Fenpicoxamid (Ref: XDE 777)

Fenpicoxamid (Ref: XDE 777)	Last updated: 17/07/2024
(Also known as: X772777; XR-777; UK 2A procide; Antibiotic UK 2A procide; GF-2925; lyserphenvalpyr; Inatreq)

SUMMARY

A novel antibiotic fungicide with a new class of chemistry. It has a low human health risk with no major concerns being identified in the initial data set. It appears to degrade quickly in soils and is unstable in water. It also has a low toxicity to birds but is a much higher risk to aquatic organisms.

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: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A pre-emergence antibiotic fungicide for use on cereals to control a range of foliar diseases

Example pests controlled

Foliar diseases including Mycosphaerella graminicola (Septoria tritici), Black Slgatoka

Example applications

Spring and winter cereals including soft wheat, durum wheat, rye and tritical; Rice; Bananas

Efficacy & activity

Based on manufacturers information products are considered to be sufficiently effective and have no unacceptable effects on plant or plant products

Availability status

Current

Introduction & key dates

2016, introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

11/10/2028

UK LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/Bulgaria

Date EC 1107/2009 inclusion expires

11/10/2028

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

Chemical structure

Isomerism

Molecule has absolute stereochemistry with unspecified optical activity

Chemical formula

C₃₁H₃₈N₂O₁₁

Canonical SMILES

CC1C(C(C(=O)OCC(C(=O)O1)NC(=O)C2=NC=CC(=C2OCOC(=O)C(C)C)OC)CC3=CC=CC=C3)OC(=O)C(C)C

Isomeric SMILES

C[C@H]1[C@@H]([C@H](C(=O)OC[C@H](C(=O)O1)NC(=O)C2=NC=CC(=C2OCOC(=O)C(C)C)OC)CC3=CC=CC=C3)OC(=O)C(C)C

International Chemical Identifier key (InChIKey)

QGTOTYJSCYHYFK-XSARVHFWSA-N

International Chemical Identifier (InChI)

InChI=1S/C31H38N2O11/c1-17(2)28(35)42-16-41-26-23(39-6)12-13-32-24(26)27(34)33-22-15-40-30(37)21(14-20-10-8-7-9-11-20)25(19(5)43-31(22)38)44-29(36)18(3)4/h7-13,17-19,21-22,25H,14-16H2,1-6H3,(H,33,34)/t19-,21+,22+,25-/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Unclassified substance

Minimum active substance purity

750 g kg⁻¹

Known relevant impurities

EFSA DAR: None declared

Substance origin

Synthetic

Mode of action

A QiI fungicide that acts at the quinone inside (Qi) site of the inner membrane of complex III

CAS RN

517875-34-2

EC number

815-084-1

CIPAC number

991

US EPA chemical code

PubChem CID

121494114

CLP index number

No data found

Molecular mass

614.64

PIN (Preferred Identification Name)

(3S,6S,7R,8R)-8-benzyl-3-(4-methoxy-3-(((2-methylpropanoyl)oxy)methoxy)pyridine-2-carboxamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate

IUPAC name

(2-(((3R,7R,8R,9S)-7-benzyl-9-methyl-8-(2-methylpropanoyloxy)-2,6-dioxo-1,5-dioxonan-3-yl)carbamoyl)-4-methoxypyridin-3-yl)oxymethyl 2-methylpropanoate

CAS name

propanoic acid, 2-methyl-, ((4-methoxy-2-((((3S,7R,8R,9S)-9-methyl-8-(2-methyl-1-oxopropoxy)-2,6-dioxo-7-(phenylmethyl)-1,5-dioxonan-3-yl)amino)carbonyl)-3-pyridinyl)oxy)methyl ester

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 powdery solid

Formulations

Property

Value

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

Dow Agrosciences

Example products using this active

Univoq

Formulation and application details

Supplied as a suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.041

unstable

Low

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

250000

1,2-dichloroethane

180000

Acetone

18000

Xylene

130000

Ethyl acetate

Melting point (°C)

