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Binapacryl (Ref: FMC 9044)
(Also known as: endosan; HOE 02784; OMS 571)
SUMMARY
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.
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:
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
-
Availability status
Considered obsolete - banned or voluntarily withdrawn - but may be available in some countries
Introduction & key dates
circa 1960
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
UK LERAP status
No UK approval for use
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
A racemate comprising equimolar amounts of (R)- and (S)-binapacry
Chemical formula
C₁₅H₁₈N₂O₆
Canonical SMILES
CCC(C)C1=CC(=CC(=C1OC(=O)C=C(C)C)[N+](=O)[O-])[N+](=O)[O-]
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
ZRDUSMYWDRPZRM-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C15H18N2O6/c1-5-10(4)12-7-11(16(19)20)8-13(17(21)22)15(12)23-14(18)6-9(2)3/h6-8,10H,5H2,1-4H3
2D structure diagram/image available?
Yes
General status
Pesticide type
Fungicide, Insecticide, Miticide, Acaricide
Substance groups
Dinitrophenol acaricide; Dinitrophenol insecticide; Dinitrophenol fungicide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic. As a miticide it works with ovicidal action, uncoupling or inhibiting oxidative phosphorylation. Respiration inhibitor.
CAS RN
485-31-4
EC number
207-612-9
CIPAC number
138
US EPA chemical code
012201
PubChem CID
10234
CLP index number
609-024-00-1
Molecular mass
322.31
PIN (Preferred Identification Name)
rac-2-[(2R)-butan-2-yl]-4,6-dinitrophenyl 3-methylbut-2-enoate
IUPAC name
(RS)-2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate
CAS name
2-(1-methylpropyl)-4,6-dinitrophenyl 3-methyl-2-butenoate
Other status information
Chemical subject to PIC regulations; Severe Marine Pollutant; Rotterdam Convention (Class O)
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
13
Fungicide Resistance Classification (FRAC)
29
Examples of recorded resistance
Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus mcdanieli
Physical state
Colourless to yellow or brownish crystalline powder
Formulations
Property
Value
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 poweders
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
Hexane		 -
Melting point (°C)
67
A4 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 )
4 = Verified data
 -
Boiling point (°C)
Decomposes before boiling
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
P
5.62 X 1004 Calculated -
Log P
4.75
A4 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 )
4 = Verified data
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.24
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
13
A4 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 )
4 = Verified data
at 60°C		 Highly volatile
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
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 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
-
V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
1 = Estimated data with little or no verification
 Slightly mobile
Koc
2400
Notes and range
Estimated
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
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 -
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
Calculated		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
dinoseb (Ref: HOE 26150) - Mammal (dog) - -
3-(2-hydroxy-3,5-dinitrophenyl)-butanol - Mammal (dog) - -
3-(2-hydroxy-3,5-dinitrophenyl)-butyric acid - Mammal (dog) - -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
58
F4 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 )
4 = Verified data
Rat		 High
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)
> 800
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
- - -
- - -
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
- - -
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
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
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.03
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
Asellus brevicaudus 		High
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)
10.8
F4 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 )
4 = Verified data
Scenedesmus subspicatus		 Low
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)
58
F4 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 )
4 = Verified data
Rat		 High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
720
F4 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 )
4 = Verified data
Rat		 -
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
-
Occupational
The probable routes of exposure to binapacryl are by dermal contact or inhalation of dust
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
?Possibly, status not identified
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E2 E = Unspecified genotoxicity type (miscellaneous data source)
2 = Mixed/ambiguous results
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
✓Yes, known to cause a problem
XNo, known not to cause a problem
?Possibly, status not identified
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
✓Yes, known to cause a problem
 No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
 No data found  
General human health issues
Highly toxic and may damage liver, kidneys and nervous system
Shows teratogenicity
Handling issues
Property
Value and interpretation
General
Avoid generation of dust
It is readily hydrolized by strong acids or dilute alkalis
CLP classification 2013
Health: H302, H312, H360D
Environment: H400, H410
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
binapacryl
French
binapacryl
German
Binapacryl
Danish
binapacryl
Italian
binapacril
Spanish
binapacril
Greek
binapacryl
Polish
binapakryl
Swedish
-
Hungarian
-
Dutch
binapacryl
Norwegian
-
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