Thiencarbazone-methyl (Ref: BYH 18636 )

Thiencarbazone-methyl (Ref: BYH 18636 )	Last updated: 19/09/2024
(Also known as: TCM)

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: GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A herbicide that is often used in mixtures with isoxaflutole for pre-emergence control of grassy and broad-leaved weeds

Example pests controlled

Smartweed; Velvetleaf; Barnyardgrass; Morning glory; Dead nettle; Curly Dock; Hemp; Wild mustard; Foxtail; Lambsquarter

Example applications

Corn; Sweetcorn; Soybean; Beet; Wheat (Spring & Durum); Turf; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

2008, introduced USA

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/09/2029

GB 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

France/Greece

Date EC 1107/2009 inclusion expires

30/09/2024

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

USA, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₁₄N₄O₇S₂

Canonical SMILES

CC1=C(C(=CS1)C(=O)OC)S(=O)(=O)NC(=O)N2C(=O)N(C(=N2)OC)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

XSKZXGDFSCCXQX-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H14N4O7S2/c1-6-8(7(5-24-6)9(17)22-3)25(20,21)14-10(18)16-12(19)15(2)11(13-16)23-4/h5H,1-4H3,(H,14,18)/f/h14H

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Triazolone herbicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

ALS inhibitor, systemic, absorbed by roots and leaves, contact and residual action

CAS RN

317815-83-1

EC number

635-659-9

CIPAC number

797

US EPA chemical code

015804

PubChem CID

11205153

CLP index number

No data found

Molecular mass

390.44

PIN (Preferred Identification Name)

methyl 4-[(3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carbonyl)sulfamoyl]-5-methylthiophene-3-carboxylate

IUPAC name

methyl 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonylsulfamoyl]-5-methylthiophene-3-carboxylate

CAS name

methyl 4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate

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

White crystalline powder

Related substances & organisms

thiencarbazone

Formulations

Property

Value

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

Bayer CropScience

Example products using this active

Adengo
velocity
Capreno

Formulation and application details

Available in a wide range of different formulations including oil dispersions, flowable concentrates and water dispersable granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

436

Moderate

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

230

Ethanol

0.15

n-Hexane

190

Toluene

9540

Acetone

Melting point (°C)

205

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

231

Flashpoint (°C)

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

1.05 X 10^-02

Calculated

Log P

-1.98

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.51

Dissociation constant pKa) at 25 °C

3.0

Weak acid

Vapour pressure at 20 °C (mPa)

8.8 X 10^-11

Low volatility

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

7.88 X 10^-14

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Acid: 214nm = 27519, 228nm = 13125
Neutral: 214nm = 28596, 234nm = 14058
Basic: 211nm = 34453, 228nm = 29144

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

11.6

Non-persistent

DT₅₀ (lab at 20 °C)

51.5

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 3.1-38.8 days, DT₉₀ range 10.6-176.7 days; Field studies: DT₅₀ 17days mean, 45days max, n=17; Other data: DT₅₀ range 3.2 to 55 days (F4)

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

90.6

Stable

Note

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

Value

146

at 25 °C

Persistent

Note

pH4: 118 days, PH9 153 days at 25 °C

Water-sediment DT₅₀ (days)

26.2

Fast

Water phase only DT₅₀ (days)

21.3

Slow

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)

Moderately mobile

K_oc (mL g⁻¹)

100

Notes and range

Other data: K_oc range 59.9 to 236 mL g⁻¹ (F4)

Freundlich

K_f (mL g⁻¹)

2.01

Moderately mobile

K_foc (mL g⁻¹)

100

¹/_n

0.906

Notes and range

EU dossier kf range 0.40-6.23 mL g⁻¹, K_foc range 43-190 mK/g, ¹/_n range 0.886-0.932, soils = 5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.46

Calculated

Transition state

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

Value

1.03 X 10^-01

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

24.2

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)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-(aminosulfonyl)-5-methyl-3-thiophenecarboxylic acid (Ref: AE1395853)

Major fraction

0.212

6-methylthienol(3,4-d)isothiazol-3(2H)-one 1,1-dioxide

thiencarbazone-methyl-triazolinone carboxamide

thiencarbazone

Major fraction

3-thiophene carboxylic acid, 4((((4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl)amino)sulfonyl)-5-methyl- (Ref: AE1394083)