158.3

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

246

Flashpoint (°C)

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

2.51 X 10⁰⁴

Calculated

Log P

4.4

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

4.4

Vapour pressure at 20 °C (mPa)

1.2 X 10^-04

Low volatility

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

2.38 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

pH 2: maxima at 2.09nm and 245nm
pH 7: maxima at 214nm and 276nm
pH 10: maxima at 211nm and 327nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Generally considered not to be readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

3.5

Non-persistent

DT₅₀ (lab at 20 °C)

3.5

Non-persistent

DT₅₀ (field)

9.91

Non-persistent

DT₉₀ (lab at 20 °C)

12.7

Non-persistent

DT₉₀ (field)

68.4

DT₅₀ modelling endpoint

3.5

Note

EU 2018 dossier: Lab studies DT₅₀ range 2.0-6.0 days, DT₉₀ range 6.8-19.8 days, Soils=4; Field studies DT₅₀ range 4.1-50.9 days, DT₉₀ range 17.8-194.0 days, Soils =5

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

0.35

Fast

Note

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

Value

0.92

at 25 °C

Non-persistent

Note

pH 4: 7.1 days at 25 °C, pH 9: 0.024 days at 25 °C

Water-sediment DT₅₀ (days)

0.76

Fast

Water phase only DT₅₀ (days)

0.26

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)

786

Non-mobile

K_oc (mL g⁻¹)

53233

Notes and range

EU 2018 dossier: K_d range 349-1278 mL g⁻¹, K_doc range 8961-134720 mL g⁻¹, Soils=7

Freundlich

K_f (mL g⁻¹)

470.8

Non-mobile

K_foc (mL g⁻¹)

19731

¹/_n

0.820

Notes and range

EU 2018 dossier: K_f range 9.36-2472 mL g⁻¹, K_foc range 936-63394 mL g⁻¹, ¹/_n range 0.608-1.066, Soils=7

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.29

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

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

0.261

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)

18.36

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-hydroxy-4-methoxypyridine-2-carboxylic acid (Ref: X696476)

Major fraction

0.434

(3S,6S,7R,8R)-8-benzyl-3-(((3-hydroxy-4-methoxypyridin-2-yl)carbonyl)amino)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate (Ref: X642188)

Major fraction

0.389

N-((3-hydroxy-4-methoxypyridin-2-yl)carbonyl)serine (Ref: X12264475)

Major fraction

0.354

N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypyridine-2-carboxamide (Ref: X696872)

Major fraction

0.160

3-hydroxy-4-methoxypyridine-2-carboximide (Ref: X12313581)

Major fraction

0.101

(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one (Ref: X119634522)

Major fraction

0.107

(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one (Ref: X11963422)

Transient

Ref: X763024

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

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

9.93

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen transformation: No significant adverse effect

Dose: 0.438 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

3.97

Folsomia candida corr

Non-target plants

> 2.0

Oats
Vegetative vigour, ER₅₀
as g ha⁻¹

> 2.0

Sunflower
Seedling emergence, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 202.4

Apis mellifera

Low

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

> 303

Apis mellifera

Low

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

0.71

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

> 129

Aphidius rhopalosiphi

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

400

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)

0.0022

Oncorhynchus mykiss

High

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

0.00037

Pimephales promelas 32 day

High

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

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

0.00093

Daphnia magna

High

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

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)

0.15

Chironomus riparius 48 hr

Moderate

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)

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

> 0.522

Pseudokirchneriella 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)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.53

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.05

Mouse SF=100

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

1.8

Rabbit SF=100

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

0.2

Rabbit SF=833 corr

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

0.05

Mouse SF=833 corr

Dermal penetration studies (%)

0.2-6.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No significant risks anticipated for proposed patterns of use

Occupational

Estimated risks acceptable, PPE/PPC recommended

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

Rapidly eliminated via faeces and urine in first 24hrs

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 and kidney toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

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Record last updated:	17/07/2024
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