Sedaxane

Sedaxane	Last updated: 09/12/2019
(Not known by any other names)

GENERAL INFORMATION

Description

Novel seed treatment for the control of pathogens in crops such as wheat and cotton

Example pests controlled

Rhizoctonia spp.; Fusarium patch; Head smut; Barley stripe; Ustilago spp.; Common bunt; Phoma; Dwarf bunt

Example applications

Cereals; Soybeans; OSR; Potatoes; Rice; Sugarbeet; Sunflowers; Cotton; Pulses

Efficacy & activity

Availability status

Current

Introduction & key dates

2008

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2024

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

31/01/2024

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
✓		✓	✓		✓	✓		✓

Also used in

U.S.; Canada; China; Chile; Mexico; Uraguay; Australia; Argentina

Chemical structure

Isomerism

Sedaxane is a chiral molecule. The technical material is an isomeric mixture of the two cis- (0-20%)and two-trans (80-100%) isomers.

Chemical formula

C₁₈H₁₉F₂N₃O

Canonical SMILES

CN1C=C(C(=N1)C(F)F)C(=O)NC2=CC=CC=C2C3CC3C4CC4

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

XQJQCBDIXRIYRP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H19F2N3O/c1-23-9-14(16(22-23)17(19)20)18(24)21-15-5-3-2-4-11(15)13-8-12(13)10-6-7-10/h2-5,9-10,12-13,17H,6-8H2,1H3,(H,21,24)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Pyrazole

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

Broad spectrum, Succinate dehydrogenase inhibitor

CAS RN

874967-67-6

EC number

CIPAC number

833

US EPA chemical code

129223

PubChem CID

11688533

Molecular mass

331.4

PIN (Preferred Identification Name)

mix of: rac-N-{2-[(1R,2S)-1,1'-bi(cyclopropan)]-2-ylphenyl}-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and 20–0% rac-N-{2-[(1R,2R)-1,1'-bi(cyclopropan)]-2-ylphenyl}-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide

IUPAC name

mix of: trans-isomers 2′-[(1RS,2SR)-1,1′-bicycloprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxanilide and 20–0% 2 cis-isomers 2′-[(1RS,2RS)-1,1′-bicycloprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxanilide

CAS name

N-[2-[1,1'-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide

Other status information

Australian APVMA No. 64098; PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

None identified

Physical state

Related substances & organisms

difenoconazole

metalaxyl-M

Formulations

Property

Value

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

Vibrance

Example products using this active

Syngenta Crop Protection

Formulation and application details

Formulated as a treament for seeds

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

14.0

Low

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

410000

Acetone

500000

Dichloromethane

2000

Ethyl acetate

70000

Toluene

Melting point (°C)

121.4

Boiling point (°C)

>270

Degradation point (°C)

270

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰³

Calculated

Log P

3.3

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

6.5 X 10^-05

Low volatility

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

4.0 X 10^-06

Non-volatile

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

Neutral: 225nm=17233, 265nm=5996, 295nm=874
Acidic: 225nm=17423, 265nm=5683, 295nm=851
Alkaline: 225nm=17393, 265nm=5833, 195nm=955

Surface tension (mN m⁻¹)

48.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

108

Persistent

DT₅₀ (lab at 20 °C)

108

Persistent

DT₅₀ (field)

100

Persistent

DT₉₀ (lab at 20 °C)

361

Persistent

DT₉₀ (field)

170

DT₅₀ modelling endpoint

Note

EU dossier DT₅₀ lab studies range 52.4-1000 days, DT₉₀ range 174-301 days; Field studies DT₅₀ range 54.6-188 day, DT₉₀ range 413->1000 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

Note

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

Value

Note

Water-sediment DT₅₀ (days)

866

Stable

Water phase only DT₅₀ (days)

17.3

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

7.9

Slightly mobile

K_foc

534

¹/_n

0.87

Notes and range

EU dossier K_f range 2.00-16.7 mL g⁻¹, K_foc range 202-666 mL g⁻¹, ¹/_n range 0.81-0.91, soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.54

Calculated

Transition state

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

Value

1.74 X 10^-01

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

3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (Ref: CSCD465008)

Soil

0.319

Major fraction, Relevant

pyrazole acid (Ref: CSAA798670)

Soil

0.145

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

pyrazole amide (Ref: SYN 508272)

Soil; Water (photolysis)

Ref: CSCD668094

Water (photolysis)

Ref: CSCD668095

Water (photolysis)

Ref: CSCD728931

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

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)

> 103.8

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1068

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

96.3

Colinus virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.10

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.165

Pimephales promelas 33 day

Moderate

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

6.10

Daphnia magna

Moderate

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

0.75

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)

Non-target plants

> 100

-
Seedling emergence, ER₅₀
A5 Onion, Oat, Ryegrass, Corn; Sugarbeet; Lettice, Tomato

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

1.90

Moderate

Algae - Chronic 96 hour NOEC, growth (mg 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)

> 4.0

Apis mellifera

Moderate

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)

> 500

Eisenia foetida corr

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

228

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

27.9

Aphidius rhopalosiphis

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

160

>
Typhlodromus pyri

% Effect

Soil micro-organisms

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)

> 2000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.25

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.11

Rat SF=100

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

0.28

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)

0.3

Rat SF=100

Dermal penetration studies (%)

0.01-0.12

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Liver & thyroid toxicant
May cause loss of bodyweight
USEPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

Carcinogen category 2: R45
N - Dangerous for the environment: R50/53

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

sedaxane

French

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Polish

Swedish

Hungarian

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Record last updated:	09/12/2019
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