Fenpicoxamid (Ref: XDE 777)

Fenpicoxamid (Ref: XDE 777)	Last updated: 19/01/2021
(Also known as: X772777; XR-777; UK 2A procide; Antibiotic UK 2A procide; GF-2925; lyserphenvalpyr)

SUMMARY

A novel antibiotic fungicide with a new class of chemistry that is currently progressing through the EU regulatory system. 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.

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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK authorisation for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

UK/France

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

Also used in

Chemical structure

Isomerism

Isomeric

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 group

Unclassified

Minimum active substance purity

750 g kg⁻¹

Known relevant impurities

EFSA DAR: None declared

Substance origin

Synthetic

Mode of action

A Qi inhibitor fungicide

CAS RN

517875-34-2

EC number

None allocated

CIPAC number

991

US EPA chemical code

PubChem CID

121494114

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not known

Examples of recorded resistance

Physical state

White powdery solid

Formulations

Property

Value

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

Example products using this active

Dow Agrosciences

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)

Not expected to self ignite; Not highly flammable

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

2.51 X 10⁰⁴

Calculated

Log P

4.4

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

786

Non-mobile

K_oc

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

470.8

Non-mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.434

Major fraction; Relevant

(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)

Soil

0.389

Major fraction; Relevant

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

Soil

0.354

Major fraction; Relevant

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)

Soil

0.160

Major fraction; Relevant

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

Soil

0.101

Major fraction; Relevant

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

Soil

0.107

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one
Note: Transient metabolite

X11963422

Soil

X763024

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

18.36

Low potential

CT₅₀ (days)

No data

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0022

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00037

Pimephales promelas 32 day

High

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

0.00093

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

> 2.0

Oats
Vegetative vigour, ER₅₀
as g ha⁻¹

> 2.0

Sunflower
Seedling emergence, ER₅₀
as g ha⁻¹

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

> 0.522

Pseudokirchneriella subcapitata

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)

> 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)

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)

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

9.93

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

3.97

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

400

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

129

=
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

Nitrogen transformation: No significant adverse effect

Dose: 0.438 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)

> 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

Mice 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

Mice 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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

CLP classification 2013

Environment: H400, H410

EC Risk Classification

EC Safety Classification

WHO Classification

UN Number

Waste disposal & packaging

TRANSLATIONS

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English

fenpicoxamid

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Record last updated:	19/01/2021
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