Major fraction

0.536

3H-1,2,4-triazol-3-one, 2,4-dihydro-5-methoxy-4-methyl- (Ref: AE1277106)

Major fraction

0.206

3-thiophenecarboxylic acid, 4-(aminosulfonyl)-5-methyl-, methyl ester (Ref: AE1364547)

Major fraction

0.156

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)

3-thiophene carboxylic acid, 4((((4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl)amino)sulfonyl)-5-methyl- (Ref: AE1394083)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Thiencarbazone-methyl-OMT-glycoside; M12

Plant

Thiencarbazone-methyl-hydroxy; M13

Plant

Thiencarbazone-methyl-hydroxy-glycoside; M14

Plant

Dimethyl carbamate; M24

Animal

Thiencarbazone-methyl-triazoldione; M26

Water; Animal

Thiencarbazone-methyl-dicarboxy sulfonamide; M25

Surface water

6-methylthienol(3,4-d)isothiazol-3(2H)-one 1,1-dioxide

Thiencarbazone-methyl thienosaccharine; M05

Plant; Rat; Animal

4-(((3-methoxy-5-oxo-4,50dihydro-1H-1,2,4-triazol-1-yl)carbonyl)amino)sulfonyl)-5-methylthiophene-3-carboxylic acid

Thiencarbazone-methyl N desmethyl carboxylic acid; M02

Plant

4-(aminosulfonyl)-5-(hydroxymethyl)thiophene-3-carboxylic acid

Thiencarbazone-methyl-hydroxy-sulphonamide-carboxylic acid; MO4

Plant

6-(hydroxymethyl)thienol(3,4-d)isothiazol-3(2H)-one 1,1-dioxide

Thiencarbazone-methyl-hydroxy-thienosaccharine; M06

Plant

Thiencarbazone-methyl N desmethyl; M07

Plant; Animal

Thiencarbazone-methyl-N-desmethyl-glycoside; M08

Plant

Thiencarbazone-methyl-desmethyl-hydroxy; M09

Plant

Thiencarbazone-methyl-desmethyl-hydroxy-glycoside; M10

Plant

5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one

Thiencarbazone-methyl-OMT; M11; O-methyltriazolinone

Plant

Thiencarbazone-methyl-triazolinone carboxamide; M20

Plant; Rat; Animal

Thiencarbazone-methyl-methyl carbamate; M23

Animal; Rat

Thiencarbazone-methyl-hydroxy-sulfonamide; M16

Plant

Thiencarbazone-methyl-hydroxy-sulfonamide-glycoside; M17

Plant

Thiencarbazone-methyl-hydroxy-sulfonamide-acetyl-glycoside; M18

Plant

Thiencarbazone-methyl-hydroxy-sulfonamide-glyceric acid; M19

Plant

Thiencarbazone-methyl-MMT-glucoside; M22

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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)

> 699 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)

Soil micro-organisms

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

Dose: 0.3 mg kg⁻¹ DW soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

> 1000

Folsomia candida

Non-target plants

5.3

Sunflowers
Vegetative vigour, ER₅₀
as mL product ha⁻¹ (SC450: Conc 0.045 kg ha⁻¹)

2.9

Ryegrass
Seedling emergence, ER₅₀
as mL product ha⁻¹ (SC450: Conc 0.045 kg ha⁻¹)

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 199

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)

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

> 45

Aphidius rhopalosiphi

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

> 45

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)

> 104

Oncorhynchus mykiss

Low

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

4.8

Pimephales Promelas

Moderate

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

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

> 98.6

Daphnia magna

Moderate

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

3.54

Daphnia magna

Moderate

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)

0.0008

Lemna gibba

High

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

0.17

Pseudokirchneriella subcapitata

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.018

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.23

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

None allocated

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

Not applicable

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

0.12

Dermal penetration studies (%)

0.3-2.5

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Very low risk to consumers

Occupational

Very low risk to operaters

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL levels for some commodities subject to change in late 2021

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Readily excreted (within 48 hrs) in the urine (~50%) and faeces (~50%). Largelty unmetabolised.

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible kidney, bladder and urinary tract toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

thiencarbazone-methyl

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

tienkarbazon-metyl

Hungarian

Dutch

Norwegian

Record last updated:	19/09/2024
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