Fenhexamid (Ref: KBR 2738)

Fenhexamid (Ref: KBR 2738)	Last updated: 22/08/2024
(Also known as: TM-402; fenhexamide)

SUMMARY

Fenhexamid is a foliar fungicide. It has a low aqueous solubility, a low risk of leaching to groundwater and is relatively volatile. It is not persistent in soil or aquatic systems. It has a low mammalian toxicity and these is a slight concern regarding its potential to bioaccumulate. No serious human health risks have been identified. It is moderately toxic to birds, most aquatic organisms and earthworms. The risk to honeybees is low.

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 acute ecotoxicity: Moderate; Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A foliar fungicide used to control Botrytis spp. and some other pathogens in fruit, vegetables and ornamentals

Example pests controlled

Botrytis cinerea, Monilinia spp., Sclerotinia spp.

Example applications

Strawberries; Grapes; Kiwi fruit; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1989, discovered; 1998, first reported & marketed

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2030

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Belgium/Czech Republic

Date EC 1107/2009 inclusion expires

31/12/2030

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

None

Chemical formula

C₁₄H₁₇Cl₂NO₂

Canonical SMILES

CC1(CCCCC1)C(=O)NC2=C(C(=C(C=C2)O)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

VDLGAVXLJYLFDH-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H17Cl2NO2/c1-14(7-3-2-4-8-14)13(19)17-9-5-6-10(18)12(16)11(9)15/h5-6,18H,2-4,7-8H2,1H3,(H,17,19)/f/h17H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fenhexamid	-

General status

Pesticide type

Fungicide

Substance groups

Analide fungicide

Minimum active substance purity

>975 g kg⁻¹

Known relevant impurities

EU dossier - Toluene < 1g kg⁻¹; 4-amino-2,3-dichlorphenol < 3 g kg⁻¹

Substance origin

Synthetic

Mode of action

Foliar applied with protective action. Disrupts membrane function. Inhibits spore germination.

CAS RN

126833-17-8

EC number

422-530-5

CIPAC number

603

US EPA chemical code

090209

PubChem CID

213031

CLP index number

616-111-00-8

Molecular mass

302.20

PIN (Preferred Identification Name)

N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexane-1-carboxamide

IUPAC name

2',3'-dichloro-4'-hydroxy-1-methylcyclohexanecarboxanilide

CAS name

N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide

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

White powder

Formulations

Property

Value

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

Bayer CropScience
Arvesta Corp
Arysta LifeScience

Example products using this active

Teldor
Decree
Elevate
fenhexamid 500 WG

Formulation and application details

Supplied in a variety of formulations including suspension concentrates, water dispersible granules and wettable powders.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

24.0

Low

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

160000

Acetone

31000

Dichloromethane

100

n-Hexane

5700

Toluene

Melting point (°C)

153.8

Boiling point (°C)

230

Degradation point (°C)

230

Flashpoint (°C)

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

3.24 X 10⁰³

Calculated

Log P

3.51

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.34

Dissociation constant pKa) at 25 °C

7.3

Vapour pressure at 20 °C (mPa)

4.00 X 10^-04

Low volatility

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

5.00 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

From soil surface

Negligible

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

203nm=41340, 291nm=28101

Surface tension (mN m⁻¹)

63.0

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.43

Non-persistent

DT₅₀ (lab at 20 °C)

0.43

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

1.16

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.09-8.13 days, DT₉₀ range 0.54-2.54 days, Other sources: DT₅₀ 25 days (DW2)

Dissipation rate RL₅₀ (days) on plant matrix

Value

7.7

Note

Strawberry fruit, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

9.0

Note

Published literature RL₅₀ range 4.8-14.8 days, 4 field & undercover grown crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.05

Fast

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 for 30 days at 25 °C

Water-sediment DT₅₀ (days)

10.9

Fast

Water phase only DT₅₀ (days)

4.92

Moderately fast

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)

No data

Moderately mobile

K_oc (mL g⁻¹)

475

Notes and range

Other sources: 700 mL g⁻¹ (DW3)

Freundlich

K_f (mL g⁻¹)

10.13

Slightly mobile

K_foc (mL g⁻¹)

733.5

¹/_n

0.85

Notes and range

EU dossier K_f range 2.45-15.79 mL g⁻¹, kfoc range 313-1226 mL g⁻¹, ¹/_n range 0.762-0.896, Soils=10

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.42

Calculated

Low leachability

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

Value

5.09 X 10^-05

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

7.4

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)

185

Whole fish

Threshold for concern

CT₅₀ (days)

0.98

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

deschlorofenhexamid

Minor fraction

0.068

biphenyl-fenhexamid

Minor fraction

0.088

N-(2,3-dichloro-4-hydroxyphenyl)-4-hydroxy-1-methyl-cyclohexanecarboximide (Ref: KBR 2738 M06)

N-(2,3-dichloro-4-methyoxyphenyl)-1-methylcyclohexanecarboximide (Ref: KBR 2738 M09)

