Bispyribac	Last updated: 22/01/2023
(Not known by any other names)

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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
		Human health Low alert

GENERAL INFORMATION

Description	A post-emergence herbicide, usually used as the sodium salt, for the control of grasses, sedges and broad-leaved weeds in paddy rice and other crops/situations
Example pests controlled	Alligatorweed, Duckweed, Mosquito ferm, Water fern, Water hyacinth, Water pennywort, Parrot feather; Annual bluegrass; Creeping bent grass
Example applications	Aquatic sitiuations such as drainage ditches, lakes, marshes; Golf courses, turf grass & sod farms
Efficacy & activity	-
Availability status	Current
Introduction & key dates	1998, discovered; 1997, first introduced

UK regulatory status

UK COPR regulatory status	Approved
Date COPR inclusion expires	31/07/2026
UK LERAP status	No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Approved
Dossier rapporteur/co-rapporteur	Italy/Portugal
Date EC 1107/2009 inclusion expires	31/07/2023
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes - as sodium salt
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	None
Chemical formula	C₁₉H₁₈N₄O₈
Canonical SMILES	COC1=CC(=NC(=N1)OC2=C(C(=CC=C2)OC3=NC(=CC(=N3)OC)OC)C(=O)O)OC
Isomeric SMILES	-
International Chemical Identifier key (InChIKey)	RYVIXQCRCQLFCM-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C19H18N4O8/c1-26-12-8-13(27-2)21-18(20-12)30-10-6-5-7-11(16(10)17(24)25)31-19-22-14(28-3)9-15(23-19)29-4/h5-9H,1-4H3,(H,24,25)
2D structure diagram/image available?	Yes

General status

Pesticide type	Herbicide
Substance groups	Pyrimidinyl carboxy compound; Benzoic acid herbicide
Minimum active substance purity	-
Known relevant impurities	EU dossier - none identified
Substance origin	Synthetic
Mode of action	Selective, systemic action absorbed by foliage and roots.Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.
CAS RN	125401-75-4
EC number	603-065-9
CIPAC number	748
US EPA chemical code	-
PubChem CID	443031
CLP index number	No data found
Molecular mass	430.37
PIN (Preferred Identification Name)	2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid
IUPAC name	2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid
CAS name	2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoic acid
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	B
Herbicide Resistance Classification (WSSA)	2
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Resistance to ALS-inhibitors is locally present in sub-populations of Alisma plantago-aquatica and Schoenoplectus mucronatus in Southern European rice growing areas
Physical state	-
Related substances & organisms	bispyribac-sodium pyriflubenzoxim

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Kumiai Chemical Industry
Example products using this active	Adora 400 SC Nominee 400 SC Tradewind
Formulation and application details	Usually supplied as a suspension concentrate that is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		-	-	-
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		-	-	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	-	-	-
	Log P	-	-	-
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		-	-	-
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT₅₀ (typical)	-	-	-
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	-
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	-	-	-
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	-	-	-
	Note	-
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		-	-	-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	Cannot be calculated	-	-
	Note	-
Potential for particle bound transport index		-	-	-
Potential for loss via drain flow		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
benzoic acid, 2-((4,6-dimethoxy-2-pyrimidinyl)oxy)6-hydroxy, sodium salt	Major fraction	-	-
benzoic acid, 2-(4,6-dimethoxy-2-pyrimidinyl)oxy)-6-((4-hydroxy-6-methoxy-2-pyrimidinyl)oxy), sodium salt (Ref: KIB 8651)	Major fraction	-	-
2,4-dihydroxy-6-methoxypyrimidine	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)
2,4-dihydroxy-6-methoxypyrimidine	Relevancy unknown	-	-
benzoic acid, 2-((4,6-dimethoxy-2-pyrimidinyl)oxy)6-hydroxy, sodium salt	Relevancy unknown	-	-
benzoic acid, 2-(4,6-dimethoxy-2-pyrimidinyl)oxy)-6-((4-hydroxy-6-methoxy-2-pyrimidinyl)oxy), sodium salt (Ref: KIB 8651)	Relevancy unknown	-	-

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		-	-	-
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	-	-
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		-	-	-
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		-	-	-
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		-	-	-
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)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	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)		-	-	-
Beneficial insects (Lacewings)		-	-	-
Beneficial insects (Parasitic wasps)		-	-	-
Beneficial insects (Predatory mites)		-	-	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
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)		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		-	-	-
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	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)		-	-	-
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		-	-	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		-	-	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Routes	Public	Risks acceptable for proposed uses
	Occupational	Risks acceptable for proposed uses
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 XNo, known not to cause a problem A3 A = Chromosome aberration (EFSA database) 3 = Negative ; B3 B = DNA damage/repair (EFSA database) 3 = Negative ; C3 C = Gene mutation (EFSA database) 3 = Negative ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant XNo, known not to cause a problem XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser No data found ?Possibly, status not identified ✓Yes, known to cause a problem Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		Possible liver toxicant

Handling issues

Property	Value and interpretation
General	Not explosive Not expected to autoignite; Not highly flammable
CLP classification 2013	Health: H317, H319 Environment: H411
WHO Classification	III (Slightly hazardous)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	bispyribac
French	bispyribac
German	Bispyribac
Danish	bispyribac
Italian	bispyribac
Spanish	bispiribac
Greek	-
Polish	bispirybak
Swedish	-
Hungarian	-
Dutch	-

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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