Pinoxaden (Ref: NOA 407855)

Pinoxaden (Ref: NOA 407855)	Last updated: 31/10/2024
(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: Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health High alert: Genotoxic

GENERAL INFORMATION

Description

A herbicide for post-emergence control of annual grass weeds in some cereal crops

Example pests controlled

Annual grasses including blackgrass, bluegrass, common windgrass, reed canary grass, foxtail, Avena spp.

Example applications

Cereals including winter & spring barley, winter wheat, durum wheat, Rye, Triticale

Efficacy & activity

Availability status

Current

Introduction & key dates

2006, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2031

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Finland/Belgium

Date EC 1107/2009 inclusion expires

30/06/2026

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

Morocco

Chemical structure

Isomerism

None

Chemical formula

C₂₃H₃₂N₂O₄

Canonical SMILES

CCC1=CC(=CC(=C1C2=C(N3CCOCCN3C2=O)OC(=O)C(C)(C)C)CC)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

MGOHCFMYLBAPRN-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C23H32N2O4/c1-7-16-13-15(3)14-17(8-2)18(16)19-20(26)24-9-11-28-12-10-25(24)21(19)29-22(27)23(4,5)6/h13-14H,7-12H2,1-6H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
pinoxaden	-

General status

Pesticide type

Herbicide

Substance groups

Phenylpyrazole herbicide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - Toluene max 1 g kg⁻¹

Substance origin

Synthetic

Mode of action

Systemic. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

243973-20-8

EC number

635-361-9

CIPAC number

776

US EPA chemical code

147500

PubChem CID

210326

CLP index number

607-726-00-2

Molecular mass

400.51

PIN (Preferred Identification Name)

IUPAC name

8-(2,6-diethyl-p-tolyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpropionate

CAS name

8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpropanoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Alopecurus myosuroides, Avena sterilis

Physical state

White to beige coloured fine powder

Formulations

Property

Value

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

Greencrop
Syngenta

Example products using this active

Axial
Greencrop Helvick
Aoraki

Formulation and application details

Often supplied as an emulsifiable concentrate 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)

200

at 25 °C

Moderate

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

250000

Acetone

500000

Dichloromethane

1000

Hexane

130000

Toluene

Melting point (°C)

121.1

Boiling point (°C)

>360

Degradation point (°C)

>335

Flashpoint (°C)

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.16

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

2.00 X 10^-04

Low volatility

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

9.20 X 10^-07

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

1.2

24 hr

Volatilisation is not considered critical for air pollution

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

No absorbance >290nm

Surface tension (mN m⁻¹)

45.8

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.5

Non-persistent

DT₅₀ (lab at 20 °C)

0.34

Non-persistent

DT₅₀ (field)

0.6

Non-persistent

DT₉₀ (lab at 20 °C)

1.68

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.086-0.904 days, DT₉₀ range 0.29-3.0 days; field studies range 0.07-1.01 days

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

29.5

Slow

Note

Data is for natural summer sunlight 40 deg N, 29 days of 12hr light/dark cycles

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

Value

14.9

Non-persistent

Note

pH sensitive: DT₅₀ 24 days at pH 4, 25 days at pH 5, 15 days at pH 7, 0.3 days at pH 9, all at 20 °C.

Water-sediment DT₅₀ (days)

0.28

Fast

Water phase only DT₅₀ (days)

0.27

Fast

Sediment phase only DT₅₀ (days)

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

5.9

Moderately mobile

K_foc (mL g⁻¹)

349

¹/_n

1.03

Notes and range

EU dossier K_f range 1.7-10.9 mL g⁻¹, K_foc range 121-852 mL g⁻¹, ¹/_n range 0.93-1.12, Soils=9

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.32

Calculated

Low leachability

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

Value

1.43 X 10^-04

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

1.1

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)

Low risk

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

8-(2,6-diethyl-4-methylphenyl)-tetrahydropyrazolo-1,2-d (Ref: NOA 407854)