7-chloro-2-(1-methylcyclohexyl)-6-benzoxazole (Ref: KBR 2738 M10)

N-(2,3-dichloro-4-hydroxyphenyl)-3-hydroxy-1-methyl-cyclohexanecarboximide (Ref: KBR 2738 M16)

N-(2-chloro-4-hydroxyphenol)-1-methyl cyclohexanecarboxamide (Ref: KBR 2738 M12)

N-(3-chloro-4-hydroxyphenol)-1-methyl cyclohexanecarboxamide (Ref: KBR 2738 M13)

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-(2,3-dichloro-4-(beta-D-glucopyranosyl-oxy)phenyl)-2-hydroxy-1-methylcyclohexane-carboximde (Ref: KBR 2738 M04)

2-hydroxy-fenhexamid glucoside

Plant

N-(2-chloro-4-hydroxyphenol)-1-methyl cyclohexanecarboxamide (Ref: KBR 2738 M12)

2-monochlorofenhexamid

Water

N-(2,3-dichloro-4-hydroxyphenyl)-4-hydroxy-1-methyl-cyclohexanecarboximide (Ref: KBR 2738 M06)

4-hydroxy-fenhexamid

Rat; Animal; Plant; Water

7-chloro-2-(1-methylcyclohexyl)-6-benzoxazole (Ref: KBR 2738 M10)

fenhexamid benzoxazole

Water

N-(2,3-dichloro-4-hydroxyphenyl)-3-hydroxy-1-methyl-cyclohexanecarboximide (Ref: KBR 2738 M16)

3-hydroxy-fenhexamid

Animal

fenhexamid glucuronide (Ref: KBR 2738 M17)

Rat; Animal

glucuronide of 40hydroxy-fenhexamid (Ref: KBR 2738 M18)

Rat; Animal

succinic acid (Ref: KBR 2738 M26)

Water

N-(3-chloro-4-hydroxyphenol)-1-methyl cyclohexanecarboxamide (Ref: KBR 2738 M13)

3-monochlorofenhexamid

Water

monohydroxychinone fenhexamid (Ref: KBR 2738 M14)

Water

1-methyl-N-(2,3,4-trihydroxyphenyl)cyclohexanecarboximide (Ref: KBR 2738 M15)

trishydroxyphenyl fenhexamid

Water

N-(2,3-dichloro-4-(beta-D-glucopyranosyl-oxy)phenyl)-2-hydroxy-1-methylcyclohexane-carboximde (Ref: KBR 2738 M07)

4-hydroxy-fenhexamid glucoside

Plant

fenhexamide sulfate (Ref: KBR 2738 M27)

Water

N-(2,3-dichloro-4-(beta-D-glucopyranosyl-oxy)phenyl(-1-methylcyclohexane-carboximde) (Ref: KBR 2738 M01)

fenhexamid glucoside

Plant;

N-(2,3-dichloro-4-hydroxyphenyl)-2-hydroxy-1-methyl-cyclohexanecarboximide (Ref: KBR 2738 M03)

2-hydroxy-fenhexamid

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)

Rat 2 yr

(ppm diet)

500

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

1814

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 804.4

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

154

Colinus virginianus

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

> 9.9

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 10 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

207

Apis mellifera

Low

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

> 102.07

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) as % Mortality at dose 4 kg ha⁻¹

< 50.0

Coccinella septempunctata

Beneficial insects (Lacewings)

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

> 4970

Aphidius rhopalosiphi

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

> 4970

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)

1.34

Oncorhynchus mykiss

Moderate

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

0.101

Oncorhynchus mykiss 96 day

Moderate

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

2.52

Danio rerio EC₅₀ Embryo

Moderate

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

> 18.8

Daphnia magna

Moderate

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

> 1.01

Daphnia magna

Moderate

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

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

3.9

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

6.2

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

52.8

Chironomus riparius

Moderate

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

> 1.0

Lemna gibba 14 day

Moderate

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

> 26.1

Scenedesmus subcapitata

Low

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

5.36

Unknown species

Low

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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.06

Rat 4 hr (dust nose only)

Other Mammal toxicity endpoints

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

0.2

Dog 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)

0.2

Dog SF=100

Dermal penetration studies (%)

0.2-8

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No significant risk for proposed uses

Occupational

May be absorbed through skin - PPE required

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

Rapid elimination, >97% absorbed, eliminated mainly in the faeces and to lesser extent in the urine

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 liver, kidney and erthrocytes toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Environment: H411

WHO Classification

U (Unlikely to present an acute hazard)

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

fenhexamid

French

fenhexamid

German

Fenhexamid

Danish

fenhexamid

Italian

fenexamid

Spanish

fenhexamida

Greek

fenhexamid

Polish

fenheksamid

Swedish

fenhexamid

Hungarian

Dutch

fenhexamide

Norwegian

fenheksamid

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