Hexythiazox (Ref: NA 73)

Hexythiazox (Ref: NA 73)	Last updated: 28/08/2024
(Not known by any other names)

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 Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Daphnia chronic ecotoxicity: High	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

An acaricide used for the control of eggs and larvae of many mites on a wide variety of food crops

Example pests controlled

Tetranychid mites

Example applications

Fruit including apples, pears, stone fruit, citrus, grapes; Nuts; Turf; Cotton; Cucumber

Efficacy & activity

Availability status

Current

Introduction & key dates

1982, first reported; 1985, first registered Japan

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2029

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Finland/Sweden

Date EC 1107/2009 inclusion expires

31/01/2027

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, Morocco

Chemical structure

Isomerism

A molecule with 2 chiral centres. Substance is racemic.

Chemical formula

C₁₇H₂₁ClN₂O₂S

Canonical SMILES

CC1C(SC(=O)N1C(=O)NC2CCCCC2)C3=CC=C(C=C3)Cl

Isomeric SMILES

C[C@H]1[C@@H](SC(=O)N1C(=O)NC2CCCCC2)C3=CC=C(C=C3)Cl

International Chemical Identifier key (InChIKey)

KYOUEHWYDNYHAL-IOORBXIBSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H21ClN2O2S/c1-11-15(12-7-9-13(18)10-8-12)23-17(22)20(11)16(21)19-14-5-3-2-4-6-14/h7-11,14-15H,2-6H2,1H3,(H,19,21)/t11-,15+/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Acaricide, Insecticide

Substance groups

Carboxamide acaricide; Carboximide insecticide; Thiazolidine acaricide; Thiazolidine insecticide

Minimum active substance purity

976 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Non-systemic with contact and stomach action. Mite growth inhibitor affecting CHS1.

CAS RN

78587-05-0

EC number

616-638-3

CIPAC number

439

US EPA chemical code

128849

PubChem CID

13218777

CLP index number

No data found

Molecular mass

352.88

PIN (Preferred Identification Name)

IUPAC name

(4RS,5RS)-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide

CAS name

(4R,5R)-rel-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolidinecarboxamide

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)

10A

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Brevipalpus phoenicis, Panonychus ulmi, Tetranychus urticae

Physical state

White to beige coloured powder

Formulations

Property

Value

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

Anorgachim SA
Hellafarm SA
Nippon soda
FCC

Example products using this active

Hexythiazox 10 WP
Bulk 10 WP
Nissorun 10WP
Ocaren

Formulation and application details

Often supplied as a wettable powder that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.1

Low

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

159000

Acetone

22000

Ethanol

17000

Methanol

4600

n-Heptane

Melting point (°C)

105.4

Boiling point (°C)

222

Degradation point (°C)

300

Flashpoint (°C)

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

4.68 X 10⁰²

Calculated

Log P

2.67

at 25 °C

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.31

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.33 X 10^-03

Low volatility

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

1.19 X 10^-02

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

From soil surface

Negligible

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

Neutral solution: 202nm = 24220,225nm = 18390
Acidic solution: 225.5nm = 18310
Basic solution: 224.5nm = 16990

Surface tension (mN m⁻¹)

71.8

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

23.7

Non-persistent

DT₅₀ (field)

17.7

Non-persistent

DT₉₀ (lab at 20 °C)

103.5

Persistent

DT₉₀ (field)

59.6

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 7.8-56.0 days, n=6, DT₉₀ range 32.2-117.2 days, field studies DT₅₀ range 10-29 days, DT₉₀ range 35-96 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

12.0

Note

Green bean pods, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

8.0

Note

Published literature RL₅₀ range 3.62-18.7, 3 crops, various matricies, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

11.5

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

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

207

Non-mobile

K_foc (mL g⁻¹)

9455

¹/_n

0.99

Notes and range

EU dossier K_f range 61-416, K_foc range 6875-12823 mL g⁻¹, ¹/_n range 0.94-1.1, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.03

Calculated

Low leachability

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

Value

5.32 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

3.62

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

1100

Whole fish

Threshold for concern

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

5-(4-chlorophenyl)-N-(4-oxocyclohexyl)-4-methyl-2-oxothiazolidine-3-carboxamide (Ref: PT-1-9)

Major fraction

0.211

trans-5-(4-chlorophenyl)-4-methyl-2-oxothiazolidine-3-carboximide (Ref: PT-1-2)

Major fraction

0.395

trans-5-(4-chlorophenyl)-4-methyl-2-oxothiazolidine (Ref: PT-1-3)

Minor fraction

0.092

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

5-(4-chlorophenyl)-N-( cis-4-hydroxylcyclohexyl)-4-methyl-trans-2-oxothiazolidine-3-carboxamide

PT-1-8 ( cis)

Rat (Urine, Faeces)

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)

> 70

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 523 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

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

> 52.5

Eisenia foetida corr

Moderate

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

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect at 42 days
Carbon mineralisation: No significant adverse effect at 14 days

Dose: 1.7 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)

> 200

Apis mellifera

Low

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

> 112

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 48 hr

300

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

65.9

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)

3.2

Lepomis macrochirus

Moderate

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

0.04

Oncorhynchus mykiss

Moderate

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

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

> 0.36

Daphnia magna

Moderate

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

0.0061

Daphnia magna

High

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)

1.7

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)

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

> 0.4

Scenedesmus subspicatus

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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.0

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.03

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)

0.009

Dermal penetration studies (%)

1-10

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Occupational exposure may occur through inhalation and dermal contact

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL levels for some commodities subject to change in late 2021

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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 toxicant
US EPA - prossible human carcinogen

Handling issues

Property

Value and interpretation

General

Dust may form an explosive mix with air
Not oxidising
Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 9

CLP classification 2013

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

TRANSLATIONS

Language

Name

English

hexythiazox

French

hexythiazox

German

Hexythiazox

Danish

hexythiazox

Italian

exitiazox

Spanish

hexitiazox

Greek

hexythiazox

Polish

heksytiazoks

Swedish

hexytiazox

Hungarian

hexitiazox

Dutch

hexythiazox

Norwegian

Record last updated:	28/08/2024
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