Oxathiapiprolin (Ref: DPX-QGU42)

Oxathiapiprolin (Ref: DPX-QGU42)	Last updated: 24/02/2021
(Also known as: QGU42)

GENERAL INFORMATION

Description

A novel fungicide for use as a seed treatment against various fungal diseases on crops including potatoes and vegetables

Example pests controlled

Downy mildew, Late blight, Phytophthora root and stem blight

Example applications

Fruiting vegetables including tomatoes, aubergines, peppers, and curcubits; Lettuce; Grapes; Melons; Potatoes; Herbs

Efficacy & activity

Availability status

Current

Introduction & key dates

2013

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

03/03/2027

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Ireland/Poland

Date EC 1107/2009 inclusion expires

03/03/2027

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

Also used in

Chemical structure

Isomerism

Chemical formula

C₂₄H₂₂F₅N₅O₂S

Canonical SMILES

CC1=CC(=NN1CC(=O)N2CCC(CC2)C3=NC(=CS3)C4=NOC(C4)C5=C(C=CC=C5F)F)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

IAQLCKZJGNTRDO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C24H22F5N5O2S/c1-13-9-20(24(27,28)29)31-34(13)11-21(35)33-7-5-14(6-8-33)23-30-18(12-37-23)17-10-19(36-32-17)22-15(25)3-2-4-16(22)26/h2-4,9,12,14,19H,5-8,10-11H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Piperidinyl thiazole isoxazoline

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

Systemic, preventative with residual disease control. It acts via an oxysterol binding protein.

CAS RN

1003318-67-9

EC number

CIPAC number

US EPA chemical code

PubChem CID

56945145

Molecular mass

539.53

PIN (Preferred Identification Name)

rac-1-(4-(4-((5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl)piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethan-1-one

IUPAC name

1-(4-(4-((5RS)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl)-1-piperidyl)-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone

CAS name

1-(4-(4-(5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl)-1-piperidinyl)-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone

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)

U15

Examples of recorded resistance

Physical state

Pure material: off-white crystalline solid (98.9 %)

Formulations

Property

Value

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

Orondis
Zorvec

Example products using this active

DuPont
Syngenta

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.1749

Low

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

n-Hexane

5800

o-Xylene

352900

Dichloromethane

162800

Acetone

Melting point (°C)

146.4

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

289.5

Flashpoint (°C)

Not expected to self-ignite; Not highly flammable

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

4.57 X 10⁰³

Calculated

Log P

3.66

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.141 X 10^-03

Low volatility

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

3.521 X 10^-03

Non-volatile

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

pH 1.8: 257 & 258 nm = 14055
pH 7.0: 256 & 257 nm = 13863
pH 10.5: 258 & 259 nm = 16384

Surface tension (mN m⁻¹)

65.53

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

121.2

Persistent

DT₅₀ (lab at 20 °C)

121.2

Persistent

DT₅₀ (field)

71.3

Moderately persistent

DT₉₀ (lab at 20 °C)

503.1

Very persistent

DT₉₀ (field)

344.5

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 59.4-217.3 days, DT₉₀ range 197.2-1224 days; Field studies DT₅₀ range 31.5-138.5 days, DT₉₀ range 75.8-682 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

15.4

Slow

Note

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

Value

Stable

Note

Stable at all relevant pH values

Water-sediment DT₅₀ (days)

36.7

Moderately fast

Water phase only DT₅₀ (days)

9.5

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

165.4

Non-mobile

K_oc

9673.8

Notes and range

EU dossier K_d range 61.5-518 mL g⁻¹, K_oc range 5123-17852 mL g⁻¹, soils=6

Freundlich

K_f

79.1

Non-mobile

K_foc

6242.6

¹/_n

0.97172

Notes and range

EU dossier K_f range 53.9-1322 mL g⁻¹, K_foc range 4350-45586 mL g⁻¹, ¹/_n range 0.8877-1.1207, soils = 6

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.38

Calculated

Low leachability

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

Value

8.64 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid (Ref: IN-E8S72)

Soil

0.0672

Minor fraction, Relevant

1-(2-(4-(4-(5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl)-1-piperidinyl)-2-oxoethyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (Ref: IN-RAB06)

Soil

0.135

Major fraction, Relevant

1-(4-(4-(5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl)-4-hydroxy-1-piperidinyl)-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone (Ref: IN-RDT31)

Soil

0.094

Minor fraction, Relevant

4-(4-(5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl)piperidine (Ref: IN-QPS10)

Soil

0.087

Minor fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

131

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

> 1013

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1280 mg kg⁻¹ BW/day

Colinus virginianus

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

106.7

Colinus virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.69

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.46

Oncorhynchus mykiss 88 day

Moderate

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

> 0.67

Daphnia magna

Moderate

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

=> 0.75

Daphnia magna

Moderate

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

> 0.64

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.56

Chironomus riparius 48 hr

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.11

Chironomus riparius

Moderate

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

2.80

Chironomus riparius

Moderate

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

> 0.79

Lemna gibba

Moderate

Non-target plants

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

> 0.351

Skeletonema costatum

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

Apis mellifera

Low

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

> 40.26

Apis mellifera

Moderate

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)

=> 1000

Eisenia foetida 56 days

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

25.0

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

200

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

116.1

Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 15.59 mg kg⁻¹ soil 28 days

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)

>= 5.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

1.04

Rat 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)

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

0.31

Rat SF=100

Dermal penetration studies (%)

0.7

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk based on proposed uses

Occupational

Low risk based on proposed uses

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver & gall bladder toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

oxathiapiprolin

French

oxathiapiproline

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	24/02/2021
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