Sintofen (Ref: SC 2053)

Sintofen (Ref: SC 2053)	Last updated: 31/10/2024
(Also known as: cintofen; sintofene)

SUMMARY

Sintofen is a plant growth regulator. It is highly soluble in water, is non-volatile and a low potential of leaching to groundwater. It is persistent in both soil and aquatic systems. It has a moderate mammalian toxicity and a high potential for bioaccumulation. Its toxicity to aquatic organisms is low to moderate and it is moderately toxic to birds, earthworms and honeybees.

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: Persistent; Potential for particle bound transport: High	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

A plant growth regulator used for the chemical hybridisation (sterilisation) of wheat

Example pests controlled

Growth

Example applications

Wheat

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1990, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Czech Republic/France

Date EC 1107/2009 inclusion expires

15/07/2026

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

Chemical structure

Isomerism

None

Chemical formula

C₁₈H₁₅CIN₂O₅

Canonical SMILES

CC1=CC=C(C=C1)N2C3=C(C(=CC=C3)OCCOC)C(=O)C(=N2)C(=O)O

Isomeric SMILES

International Chemical Identifier key (InChIKey)

QLMNCUHSDAGQGT-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H15ClN2O5/c1-25-9-10-26-14-4-2-3-13-15(14)17(22)16(18(23)24)20-21(13)12-7-5-11(19)6-8-12/h2-8H,9-10H2,1H3,(H,23,24)/f/h23H

2D structure diagram/image available?

Yes

General status

Pesticide type

Plant Growth Regulator

Substance groups

Unclassified pesticide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - 2-methoxyethanol and N,N-dimethylformamide

Substance origin

Synthetic

Mode of action

Cereal hybridising agent, absorbed through leaves and translocated

CAS RN

130561-48-7

EC number

603-426-0

CIPAC number

717

US EPA chemical code

PubChem CID

10915750

CLP index number

No data found

Molecular mass

374.8

PIN (Preferred Identification Name)

1-(4-chlorophenyl)-5-(2-methoxyethoxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid

IUPAC name

1-(4-chlorophenyl)-1,4-dihydro-5-(2-methoxyethoxy)-4-oxocinnoline-3-carboxylic acid

CAS name

1-(4-chlorophenyl)-1,4-dihydro-5-(2-methoxyethoxy)-4-oxo-3-cinnolinecarboxylic acid

Other status information

PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not known

Herbicide Resistance Class (WSSA MoA class)

Not known

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Cream to yellow powder

Formulations

Property

Value

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

Example products using this active

Croisor 100

Formulation and application details

Usually supplied as a liquid and applied using a boom type sprayer

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

800

High

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

100

Methanol

Ethyl acetate

460

Acetone

1.0

Heptane

Melting point (°C)

Decomposes before melting

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

274

Flashpoint (°C)

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

1.00 X 10^-01

Calculated

Log P

-1.0

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.46

Dissociation constant pKa) at 25 °C

4.92

Weak acid

Vapour pressure at 20 °C (mPa)

3.5 X 10^-07

Low volatility

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

1.64 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

Acidic solution: No absorption
Basic solution: 238nm = 13087, 360nm = 10921

Surface tension (mN m⁻¹)

75.1

20.3°C 90% soln

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

230

Persistent

DT₅₀ (lab at 20 °C)

207

Persistent

DT₅₀ (field)

198.5

Persistent

DT₉₀ (lab at 20 °C)

786

Very persistent

DT₉₀ (field)

500

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 130-328 days, DT₉₀ range 433-1089 days; field studies DT₅₀ range 45-218 days, DT₉₀ >1 year

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

134

Stable

Note

Negligible under real conditions

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

2369

(second phase)

Stable

Water phase only DT₅₀ (days)

8.23

Moderately fast

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)

42.2

Slightly mobile

K_foc (mL g⁻¹)

2902

¹/_n

0.868

Notes and range

EU dossier K_f range 5.34-186.6 mL g⁻¹, K_foc range 376-18848 mL g⁻¹, ¹/_n range 0.809-0.965

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.23

Calculated

Low leachability

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

Value

2.87 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly 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)

No data

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

1-(-4’-chlorophenyl)-1,4-dihydro-5-(2’’-hydroxy-ethoxy)-4-oxo-cinnoline-3-carboxylate (Ref: SC 3095)
Note: Rat oral LD50 > 5000 mg/kg

desmethyl sintofen

Rat (Urine, Faeces)

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)

> 12.6

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1439

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 642 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)

Eisenia foetida

Moderate

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

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 7.5 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 1500

Lettuce OSR Carrot
Vegetative vigour, ER₅₀
as g ha⁻¹

> 1500

Lettuce OSR Carrot
Seedling 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)

> 100

Apis mellifera

Low

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 48 hr

4760

Aphidius rhopalosiphi

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

1460

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)

570

Oncorhynchus mykiss

Low

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

100

Oncorhynchus mykiss

Low

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

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

238

Daphnia magna

Low

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

7.03

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)

4.6

Lemna gibba

Moderate

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

36.9

Pseudokirchneriella subcapitata

Low

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.27

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.091

Rat SF=100

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

None allocated

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

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

0.165

Rat SF=100

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

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

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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

Possible bladder, urinary tract and kidney toxicant
CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H351
Environment: H411

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

sintofen

French

sintofen

German

Sintofen

Danish

sintofen

Italian

sintofen

Spanish

sintofen

Greek

Polish

sintofen

Swedish

Hungarian

Dutch

Norwegian

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