Tralkoxydim (Ref: PP 604)

Tralkoxydim (Ref: PP 604)	Last updated: 20/11/2020
(Also known as: tralkoxydime; tralcoxidime)

GENERAL INFORMATION

Description

A foliar applied oxime herbicide for grass weed control in cereals

Example pests controlled

Wild oats; Ryegrass; Canary grass (suppression); Paradoxa grass (suppression); Annual phalaris (suppression)

Example applications

Cereals including wheat, rye, triticale, barley

Efficacy & activity

Availability status

Current

Introduction & key dates

1986, UK; 1999, USA

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

UK LERAP status

None (may vary with mixtures)

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Spain/Portugal

Date EC 1107/2009 inclusion expires

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

Australia

Chemical structure

Isomerism

Talkoxydim is a chiral molecule which exists in two isomeric forms: (E-) and (Z-).

Chemical formula

C₂₀H₂₇NO₃

Canonical SMILES

CCC(=C1C(=O)CC(CC1=O)C2=C(C=C(C=C2C)C)C)NOCC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

DQFPEYARZIQXRM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H27NO3/c1-6-16(21-24-7-2)20-17(22)10-15(11-18(20)23)19-13(4)8-12(3)9-14(19)5/h8-9,15,22H,6-7,10-11H2,1-5H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Cyclohexadione

Minimum active substance purity

780-900 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, systemic, absorbed by leaves and translocated to growing points. Inhibits fatty acid synthesis. Inhibition of acetyl CoA carboxylase (ACCase)

CAS RN

87820-88-0

EC number

CIPAC number

544

US EPA chemical code

121000

PubChem CID

91746

Molecular mass

329.43

PIN (Preferred Identification Name)

(5E)-2-[(1E)-N-ethoxypropanimidoyl]-3-hydroxy-5-(2,4,6-trimethylphenyl)cyclohex-2-en-1-one

IUPAC name

(RS)-2-[(EZ)-1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one

CAS name

2-(1-(ethoxyimino)propyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-one

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Avena fatua, Avena sterilis ludoviciana, Setaria viridis

Physical state

White solid

Formulations

Property

Value

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

Alpha Tralkoxydim 250SC
Fleck 25 SC
Grasp
Strimma
Splendor

Example products using this active

Ellagret SA
Greencrop
Makhteshim-Agan
Nufarm
Standon
Teliton

Formulation and application details

Often supplied as a soluble concentrate or water soluble granules 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)

6.1

Low

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

89000

Acetone

25000

Methanol

213000

Toluene

110000

Ethyl acetate

Melting point (°C)

110

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

129

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.26 X 10⁰²

Calculated

Log P

2.1

Low

Bulk density (g ml⁻¹)

1.16

Dissociation constant pKa) at 25 °C

4.3

Weak acid

Vapour pressure at 20 °C (mPa)

3.70 X 10^-04

Low volatility

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

2.00 X 10^-05

Non-volatile

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

Neutral solution: 220nm = 16454, 258nm = 11500, 285nm = 10347, 310nm = 2569
Acidic solution: 220nm = 16518, 258nm = 13577, 310nm = 3156
Basic solution: 220nm = 15577, 283nm = 23583, 310nm = 886

Surface tension (mN m⁻¹)

53.0

at 20°C 90% soln

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.9

Non-persistent

DT₅₀ (lab at 20 °C)

2.6

Non-persistent

DT₅₀ (field)

1.9

Non-persistent

DT₉₀ (lab at 20 °C)

25.7

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 1.2-10.8 days (normalised), DT₉₀ range 3.7-103 days; Other sources: DT₅₀ (1) 1.9 days (B5), (2) 10-20 days (US3), (3) 3 days (R3)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

4.9

Note

Wheat leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

5.8

Moderately fast

Note

Data for natural summer sunlight, Florida USA, 25-35 deg N

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

Value

140

Persistent

Note

pH sensitive: DT₅₀ 9 days at pH 5, stable at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

