Tembotrione (Ref: AE 0172747)

Tembotrione (Ref: AE 0172747)	Last updated: 22/08/2024
(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 High alert: Drainflow: Mobile	Ecotoxicity Moderate alert: Fish chronic ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

A post-emergence herbicide for the control of a broad spectrum of broad-leaved and grassy weeds in corn and other crops

Example pests controlled

Barnyardgrass; Crabgrass; Foxtail; Goosegrass; Nutsedge; Wild oats; Johnsongrass; Junglerice; nightshade; pigweed; Ragweed; Velvetleaf; Waterhemp

Example applications

Maize; Sweetcorn

Efficacy & activity

Availability status

Current

Introduction & key dates

2007, registered Austria & USA

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/07/2028

UK LERAP status

Crop 5m - See Authorisation for Crop LERAP Details

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

31/12/2026

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

Brazil, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₇H₁₆ClF₃O₆S

Canonical SMILES

CS(=O)(=O)C1=C(C(=C(C=C1)C(=O)C2C(=O)CCCC2=O)Cl)COCC(F)(F)F

Isomeric SMILES

International Chemical Identifier key (InChIKey)

IUQAXCIUEPFPSF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H16ClF3O6S/c1-28(25,26)13-6-5-9(15(18)10(13)7-27-8-17(19,20)21)16(24)14-11(22)3-2-4-12(14)23/h5-6,14H,2-4,7-8H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Aroylcyclohexanedione herbicide

Minimum active substance purity

945 g kg⁻¹

Known relevant impurities

EU dossier - toluene <10g kg⁻¹; NCN < 1g kg⁻¹

Substance origin

Synthetic

Mode of action

Broad spectrum

CAS RN

335104-84-2

EC number

608-879-8

CIPAC number

790

US EPA chemical code

012801

PubChem CID

11556911

CLP index number

606-149-00-3

Molecular mass

440.82

PIN (Preferred Identification Name)

2-{2-chloro-4-(methanesulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione

IUPAC name

2-{2-chloro-4-mesyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione

CAS name

2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione

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

Physical state

Beige powder

Formulations

Property

Value

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

Bayer CropScience

Example products using this active

Laudis
Capreno

Formulation and application details

Often available as an oil dispersion formulation

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

71000

High

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

8200

Ethanol

47600

n-Hexane

75700

Toluene

180200

Ethyl acetate

Melting point (°C)

123

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

150

Flashpoint (°C)

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

8.13 X 10^-02

Calculated

Log P

-1.09

at 24 °C

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.56

Dissociation constant pKa) at 25 °C

3.18

Weak acid

Vapour pressure at 20 °C (mPa)

1.1 X 10^-05

Low volatility

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

1.71 X 10^-10

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 203nm = 31021, 232nm = 14224, 284nm = 13800, 291nm = 12960
Acidic solution: 205nm = 31015, 231nm = 15370, 283nm = 14303, 291nm = 12937
Basic solution: 217nm = 17015, 258nm = 22080, 291nm = 13415

Surface tension (mN m⁻¹)

64.2

at 20°C 947g l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

14.5

Non-persistent

DT₅₀ (lab at 20 °C)

14.5

Non-persistent

DT₅₀ (field)

2.72

Non-persistent

DT₉₀ (lab at 20 °C)

45.4

Moderately persistent

DT₉₀ (field)

50.2

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4.2-87.2 days, DT₉₀ range 14.2-262 days; field studies DT₅₀ range 1.8-2.9 days, DT₉₀ range 27.8-105 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

56.3

Stable

Note

Data for test conditions sterile water at pH 7, equivalent to DT₅₀ of 269 days in natural summer light, Athens, Greece (37 deg N)

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

108

Slow

Water phase only DT₅₀ (days)

Stable

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)

1.59

Mobile

K_foc (mL g⁻¹)

¹/_n

0.907

Notes and range

EU dossier kf range 0.51-3.62 (47.2 for organic soil) mL g⁻¹; ¹/_n range 0.871-0.977 (0.993 for organic soil), Soils=6

pH sensitivity

Adsorption increases as pH decreases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.95

Calculated

Low leachability

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

Value

2.10 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

2.93

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

Based on LogP < 3

Low risk

CT₅₀ (days)

No data

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]-benzoic acid (Ref: AE-0456148)

Major fraction

0.724

2-chloro-4(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)phenol (Ref: AE-0968400)

Major fraction

0.149

xanthenedione (Ref: AE 0941989)

Photolysis

glutaric acid (Ref: AE 1275213)

Photolysis

2-chloro-1-methoxy-4-(methyl sulfonyl)-3-[(2,2,2-trifluoroethoxy) methyl]benzene (Ref: AE 1124336)

Minor fraction

0.087

Bayer verified

AE 0172747-carboxybenzyl alcohol; tembotrione metabolite M02 (Ref: AE 1392936)

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)

2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]-benzoic acid (Ref: AE-0456148)

Not relevant

0.2

1200

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

AE 0172747-benzylalcohol; tembotrione metabolite M08

Animal

AE 0172747-dihydroxy benzophenone; tembotrione metabolite M09

Animal

Ref: AE 1444744

AE 0172747-4-hydroxy; tembotrione metabolite M10

Animal; Plant

AE 0172747-5-hydroxy; tembotrione metabolite M11

Animal

AE 0172747-4,5-hydroxy; tembotrione metabolite M12

Animal

AE 0172747-4-hydroxy benzyl alcohol; tembotrione metabolite M13

Animal

AE 0172747-ketohydroxy hexanoic acid; tembotrione metabolite M14

Animal

Ref: AE 1392936

AE 0172747-carboxybenzyl alcohol; tembotrione metabolite M02

Plant

glutaric acid (Ref: AE 1275213)

tembotrione metabolite M04; pentanedioic acid

Surface water (Photolysis)

Ref: AE 01417268

AE 0172747-4,6-dihydroxy; tembotrione metabolite M05

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2500

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)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1788 mg kg bw⁻¹ day⁻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)

1.25

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 0.5 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

62.5

Folsomia candida

Non-target plants

61.2

Brassica oleracea
Vegetative vigour, ER₅₀
as mL product ha⁻¹ (Laudis: Conc 44g l⁻¹)

76.8

Brassica oleracea
Seedling emergence, ER₅₀
as mL product ha⁻¹ (Laudis: Conc 44g l⁻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)

> 92.8

Apis mellifera

Moderate

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

Chronic

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

11.26

Aphidius rhopalosiphi

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

57.24

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)

> 100

Oncorhynchus mykiss

Low

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

0.604

Pimephales promelas 34 day

Moderate

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

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

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

5.0

Daphnia magna

Moderate

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.1

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)

0.006

Lemna gibba

High

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

0.38

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)

> 2500

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.58

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.0004

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

0.1

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

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

0.0007

Dermal penetration studies (%)

2-5

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk to bystanders and residents

Occupational

PPE/PPC required to minimise risks

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

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

US EPA - weak evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H317, H373, H361d
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

tembotrione

French

German

Danish

Italian

Spanish

tembotriona

Greek

Polish

tembotrion

Swedish

Hungarian

Dutch

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