Benzovindiflupyr

Benzovindiflupyr	Last updated: 22/01/2023
(Also known as: Solatenol)

SUMMARY

Benzovindiflupyr is a fungicide active agaist a range of fungal diseases on cereals and other crops. It is not highly soluble in water nor is it volatile. However, depending on local conditions, it can be very persistent in soil and aqueous systems. Risk of leaching to groundwater is low. Its toxicity to biodiverrsity is high to moderate although it is not toxic to honeybees. It is highly toxic to mammals including humans if ingested but little else is known about its potenrtial to harm human health.

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 High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Mammals chronic toxicity: High

GENERAL INFORMATION

Description

A fungicide active agaist a range of fungal diseases on cereals and other crops

Example pests controlled

Apple scab; Botrytis; Anthracnose; Sooty blotch; Fly speck; Powdery mildew; Rust

Example applications

Cereals inc wheat, rye, barley, oats; Corn; Cucurbit and fruiting vegetables; Grapes; Peanuts; Pome fruit; Potatoes; Soybeans; Sugarcane

Efficacy & activity

Efficiacy demonstrated during European field trials

Availability status

Current

Introduction & key dates

2013

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

02/03/2026

UK LERAP status

Crop over 5m DRT - See Authorisation for Crop LERAP Details

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Austria

Date EC 1107/2009 inclusion expires

02/03/2023

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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
✓		✓	✓	✓	✓	✓	✓	✓

Additional information

Also used in

Chemical structure

Isomerism

Substance is racemic.

Chemical formula

C₁₈H₁₅Cl₂F₂N₃O

Canonical SMILES

CN1C=C(C(=N1)C(F)F)C(=O)NC2=CC=CC3=C2C4CCC3C4=C(Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

CCCGEKHKTPTUHJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H15Cl2F2N3O/c1-25-7-11(15(24-25)17(21)22)18(26)23-12-4-2-3-8-9-5-6-10(13(8)12)14(9)16(19)20/h2-4,7,9-10,17H,5-6H2,1H3,(H,23,26)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
benzovindiflupyr	-

General status

Pesticide type

Fungicide

Substance groups

Amide fungicide; Pyrolecarboxamide fungicide

Minimum active substance purity

[EU 2015 dossier: None declared]

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibits mitochondrial functions - Succinate Dehydrogenase Inhibitor (SDHI)

CAS RN

1072957-71-1

EC number

691-719-4

CIPAC number

981

US EPA chemical code

129221

PubChem CID

53491464

CLP index number

616-218-00-X

Molecular mass

398.23

PIN (Preferred Identification Name)

rac-N-[(1R,4S)-9-(dichloromethylidene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide

IUPAC name

N-((1RS,4SR)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide

CAS name

N-(9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide

Other status information

Potential groundwater contaminant

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

Physical state

White powder

Formulations

Property

Value

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

Syngenta

Example products using this active

Aprovia
Trivapro
Elatus
Ascernity
Solatenol

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.98

at 25 °C

Low

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

350000

Acetone

450000

Dichloromethane

190000

Ethyl acetate

76000

Methanol

Melting point (°C)

148.4

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

285

Flashpoint (°C)

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

2.00 X 10⁰⁴

Calculated

Log P

4.3

at 25 °C

High

Fat solubility of residues

Solubility

Insoluble

Data type

Observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

N/a

No dissiciation

Vapour pressure at 20 °C (mPa)

3.2 X 10^-06

Low volatility

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

1.3 X 10^-06

Non-volatile

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

Neutral: 220nm=30539, 249nmj=11864, 295nm=962
Acidic: 220nm=29989, 249nm=11712, 295nm=1008
Basic: 220nm=28442, 249nm=11527, 295nm=1111

Surface tension (mN m⁻¹)

63.0

90% sat soln

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

908

Very persistent

DT₅₀ (lab at 20 °C)

908

Very persistent

DT₅₀ (field)

127.3

Persistent

DT₉₀ (lab at 20 °C)

1000

Very persistent

DT₉₀ (field)

