Tepraloxydim (Ref: BAS 620H)

Tepraloxydim (Ref: BAS 620H)	Last updated: 22/08/2024
(Also known as: caloxydim; 191819)

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 High alert: GUS: High leachability; Drainflow: Mobile	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description

A post-emergence herbicide for control of annual grass weeds

Example pests controlled

Volunteer cereals; Sterile brome; Blackgrass; Annual meadowgrass; Common couch

Example applications

Oilseed rape; Sugarbeet; Fodder beet; Peas; Field beans; Cabbage; Cauliflower; Linseed; Flax; Carrots; Onions; Leeks

Efficacy & activity

Availability status

Current

Introduction & key dates

1999, first reported & registered

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Expired

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

A chiral molecule with a pair of optical isomers. Substance is racemic.

Chemical formula

C₁₇H₂₄ClNO₄

Canonical SMILES

CCC(=C1C(=O)CC(CC1=O)C2CCOCC2)NOCC=CCl

Isomeric SMILES

CCC(=C1C(=O)CC(CC1=O)C2CCOCC2)NOC/C=C/Cl

International Chemical Identifier key (InChIKey)

IOYNQIMAUDJVEI-ZFNPBRLTSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H24ClNO4/c1-2-14(19-23-7-3-6-18)17-15(20)10-13(11-16(17)21)12-4-8-22-9-5-12/h3,6,12-13,20H,2,4-5,7-11H2,1H3/b6-3+,19-14+

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Cyclohexene oxime herbicide

Minimum active substance purity

920 g/Kg

Known relevant impurities

Substance origin

Synthetic

Mode of action

Broad spectrum, absorbed through leaves and translocated. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

149979-41-9

EC number

604-715-4

CIPAC number

608

US EPA chemical code

121005

PubChem CID

135585373

CLP index number

606-116-00-3

Molecular mass

341.8

PIN (Preferred Identification Name)

rac-(5R)-2-[(1E)-N-{[(2E)-3-chloroprop-2-en-1-yl]oxy}propanimidoyl]-3-hydroxy-5-(oxan-4-yl)cyclohex-2-en-1-one

IUPAC name

(5RS)-2-{(EZ)-1-[(2E)-3-chloroallyloxyimino]propyl}-3-hydroxy-5-perhydropyran-4-ylcyclohex-2-en-1-one

CAS name

2-(1-((((2E)-3-chloro-2-propenyl)oxy)imino)propyl)-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-one

Other status information

Chemical subject to PIC regulations: GB Part 2

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

Lolium rigidum

Physical state

White to beige coloured powder with characteristic odour

Formulations

Property

Value

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

BASF
Calyton
Standon
Teliton

Example products using this active

Aramo
Standon Tonga

Formulation and application details

Often supplied as emulsifiable concentrates that are 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)

430

Moderate

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

450000

Ethyl acetate

460000

Acetone

270000

Methanol

1000

n-Heptane

Melting point (°C)

Boiling point (°C)

>185

Degradation point (°C)

Flashpoint (°C)

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

3.16 X 10⁰¹

Calculated

Log P

1.5

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.28

Dissociation constant pKa) at 25 °C

4.58

Weak acid

Vapour pressure at 20 °C (mPa)

0.027

Low volatility

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

8.74 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

258nm = 11000

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

8.7

Non-persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

29.4

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 5.2-14 days, DT₉₀ range 17-48 days days; field studies DT₅₀ range 45-81 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.7

Note

Soybean seeds, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.5

Moderately fast

Note

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

Value

Stable

Note

Stable pH7-9; DT₅₀ 6.6 days at pH4, 24.4 days at pH 5

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

>100

Stable

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)

0.36

Mobile

K_foc (mL g⁻¹)

22.2

¹/_n

0.928

Notes and range

EU dossier K_f range 0.01-1.47 mL g⁻¹; K_foc range 0.3-77.2 mL g⁻¹; ¹/_n range 0.630-1.236, Soils=9

pH sensitivity

Yes - adsorption increases at lower pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

4.77

Calculated

High leachability

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

Value

2.94 X 10⁰⁰

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-hydroxy-2-(1-iminopropyl)-5-(tetrahydropyran-4-yl)cyclohex-2-en-1-one

Major fraction

0.111

2-ethyl-6-(tetrahydropyran-4-yl)-4,5,6,7-tetrahydrobenzoxasol-4-one

Major fraction

0.100

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-(tetrahydro-pyran-4-yl)-glutaric acid

tepraloxydim diacid; tepraloxydim GP

Plant (straw)

5-hydroxytepraloxydim

5-OH DP

Plant; Rat; Animal

6-OH-DP-2; tepraloxydim oxazole

Plant

3-hydroxy-3-(tetrahydro-pyran-4-yl)-glutaric acid

OH-GP

Plant; Animal

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)

(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)

> 6000 mg kg feed⁻¹

Colinus virginianus

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

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

> 1000

Eisenia foetida

Low

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

> 400

Eisenia foetida

Low

Soil micro-organisms

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

Dose: 2.5 Litres BAS 6200H + 10 Litres Dash

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)

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

> 200

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)

Beneficial insects (Parasitic wasps) as % Mortality

62.5

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as % Mortality

100

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)

82.5

Lepomis macrochirus

Moderate

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

Oncorhynchus mykiss

Moderate

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

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

> 100

Daphnia magna

Low

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

Daphnia magna

Low

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)

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

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

6.5

Lemna gibba

Moderate

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

78.2

Chlorella fusca

Low

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)

> 5.1

Rat 4 hr (nose-only)

Other Mammal toxicity endpoints

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

0.025

Rat SF=200

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

0.4

Rat 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)

0.06

Rat SF=200

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

In humans: Around 70-80% excreted in the urine remainder in the faeces, significant enteroheptaic circulation; In animals: approx. 30% lost in urine.

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver & kidney toxicant
CLP data - suspected carcinogen; US EPA - insufficient data for assessment

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H351, H361fd

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

tepraloxydim

French

tepraloxydim

German

Tepraloxydim

Danish

tepraloxydim

Italian

tepraloxydim

Spanish

tepraloxidim

Greek

Polish

tepraloksydim

Swedish

tepraloxidim

Hungarian

Dutch

tepraloxydim

Norwegian

Record last updated:	22/08/2024
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