110.7

Slow

Water phase only DT₅₀ (days)

68.4

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

1.3

Moderately mobile

K_oc

120

Notes and range

EU dossier K_d range 0.15-2.2 mL g⁻¹, K_oc range 35-314 mL g⁻¹, Soils=6

Freundlich

K_f

1.07

Moderately mobile

K_foc

102

¹/_n

0.99

Notes and range

EU dossier kf range 0.16-2.2 mL g⁻¹, K_foc range 30-290 mL g⁻¹, ¹/_n range 0.98-1.1, Soils=6

pH sensitivity

Adsorption inversely related to soil pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.56

Calculated

Low leachability

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

Value

1.23 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-(2,4,6-trimethylphenyl)pentanedioic acid (Ref: R173642)

Soil

0.172

Major fraction, Relevant

4-(2-(1-ethoxyimino)propyl)-3-hydroxy-2-cyclohexene-1-one-5-yl)-3-5-dimethyl benzoic acid (Ref: R223068)

Soil

0.125

Major fraction, Relevant

2-ethyl-4,5,6,7-tetrahydro-4-oxo-6-(2,4,6-trimethylphenyl)benzoxazole (Ref: R163434)

Soil

0.075

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-hydroxy-2-propionyl-5-(2,4,6-trimethylphenyl)cyclohex-2-enone (Ref: R159368)

Water (Photolysis)

3-hydroxy-2-(1-iminopropyl)-5-(2,4,6-trimethylphenyl)cyclohex-2-enone (Ref: R158378)

Water (Photolysis); Water/sediment

3-hydroxy-2-(imino-1-propyl)-5-dimethyl-4-hydroxymethylphenyl)cyclohex-2-enone (Ref: R400307)

Plant

2,6-dimethyl-4-(2-ethyl-4,5,6,7-tetrahydrobenzoxazol-4-one)benzyl alcohol (Ref: R237434)

Plant

3,5-dimethyl-4-(2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-enone-S-yl)benzyl alcohol (Ref: R209490)

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

934

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 4.4

Rat

High

(ppm diet)

> 50

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

2024

Alectoris rufa

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

1018 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

14.3

Colinus virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 6.1

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

4.6

Oncorhynchus mykiss

Moderate

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

> 175.0

Daphnia magna

Low

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

2.1

Daphnia magna

Moderate

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)

1.0

Lemna gibba

Moderate

Non-target plants

Zea mays
Vegetative vigour (shoot length), ER₅₀
as g ha⁻¹

180

Lolium perenne
Seedling emergence (dry shoot weight), ER₅₀
as g ha⁻¹

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

> 5.1

Pseudokirchneriella subcapitata

Moderate

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

> 5.1

Unknown species

Low

Honeybees (Apis spp.)

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

> 100

Low

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

> 117

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)

> 1000

Eisenia foetida

Low

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

450

>
Typhlodromus pyri

% Effect

9.2

Mortality [Dose: 450 kg ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

450

>
Aphidius rhopalosiphi

% Effect

10.3

Mortality [Dose: 45 kg ha⁻¹]
Aphidius rhopalosiphi

Soil micro-organisms

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

Dose: 2.5 mg kg⁻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)

934

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.5

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.005

Dog SF=100

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

0.01

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)

0.005

Dog SF=100

Dermal penetration studies (%)

0.1-1.5

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

European MRLs

EU MRL pesticide database

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Liver and adrenals toxicant
Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin
Health effects may be delayed
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H302, H351
Environment: H411

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R62, R63
Xn - Harmful: R22
N - Dangerous for the environment: R51, R53

EC Safety Classification

S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 2588

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

tralkoxydim

French

tralkoxydime

German

Tralkoxydim

Danish

tralkoxydim

Italian

tralcoxydim

Spanish

tralkoxidim

Greek

Polish

tralkoksydim

Swedish

Hungarian

Dutch

Record last updated:	20/11/2020
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