Cinidon-ethyl (Ref: BAS 615H)

Cinidon-ethyl (Ref: BAS 615H)	Last updated: 23/12/2020
(Also known as: cinidon-ethyl)

SUMMARY

Cinidon-ethyl is a post-emergence herbicide that has EU approval for use. It has a low aqueous solubility, is relatively volatile with a low tendency to leach to groundwater. It is slightly mobile. It is not persistent in soil or water systems. Cinidon-ethyl has a low mammalian toxicity and is not expected to bioaccumulate. It is moderately toxic to earthworms but more toxic to aquatic organisms. It is relatively non- toxic to honeybees.

GENERAL INFORMATION

Description

A herbicide for post-emergence control of annual broad-leaved weeds

Example pests controlled

Nettles; Docks; Chickweed; Groundsel

Example applications

Cereals including wheat, rye, triticale

Efficacy & activity

Availability status

Current

Introduction & key dates

1998, UK

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Hungary/UK

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Chemical structure

Isomerism

Isomeric - exists in the E- and Z-forms

Chemical formula

C₁₉H₁₇Cl₂NO₄

Canonical SMILES

CCOC(=O)C(=CC1=C(C=CC(=C1)N2C(=O)C3=C(C2=O)CCCC3)Cl)Cl

Isomeric SMILES

CCOC(=O)/C(=C/C1=C(C=CC(=C1)N2C(=O)C3=C(C2=O)CCCC3)Cl)/Cl

International Chemical Identifier key (InChIKey)

NNKKTZOEKDFTBU-YBEGLDIGSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H17Cl2NO4/c1-2-26-19(25)16(21)10-11-9-12(7-8-15(11)20)22-17(23)13-5-3-4-6-14(13)18(22)24/h7-10H,2-6H2,1H3/b16-10-

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Dicarboximide

Minimum active substance purity

940 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Contact action, selective and acts by protox-inhibition

CAS RN

142891-20-1

EC number

CIPAC number

598

US EPA chemical code

PubChem CID

5851439

Molecular mass

394.3

PIN (Preferred Identification Name)

ethyl (2Z)-2-chloro-3-[2-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)phenyl]prop-2-enoate

IUPAC name

ethyl (Z)-2-chloro-3-[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)phenyl]acrylate

CAS name

ethyl (2Z)-2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenyl]-2-propenoate

Other status information

Chemical subject to PIC regulations

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

Physical state

White crystalline powder

Formulations

Property

Value

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

Lotus
Bingo
Orbit
Solar

Example products using this active

BASF
Nufarm

Formulation and application details

Usually supplied as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.057

Low

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

213000

Acetone

8000

Methanol

84000

Toluene

2000

n-Heptane

Melting point (°C)

112.5

Boiling point (°C)

360

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.51 X 10⁰⁵

Calculated

Log P

5.4

High

Bulk density (g ml⁻¹)

1.4

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.01

Low volatility

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

6.91 X 10^-02

Non-volatile

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

290nm = 11000, 300nm = 5800

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.3

Non-persistent

DT₅₀ (lab at 20 °C)

1.3

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 0.6-1.9 days, DT₉₀ range 6-22 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

2.3

Moderately fast

Note

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

Value

1.5

Non-persistent

Note

pH sensitive: DT₅₀ 5 days at pH 5, 54 mins at pH 9 all at 20 °C

Water-sediment DT₅₀ (days)

0.2

Fast

Water phase only DT₅₀ (days)

0.1

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

87.7

Slightly mobile

K_foc

3262

¹/_n

Notes and range

EU dossier Soils=4

pH sensitivity

Adsorption decreases as pH increases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.06

Calculated

Low leachability

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

Value

1.93 X 10^-04

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(Z)-2-chloro-3-(2-chloro-5-(1,3,dioxo-4,5,6,7-tertahydroisoindol-2-yl)phenyl)acrylic acid

Soil

0.600

Major fraction, Not relevant

(Z)-2-chloro-3-(2-chloro-5-(((2-hydroxycarbonyl)cyclohexen-1-yl)carbonylamino)phenyl)acrylic acid

Soil

0.460

Major fraction, Not relevant

2-(N-(3-((1Z)-2-carboxy-2-chlorovinyl)-4-chlorophenyl)carbamoy)--hydroxycyclohex-1-enecarboxylic acid

Soil

0.210

Major fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

cyclohexene-1,2-dicarboxylic acid

615M20

Water (a=Hydrolysis), (b=Photolysis)

a=0.599 @ pH7; b=0.794

ethyl (2Z)-3-(3-amino-6-chlorophenyl)-2-chloroprop-2-enoate

615M16

Water (a=Hydrolysis), (b=Photolysis)

a=0.249 @ pH7; b=0.143

(Z)-2-chloro-3-[2-chloro-5-(((2-hydroxycarbonyl)cyclohexen-1-yl)carbonylamino)phenyl]acrylic acid ethyl ester

615M07

Water (Hydrolysis)

0.261 @ pH7

cyclohexene-1,2-dicarboxylic anhydride

615M21

Water (Hydrolysis)

0.241 @ pH9

(2Z)-3-(3-amino-6-chlorophenyl)-2-chloroprop-2-enoic acid

615M10

Water (Hydrolysis)

0.349 @ pH9

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2200

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)

> 5000 ppm

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

200

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

1.0

Oncorhynchus mykiss

Moderate

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

59.2

Daphnia magna

Moderate

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

0.11

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)

0.174

Lemna gibba

Moderate

Non-target plants

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

0.021

Pseudokirchneriella subcapitata

Moderate

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

21.9

Unknown species

Low

Honeybees (Apis spp.)

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

> 200

Low

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)

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

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

% Effect

0 / -1

Mortality / Fecundity [Dose: 0.25 kg formulation ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

9.8 / 13.2

Mortality / Fecundity [Dose: 0.25 kg formulation ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: Field rate 28 days

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)

> 2200

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

5.3

Rat

Other Mammal toxicity endpoints

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

0.01

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)

0.02

Dog 90 day SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk of dietary exposure

Occupational

MRLs

European

EU MRL pesticide database

Notes

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317, H351
Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40
Xn - Harmful: R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S24, S37, S46, S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

cinidon-ethyl

French

cinidon-ethyl

German

Cinidon-ethyl

Danish

cinidon ethyl

Italian

cinidon etile

Spanish

cinidon etil

Greek

Polish

cinidon etylowy

Swedish

cinidonetyl

Hungarian

kinidon-etil

Dutch

Record last updated:	23/12/2020
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