benthiavalicarb isopropyl (Ref: KIF-230) ** benthiavalicarb ** HSDB 7501 ** Translations

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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
for benthiavalicarb isopropyl

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

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	Poland/France
Date inclusion expires	31/07/2019
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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
Structure diagram/image available?	Yes

General status:

Pesticide type	Fungicide
Substance group	Carbamate
Minimum active substance purity	910 g/kg
Known relevant impurities	EU dossier - 6,6’-difluoro-2,2’-dibenzothiazole <3.5 mg/kg, bis(2-amino-5-fluorophenyl)disulphide 14 mg/kg, toluene - 5 g/kg
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 (g mol-1)	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)	40
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	Certis Kumiai Chemical Co
Example products using this active	Valbon
UK LERAP status	Buffer probably required in UK - see product label
Formulation and application details	Usually supplied as dispersible granules that are used as an aqueous spray.

ENVIRONMENTAL FATE
for benthiavalicarb isopropyl

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		13.1	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		501	A5 - Xylene	-
		25400	A5 - Acetone	-
		11500	A5 - 1,2-Dichloromethane	-
		19400	A5 - Ethyl acetate	-
Melting point (oC)		153.1	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		240	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	3.63 X 1002	Calculated	-
	Log P	2.56	A5	Low
Bulk density (g ml-1)/Specific gravity		1.25	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		0.3	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		4.53 X 10-03	A5	Non-volatile
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		-	Calculated	Low
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	A5	-
Surface tension (mN m-1)		63.1	A5 at 22oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		Not readily biodegradable
Soil degradation (days) (aerobic)	DT50 (typical)	13.8	A5	Non-persistent
	DT50 (lab at 20oC)	13.8	A5	Non-persistent
	DT50 (field)	-	-	-
	DT90 (lab at 20oC)	54.0	A5	-
	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	A5	Stable
	Note	DT50 6.8 days at pH 5, 178 days at pH 9
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5 - see also R4	-
	Note	Stable at pH 4 to 9 up to 50 degC
Water-sediment DT50 (days)		16.6	A5	Fast
Water phase only DT50 (days)		6.05	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	6.28	A5	Moderately mobile
	Koc	245.2
	Notes and range	EU 2016 dossier Kd range 0.85-9.5 mL/g, Koc range 166.6-379.5 mL/g, Soils=4
Freundlich	Kf	4.06	A5	Moderately mobile
	Kfoc	180.6
	1/n	0.88
	Notes and range	EU 2016 dossier kf range 0.8-0.65 mL/g, Kfoc range 121.3-258.2 mL/g, 1/n range 0.84-0.93, Soils=5
pH sensitivity		No

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
for benthiavalicarb isopropyl

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	Low risk	A5 Based on LogP < 3	Low potential
	CT50 (days)	-		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	> 14	A5 Rat	High
	(ppm diet)	> 200		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 937 mg kg bw-1 day-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		> 10	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		1.0	A5 Oncorhynchus mykiss, 28d	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 10	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		3	A5 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	A5 Pseudokirchneriella subcapitata	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 100	A5 Apis mellifera	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 100	A5 Apis mellifera	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 500	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	6000	48 hour, reproduction A5 Aphidius rhopalosiphi, adult	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	290	7 day, reproduction A5 Typhlodromus pyri, adult	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 2.65 mg kg-1 soil	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for benthiavalicarb isopropyl

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 4.6	A5 Rat, 4 hr (whole body)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.1	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		None allocated	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		5.0	A5 Rat, SF=100	-
Dermal penetration studies (%)		16-70	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks to bystanders identified
	Occupational	Protective clothing should be worn Possible risk from dermal exposure
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		0.1	EU Dir 89/778/EC limit; A5	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
				-
General human health issues		May cause allergic reaction Possible liver & thyroid toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising
CLP classification 2013		Health: H317, H351
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
US EPA Classification (formulation)		No consensus across products or no products available	-	-
UN Number		Active 2757, liquid products usually 2992
Waste disposal & packaging		-

TRANSLATIONS
for benthiavalicarb isopropyl

Language	Name
English	benthiavalicarb isopropyl
French	-
German	-
Danish	-
Italian	bentiavalicarb isopropil
Spanish	-
Greek	-
Slovenian	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-

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Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk