Benthiavalicarb isopropyl (Ref: KIF-230)

Benthiavalicarb isopropyl (Ref: KIF-230)	Last updated: 12/01/2021
(Also known as: benthiavalicarb; HSDB 7501)

SUMMARY

Benthiavalicarb isopropyl is a fungicide approved for use in the EU. It has a low aqueous solubility, volatile and presents a moderate risk of leaching to groundwater. It is not expected to persist in soils but could persist in aquesous systems under some conditions. It has a low mammalian oral toxicity, may cause adverse reproduction/fertility effects and may also be carcinogenic. Benthiavalicarb isopropyl is moderately toxic to fish, aquatic invertebrates, algae, earthworms and honey bees.

GENERAL INFORMATION

Description

A new fungicide active against Oomycetes fungal plant pathogens

Example pests controlled

Blight; Downy mildew

Example applications

Potatoes; Vines; Tomatoes; Grapes

Efficacy & activity

Efficiacy demonstrated via extensive use and field trials

Availability status

Current

Introduction & key dates

2003

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Poland/France

Date EC 1107/2009 inclusion expires

31/07/2021

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

Chemical structure

Isomerism

Benthiavaliarb-isopropyl is a mixture of R-L and S-L stereoisomers. The R-L stereoisomer is the main pesticidally active component. The S-L stereoisomer is not pesticidally-active an is present as a minor impurity.

Chemical formula

C₁₈H₂₄FN₃O₃S

Canonical SMILES

CC(C)C(C(=O)NC(C)C1=NC2=C(S1)C=C(C=C2)F)NC(=O)OC(C)C

Isomeric SMILES

C[C@H](C1=NC2=C(S1)C=C(C=C2)F)NC(=O)[C@H](C(C)C)NC(=O)OC(C)C

International Chemical Identifier key (InChIKey)

USRKFGIXLGKMKU-ABAIWWIYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H24FN3O3S/c1-9(2)15(22-18(24)25-10(3)4)16(23)20-11(5)17-21-13-7-6-12(19)8-14(13)26-17/h6-11,15H,1-5H3,(H,20,23)(H,22,24)/t11-,15-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Carbamate

Minimum active substance purity

910 g kg⁻¹

Known relevant impurities

EU dossier - 6,6’-difluoro-2,2’-dibenzothiazole <3.5 mg kg⁻¹, bis(2-amino-5-fluorophenyl)disulphide 14 mg kg⁻¹, toluene - 5 g kg⁻¹

Substance origin

Synthetic

Mode of action

Protective and curative action with residual effects, inhibits phospholipid biosynthesis

CAS RN

177406-68-7

EC number

CIPAC number

744.204

US EPA chemical code

098379

PubChem CID

53297381

Molecular mass

381.47

PIN (Preferred Identification Name)

IUPAC name

isopropyl [(S)-1-{[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]carbamoyl}-2-methylpropyl]carbamate

CAS name

1-methylethyl N-[(1S)-1-[[[(1R)-1-(6-fluoro-2-benzothiazolyl)ethyl]amino]carbonyl]-2-methylpropyl]carbamate

Other status information

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

Related substances & organisms

mancozeb

benthiavalicarb

Formulations

Property

Value

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

Valbon

Example products using this active

Certis
Kumiai Chemical Co

Formulation and application details

Usually supplied as dispersible granules that are used as an aqueous spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

13.1

Low

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

501

Xylene

25400

Acetone

11500

1,2-Dichloromethane

19400

Ethyl acetate

Melting point (°C)

153.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

240

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.63 X 10⁰²

Calculated

Log P

2.56

Low

Bulk density (g ml⁻¹)

1.25

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.3

Low volatility

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

4.53 X 10^-03

Non-volatile

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

Neutral solution: 219nm = 24424, 292.5nm = 1298
Acidic soln: 219nm=23891
Basic soln: 220.5nm=23075

Surface tension (mN m⁻¹)

63.1

at 22°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

13.8

Non-persistent

DT₅₀ (lab at 20 °C)

13.8

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

54.0

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2016 dossier lab studies DT₅₀ range 10.6-18.8 days, DT₉₀ range 35.3-72.7 days, Soils=4

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

516

Stable

Note

DT₅₀ 6.8 days at pH 5, 178 days at pH 9

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

Value

Stable

see also R4

Stable

Note

Stable at pH 4 to 9 up to 50 °C

Water-sediment DT₅₀ (days)

16.6

Fast

Water phase only DT₅₀ (days)

6.05

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

6.28

Moderately mobile

K_oc

245.2

Notes and range

EU 2016 dossier K_d range 0.85-9.5 mL g⁻¹, K_oc range 166.6-379.5 mL g⁻¹, Soils=4

Freundlich

K_f

4.06

Moderately mobile

K_foc

180.6

¹/_n

0.88

Notes and range

EU 2016 dossier kf range 0.8-0.65 mL g⁻¹, K_foc range 121.3-258.2 mL g⁻¹, ¹/_n range 0.84-0.93, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.99

Calculated

Transition state

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^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

6-fluoro-2-hydroxybenzothiazole (Ref: KIF-230-M1)

Soil

0.277

Major fraction, Relevant

1-(6-fluoro-2-benzothiazol-2-yl)ethanol (Ref: KIF-230-M3)

Soil

0.123

Major fraction, Relevant

1-(6-fluoro-2-benzothiazolyl)ethylamine (Ref: KIF-230-M5)

Soil

0.268

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

6-fluorobenzothiazol-2-yl methyl ketone

KIF-230-M4

Soil

N-[1-(6-Fluorobenzothiazol-2-yl)ethyl]acetamide

KIF-230-M8

Soil (Anaerobic)

6,6’-difluoro-2,2’-dibenzothiazole
Note: IMPURITY

KF-230-I-6

IMPURITY

n/a

bis(2-amino-5-fluorophenyl) disulfide
Note: IMPURITY

KF-230-I-12

IMPURITY

n/a

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 14

Rat

High

(ppm diet)

> 200

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

702

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 937 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

105

Colinius virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 10

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

1.0

Oncorhynchus mykiss 28 day

Moderate

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

> 10

Daphnia magna

Moderate

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

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

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

> 10

Pseudokirchneriella subcapitata

Low

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)

> 100

Apis mellifera

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)

> 148.1

Bombus terrestris

Low

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

> 740.5

Bombus terrestris

Low

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)

162.0

Eisenia foetida corr

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

6000

48 hour, reproduction
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

290

7 day, reproduction
Typhlodromus pyri adult

% Effect

Soil micro-organisms

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

Dose: 2.65 mg kg⁻¹ soil

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.6

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.1

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)

None allocated

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

5.0

Rat SF=100

Dermal penetration studies (%)

16-70

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Protective clothing should be worn
Possible risk from dermal exposure

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

May cause allergic reaction
Possible liver & thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317, H319, H332, H351
Environment: H400

EC Risk Classification

Carcinogen category 3: R40
N - Dangerous for the environment: R52, R53

EC Safety Classification

S36/37, S61

WHO Classification

NL (Not listed)

UN Number

Active 2757, liquid products usually 2992

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

benthiavalicarb isopropyl

French

German

Danish

Italian

bentiavalicarb isopropil

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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