Kresoxim-methyl (Ref: BAS 490F)

Kresoxim-methyl (Ref: BAS 490F)	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 Moderate alert: Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

A fungicide for the control of scab and other fungal diseases on a wide range of crops

Example pests controlled

Scab; Mildews; Blast; Sheath blight;

Example applications

Sugarbeet; Fruit including apples, grapes, pears; Curcubit vegetables; Pecans

Efficacy & activity

Availability status

Current

Introduction & key dates

1983, discovered; 1996, first introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2029

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/France

Date EC 1107/2009 inclusion expires

31/12/2024

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

Australia, USA, Morocco

Chemical structure

Isomerism

Isomeric

Chemical formula

C₁₈H₁₉NO₄

Canonical SMILES

CC1=CC=CC=C1OCC2=CC=CC=C2C(=NOC)C(=O)OC

Isomeric SMILES

CC1=CC=CC=C1OCC2=CC=CC=C2/C(=N\OC)/C(=O)OC

International Chemical Identifier key (InChIKey)

ZOTBXTZVPHCKPN-HTXNQAPBSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H19NO4/c1-13-8-4-7-11-16(13)23-12-14-9-5-6-10-15(14)17(19-22-3)18(20)21-2/h4-11H,12H2,1-3H3/b19-17+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
kresoxim-methyl	Unstated isomer

General status

Pesticide type

Fungicide, Other substance

Other bioactivity & uses

Bactericide

Substance groups

Strobilurin fungicide; Methoxyiminoacetate strobilurin fungicide

Minimum active substance purity

934

Known relevant impurities

EU dossier - Methanol <5 g kg⁻¹; Methyl chloride <1 g kg⁻¹; Toluene < 1 g kg⁻¹

Substance origin

Synthetic

Mode of action

Protective, curative, eradicative action and long residual effects, acts by binding to Qo site blocking electron transfer and respiration of the fungi

CAS RN

143390-89-0

EC number

604-351-6

CIPAC number

568

US EPA chemical code

129111

PubChem CID

6112114

CLP index number

607-310-00-0

Molecular mass

313.35

PIN (Preferred Identification Name)

IUPAC name

methyl (E)-methoxyimino[α-(o-tolyloxy)-o-tolyl]acetate

CAS name

methyl (αE)-α-(methoxyimino)-2-((2-methylphenoxy)methyl)benzeneacetate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

off-white crystalline powder

Formulations

Property

Value

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

AgriGuard
BASF
Standon

Example products using this active

Stroby WG
Kresoxy WG
Beem WG
Candit

Formulation and application details

Often supplied as wettable granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.0

Low

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

1720

n-Heptane

14900

Methanol

217000

Acetone

123000

Ethyl acetate

Melting point (°C)

102

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

310

Flashpoint (°C)

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

2.51 X 10⁰³

Calculated

Log P

3.4

at 25 °C

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - substance almost completely metabolised in goats with no fat soluble residues

Density (g ml⁻¹)

1.26

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

2.30 X 10^-03

Low volatility

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

3.60 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Absorption occurs above 290nm

Surface tension (mN m⁻¹)

72.8

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

0.87

Non-persistent

DT₅₀ (field)

1.0

Non-persistent

DT₉₀ (lab at 20 °C)

1.12

Non-persistent

DT₉₀ (field)

1.0

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.37-1.85 days, DT₉₀ 1.58-1.85 days; Field studies DT₉₀ > 1day; Other sources: 4 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

6.5

Note

Cucumber fruit, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

7.1

Note

Published literature RL₅₀ range 2.6-11.0 days, 7 field & undercover grown crops, various matrices, n=14

Aqueous photolysis DT₅₀ (days) at pH 7

Value

18.2

Slow

Note

Continuous irradiation

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

Value

Moderately persistent

Note

pH sensitive: DT₅₀ 822 days at pH 5, 0.38 days at pH 9

Water-sediment DT₅₀ (days)

1.3

Fast

Water phase only DT₅₀ (days)

0.85

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

[Pepper: No observed residue decay after 21 days storage @ 4 DegC, dark conditions; Field study], [Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study], [Waxed apples: No observed residue decay after 40 days @ 18-25 DegC, shady conditions; Field study]

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)

4.26

Moderately mobile

K_foc (mL g⁻¹)

308

¹/_n

0.975

Notes and range

EU Dossier K_f range 2.6-7.74, kfoc range 219-372 mL g⁻¹, ¹/_n range 0.95-0.99, Soils=5

pH sensitivity

Adsorption increases as pH decreases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.00

Calculated

Low leachability

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

Value

3.35 X 10^-04

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

6.72

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)

220

Whole fish

Threshold for concern

CT₅₀ (days)

0.37

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

kresoxim diacid

(E)-methoxyamino(alpha-(o-tolyloxy)-o-tolyl)acetic acid (Ref: BF 490-1)

Major fraction

0.838

hydroxylated kresoxim-methyl (Ref: BF 490-4)

Minor fraction

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

BF 490-15; 490M54

Plant

490M17

Plant

BF 490-8; 490M18

Rat (Urine)

490M19

Rat (Urine)

490M56

Rat (Urine)

490M58

Animal

490M59

Animal

BF 490-2

Plant

BF 490-9

Rat; Plant

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)

> 146

Rat

Moderate

(ppm diet)

> 2000

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

1500

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Anas platyrhynchos

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

51.7

Colinus virginianus NOEC

Moderate

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 469

Eisenia foetida corr

Moderate

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

Soil micro-organisms

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

Dose: 2.0 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 900

Carrot Cabbage Corn Oats Peas
Vegetative vigour, 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)

> 110

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)

Slightly harmful at dose 150 g ha⁻¹

Chrysoperla carnea

Beneficial insects (Lacewings)

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

> 900

Aphidius rhopalosiphi

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

> 900

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)

0.19

Oncorhynchus mykiss

Moderate

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

0.013

Oncorhynchus mykiss

Moderate

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

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

0.186

Daphnia magna

Moderate

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

0.032

Daphnia magna

Moderate

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

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

0.047

Americamysis bahia

High

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)

0.301

Lemna gibba

Moderate

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

0.063

Ankistrodesmus spp.

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.6

Rat

Other Mammal toxicity endpoints

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

0.4

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)

0.9

Rat 90 day SF=100

Dermal penetration studies (%)

0.3-13

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risk to bystanders identified

Occupational

No unacceptable risk to operators and other workers identified

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

; ; ; ;

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 carcinogen but this is desputed by some sources; US EPA - likely to be human carcinogen; CLP data - suspected carcingen
May damage esophagus or gastrointestinal tract
Possible liver toxicant

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 9
Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H351
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

kresoxim-methyl

French

kresoxim-methyl

German

Kresoxim-methyl

Danish

kresoxim-methyl

Italian

kresoxim metile

Spanish

kresoxim-metil

Greek

kresoxim-methyl

Polish

krezoksym metylowy

Swedish

kresoximmetyl

Hungarian

kresoxim-methyl

Dutch

kresoxim-methyl

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