Binapacryl is a fungicide. It has a low aqueous solubility, is highly volatile and would not normally be expected to leach to groundwater. Binapacryl may be persistent in soil systems. It is highly toxic to mammals, may cause adverse development/fertility effects and is a known skin irritant. Binapacryl is highly toxic to fish and aquatic invertebrates and moderately toxic to birds and honeybees.
Hazard 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. These hazard alerts do not take account of usage patterns or exposure, thus do not represent risk.
Environmental fate
Ecotoxicity
Human health
Environmental fate High alert: Potential for particle bound transport: High
Warning: Significant data are missing
Ecotoxicity High alert: Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High
Human health High alert: Mammals acute toxicity: High; Reproduction/development effects
GENERAL INFORMATION
Description
An obsolete contact fungicide and acaricide once used to control mildew and mites on certain fruits and vegetables. An ester of dinoseb.
Example pests controlled
Powdery mildew; Panonychid and Tetranychid mites
Example applications
Apples; Pears; Cucumber
Efficacy & activity
-
GB regulatory status
GB COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
GB LERAP status
No UK approval for use as a plant protection agent
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Expired
EU Candidate for substitution (CfS)
No applicable
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
-
Chemical structure
Isomerism
Binapacryl exhibits optical isomerism due to the presence of a chiral centre in its molecular structure. It exists as a racemic mixture, containing equal amounts of the two enantiomers: (R)-binapacryl and (S)-binapacryl.
Colourless to yellow or brownish crystalline powder
Commercial
Property
Value
Availability status
Considered obsolete - banned or voluntarily withdrawn - but may be available in some countries
Introduction & key dates
circa 1960, introduced
Example manufacturers & suppliers of products using this active now or historically
FMC Corp
Hoechst
Example products using this active
Acricid
Ambox
Morocide
Endosan
Dinapacryl
Niagara 9044
Formulation and application details
Formulated as emulsifiable concentrates and wettable powders
Commercial production
The production of binapacryl involves a solvent-based dehydration and crystallisation process designed to minimise impurities and fire hazards. Initially, a wet product of binapacryl is mixed with an organic solvent and subjected to distillation and dehydration. This is followed by continuous dehydration using spray heating or membrane evaporator heating, which also facilitates wet-process smashing, blending, and packaging. In the final step, maneb and zinc are complexed in the solvent while simultaneously dehydrating to induce crystal transformation.
Impact on climate of production and use
Data for the amount of life cycle GHGs produced by binapacryl are not available in the public domain. However, whilst estimates vary, more general data suggests that between 14 and 30 kilograms of CO₂e is emitted per kilogram of pesticide produced.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
1
Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
780000
R3 R = Peer reviewed scientific publications 3 = Unverified data of known source
Acetone
-
110000
R3 R = Peer reviewed scientific publications 3 = Unverified data of known source
Ethanol
-
700000
R3 R = Peer reviewed scientific publications 3 = Unverified data of known source
Xylene
-
400
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes
-
Degradation point (°C)
-
-
-
Flashpoint (°C)
-
-
-
Octanol-water partition coefficient at pH 7, 20 °C
Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
0.034
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source
Non-volatile
Volatilisation as max % of applied dose lost
From plant surface
-
-
-
From soil surface
-
-
-
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)
100
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source
Persistent
DT₅₀ (lab at 20 °C)
-
-
-
DT₅₀ (field)
-
-
-
DT₉₀ (lab at 20 °C)
-
-
-
DT₉₀ (field)
-
-
-
DT₅₀ modelling endpoint
-
-
-
Note
General literature states that it may undergo slow hydrolysis
Dissipation rate RL₅₀ (days) on plant matrix
Value
-
-
-
Note
-
Dissipation rate RL₅₀ (days) 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)
-
-
-
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
Kd (mL g⁻¹)
-
V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 1 = Estimated data with little or no verification
Slightly mobile
Koc (mL g⁻¹)
2400
Notes and range
Estimated
Freundlich
Kf (mL g⁻¹)
-
-
-
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
1.24
Calculated
Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
2.86 X 10-02
Calculated
-
Note
-
Potential for particle bound transport index
High
Calculated
-
Potential for loss via drain flow
Slightly mobile
Calculated
-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
-
-
-
Bio-concentration factor
BCF (l kg⁻¹)
2400
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source
V2 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 2 = Unverified data of unknown source
Gallus domesticus
Moderate
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
Vegetative vigour ER₅₀ (g ha⁻¹)
-
-
-
Seedling emergence ER₅₀ (g ha⁻¹)
-
-
-
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
> 50
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source
Moderate
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
-
-
-
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)
-
-
-
Beneficial insects (Lacewings)
-
-
-
Beneficial insects (Parasitic wasps)
-
-
-
Beneficial insects (Predatory mites)
Moderately harmful
Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source
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)
> 0.05
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source
Oncorhynchus mykiss
High
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
-
-
-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source
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
Environmental fate
Warning:
