

5.5

Non-persistent

DT₅₀ (lab at 20 °C)

5.5

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

35.2

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2018 dossier DT₅₀ lab studies range 1.87-34.27 days, DT₉₀ range 6.62-115 days, Soils=8; Manufacturers published data field DT₅₀ 2-10 days; Other sources: DT₅₀ 15 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Test conditions equivalent to summer sunlight in New Jersey USA, 42 deg N

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

Value

15.7

Non-persistent

Note

pH sensitive: DT₅₀ 16 days at pH 4, 8 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

6.4

Fast

Water phase only DT₅₀ (days)

Moderately fast

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.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

1224

Notes and range

Manufacturers published data K_oc circa 1000 mL g⁻¹ (E3)

Freundlich

K_f (mL g⁻¹)

13.3

Slightly mobile

K_foc (mL g⁻¹)

1224.2

¹/_n

0.973

Notes and range

EU 2016 dossier kf range 3.36-25.33 mL g⁻¹, K_foc range 815-1431 mL g⁻¹, ¹/_n range 0.973-1.067, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.71

Calculated

Low leachability

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

Value

5.12 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

7.5

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

115

Threshold for concern

CT₅₀ (days)

0.4

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3,5-dichloro-N-(2-carboxy-1-ethyl-1-methyl-2-oxoethyl)-4-methylbenzamide (Ref: RH-163353)

Major fraction

0.150

3,5-dichloro-N-(1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (Ref: RH-127450)

Major fraction

0.151

3,5-dichloro-4-methylbenzoic acid (Ref: RH-24549)

Major fraction

0.338

3,5-dichloro-1,4-benzenedicarboxylic acid3,5-dichloro-terephthalic acid (Ref: RH-1455)

Minor fraction

0.08

3,5-dichloro-4-methylbenzoic acid (Ref: RH-4549)

Major fraction

0.338

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3,5-dichloro-4-hydroxymethylbenzamide (Ref: RH-149736)

RH-9736

3,5-dichloro-4-methylbenzamide (Ref: RH-139432)

RH-9432

4-carboxy-3,5-dichlorobenzamide (Ref: RH-149737)

RH-9737

(3-amino-3-methyl-2-oxo)pentyl-(3,5-dichloro-4-methyl)benzoate (Ref: RH-150721)

RH-0721

Water (a = Hydrolysis, b = Photolysis)

3,5-dichloro-4-hydroxymethylbenzoic acid (Ref: RH-141452)

RH-1452

2-(3,5-dichloro-4-methylphenyl)-4-ethyl-4-methyl-4H-1,3-oxazin-5(6H)-one (Ref: RH-129151)

RH-9151

Water (Hydrolysis)

0.164

3,5-dichloro-N-(3-hydroxy-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (Ref: RH 141288)

RH-1288

Water (Hydrolysis)

3,5-dichloro-N-(1-ethyl-1-methyl-2-oxopropyl)-4-hydroxymethylbenzamide (Ref: RH-141454)

RH-1454

3,5-dichloro-N-(2-carboxy-1-ethyl-1-methyl)-4-methylbenzamide (Ref: RH-141643)

RH-1643

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)

> 50

Dog

High

(ppm diet)

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

> 1474

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5250 mg kg feed⁻¹

Colinus virginianus

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

122.8

Anas platyrhynchos NOEC

Moderate

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

> 1070

Eisenia foetida

Low

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

66.7

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 2 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

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)

> 147

Apis mellifera

Low

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

Chronic as 10-day LC₅₀ µg bee⁻¹ day⁻¹

174.8

Apis mellifera

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

> 300

Aphidius rhopalosiphi

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

> 300

Typhlodromus pyri

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)

0.16

Oncorhynchus mykiss

Moderate

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

0.004

Oncorhynchus mykiss

High

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

> 0.73

Danio rerio

Moderate

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

> 0.78

Daphnia magna

Moderate

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

0.039

Daphnia magna

Moderate

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

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)

0.45

Chironomus riparius

Moderate

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

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

0.017

Lemna gibba

Moderate

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

0.011

Scenedesmus subspicatus

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 5.3

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.5

Dog 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)

None allocated

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

0.3

Rat 90 day SF=100

Dermal penetration studies (%)

4.0-10.0

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

Rapid and almost completely eliminated via bile within 24hrs

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

Eye irritant

Phototoxicant

General human health issues

Liver and thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

zoxamide

French

zoxamide

German

Zoxamide

Danish

zoxamid

Italian

zoxamide

Spanish

zoxamida

Greek

Polish

zoksamid

Swedish

zoxamid

Hungarian

zoxamid

Dutch

Norwegian

Record last updated:	22/08/2024
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