Major fraction

0.897

8-(2,6-diethyl-4-methyl-phehyl)-8-hydroxy-tetrahydropyrazolo(1,2-d)(1,4,5)oxadiazepine-7,9-dione (Ref: NOA 447204)

Major fraction

0.306

2,2-dimethyl proprionic acid

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

8-(2,6-diethyl-4-methylphenyl)-tetrahydropyrazolo-1,2-d (Ref: NOA 407854)

Relevant

8-(2,6-diethyl-4-methyl-phehyl)-8-hydroxy-tetrahydropyrazolo(1,2-d)(1,4,5)oxadiazepine-7,9-dione (Ref: NOA 447204)

Relevant

0.01

600

3,5-diethyl-4-(8-hydroxy-7,9-dioxo-hexa-hydro-pyrazolo[1,2-d][1,4,5]oxadiazepine- 8-yl)-benzoic acid (Ref: SYN 504574 )

Relevant

1-ethyl-5-hydroxymethyl-12-oxo-7,8,10,11-tetrahydro-5H,12H-6,9-dioxa-6b,11a-diaza-naphtho[2,1-a]azulene-3-carboxylic acid

Relevant

4-(1,4-dioxo-hexahydro-2,7-dioxa-4a,9a-diaza-benzocyclohepten-3-yl)-3, 5-diethyl-benzoic acid

Relevant

7-ethyl-3-hydroxy-3-methyl-3H-spiro[2-benzofuran-1,8'-pyrazolo[1,2-d] [1,4,5]oxadiazepine]-7',9'-dione-5-carboxylic acid

Relevant

7-methylcarboxy-5-methyl-3-hydroxy-3-methyl-3H-spiro[2-benzofuran-1,8'-pyrazolo[1,2-d][1,4,5]oxadiazepine]-7',9'-dione

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

8-(2,6-diethyl-4-hydroxymethyl-phenyl)-8-hydroxy-tetrahydro-pyrazolo[1,2-d][1,4,5] oxadiazepine-7,9-dione (Ref: SYN 505857)

pinoxaden metabolite M10

Plant

2,2-dimethyl proprionic acid

pivalic acid

Rat; Animal

3,5-diethyl-4-(9-hydroxy-7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-8-yl)-benzoic acid (Ref: SYN 502836)

pinoxaden metabolite M06

Plant

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)

Rabbit

High

(ppm diet)

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

> 500

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

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

> 200

Unknown species

Low

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

> 500

Eisenia foetida corr

Moderate

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

Soil micro-organisms

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

Dose: 0.4 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

9.16

Avena sativa
Vegetative vigour, ER₅₀
as g ha⁻¹

42.0

Lolium perenne
Seeding emergence, ER₅₀
as g ha⁻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)

> 200

Apis mellifera

Low

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

Chronic

Notes

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) a % Mortality at dose 60 g ha⁻¹

5.8

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

6.22

Aphidius rhopalosiphi

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

1.81

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)

10.3

Oncorhynchus mykiss

Moderate

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

3.2

Oncorhynchus mykiss

Moderate

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

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

52.0

Daphnia magna

Moderate

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)

8.3

Americamysis bahia

Moderate

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

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)

3.5

Lemna gibba

Moderate

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

0.91

Skeletonema costatum

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

> 4.63

Rat

Other Mammal toxicity endpoints

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

0.1

Rabbit SF=100

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

0.1

Rabbit SF=100

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

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

0.1

Rabbit SF=100

Dermal penetration studies (%)

0.5-2.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk of dietary exposure
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)

0.1

EU Dir 89/778/EC limit; Calc MAC=300 µg l⁻¹

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

May cause an allergic skin reaction

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H315, H317, H319, H332, H335, H361d
Environment: H400, H412

WHO Classification

III (Slightly hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

pinoxaden

French

pinoxaden

German

Pinoxaden

Danish

pinoxaden

Italian

pinoxaden

Spanish

pinoxaden

Greek

Polish

pinoksaden

Swedish

Hungarian

Dutch

Norwegian

pinoksaden

Record last updated:	31/10/2024
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