840.5

DT₅₀ modelling endpoint

184

Geometric mean field studies

Note

EU 2015 dossier lab studies DT₅₀ (normalised) range 596-1216 days; DT₉₀ (measured) >1000 days, Soils=6; Field studies DT₅₀ (measured) range 0.001-336 days, DT₉₀ (measured) range 542-840 days, Soils=6

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

44.2

Stable

Note

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

Value

Stable

Note

Stable at all relevant pHs

Water-sediment DT₅₀ (days)

559

Stable

Water phase only DT₅₀ (days)

27.1

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

62.1

Slightly mobile

K_foc

3697

¹/_n

0.91

Notes and range

EU 2015 dossier K_f range 31.6-93.3 mL g⁻¹, K_foc range 3172-4507 mL g⁻¹, ¹/_n range 0.88-0.93, Soils=6

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.91

Calculated

Low leachability

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

Value

1.82 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

123

Threshold for concern

CT₅₀ (days)

0.54

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

desmethyl-benzovindiflupyr (Ref: SYN546206)

Minor fraction

0.056

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (Ref: M700F001)

Major fraction

0.118

N-[(1R,2S,4S)-9-(dichloromethylene)-2-hydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN546040)

Minor fraction

3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN508272)

Minor fraction

N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN546527)

Minor fraction

N-[(1R,2R,4S)-9-(dichloromethylene)-2-hydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN546039; CSCS695908)

Minor fraction

3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN508272)

Minor fraction

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹)

3-(difluoromethyl)-1-methylpyrazole-4-carboxylic acid (Ref: NOA449410; M700F001)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

N-[(1R,2R,4S)-9-(dichloromethylene)-2-hydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN546039)

CSCS695908

Plants; Animal; Hen (eggs)

N-[(1R,2S,4S)-9-(dichloromethylene)-2-hydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (Ref: SYN546040)

Surface water

N-[(1R,2R,4S)-9-(dichloromethylene)-2-hydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1H-pyrazole-4-carboxamide (Ref: SYN546041)

Animal

N-[(1R,2S,4S)-9-(dichloromethylene)-2-hydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1H-pyrazole-4-carboxamide (Ref: SYN546042)

Animal; Hen (eggs)

N-[(1R,3S)-2-(dichloromethylene)-3-hydroxy-1-(2-hydroxyethyl)-2,3-dihydro-1H-inden-4-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Ref: SYN546422)

Animal

3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (Ref: SYN545720)

Plants; Animal

3-(difluoromethyl)-1-methylpyrazole-4-carboxylic acid (Ref: NOA449410)

M700F001

Plant

3-(difluoromethyl)-1H-pyrazole-4-carboxylic (Ref: SYN545720)

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

55.0

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

17.5

Rat

High

(ppm diet)

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

6.8

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

1315

Colinus virginians

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5625 mg kg feed⁻¹

Colinus virginians

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

Anas platyrhynchos NOEC

Moderate

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

203.15

Eisenia foetida corr

Moderate

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

3.91

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 1.37 mg kg⁻¹ soil 28 days

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

47.7

Folsomia candida

Non-target plants

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)

> 109

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 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

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ gt/ha

282.5

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ 6/ha

> 600

Typhlodromus pyri Protonymph

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0035

Cyprinus carpio

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00095

Pimephales promelas

High

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

0.085

Dapnia magna

High

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

0.015

Dapnia magna

Moderate

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

0.056

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)

6.7

Chironomus riparius

Moderate

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

> 0.88

Lemna gibba

Moderate

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

> 0.89

Pseudokirchneriella subcapitata

Moderate

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

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)

55.0

Rat

High

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.56

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.05

Rat SF=100

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

0.1

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)

0.04

Rat SF=100

Dermal penetration studies (%)

1-3%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk for bystanders and residents

Occupational

Low risk with PPE/PPC

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL updated September 2022 for onions and leeks. Consult register.

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapidly eliminated mainly via faeces (84-90%)

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 liver toxicant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive
Not expected to autoignite; Not highly flammable

CLP classification 2013

Health: H301, H331
Environment: H400, H410

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

benzovindiflupyr

French

benzovindiflupyr

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	22/01/2023
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