| binapacryl (Ref: FMC 9044) |
 |
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SUMMARY
Binapacryl is a fungicide not approved for use in the EU. 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. GENERAL INFORMATION 
for binapacryl
Description: An obsolete contact fungicide and acaricide once used to control mildew and mites on certain fruits and vegetables
Example pests controlled: Powdery mildew; Panonychid and Tetranychid mites
Example applications: Apples; Pears; Cucumber
Efficacy & activity: -
Availability status: Obsolete
Introduction & key dates: circa 1960
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Not applicable |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | - |
| 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 |
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Chemical structure:
| Isomerism | - |
| Chemical formula | C15H18N2O6 |
| Canonical SMILES | CCC(C)C1=CC(=CC(=C1OC(=O)C=C(C)C)[N+](=O)[O-])[N+](=O)[O-] |
| Isomeric SMILES | No data |
| 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 |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide, Insecticide, Miticide | |
| Substance group | Dinitrophenol | |
| 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 (g mol-1) | 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) | Not known | |
| Fungicide Resistance Classification (FRAC) | 29 | |
| Examples of recorded resistance | Panonychus citri Panonychus ulmi Tetranychus urticae Tetranychus mcdanieli |
|
| Physical state | Colourless to brownish crystalline powder | |
| Related substances & organisms | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Formulated as emulsifiable concentrates and wettable poweders. | |||
ENVIRONMENTAL FATE
for binapacryl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 1 | Q2 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 780000 | R3 - Acetone | - | |
| 110000 | R3 - Ethanol | - | ||
| 700000 | R3 - Xylene | - | ||
| 400 | L3 - Hexane | - | ||
| Melting point (oC) | 67 | A4 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 5.62 X 1004 | Calculated | - |
| Log P | 4.75 | A4 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.24 | Q2 | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 13 | A4 | Highly volatile | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 0.034 | CA3 | Non-volatile | |
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 |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 100 | F3 | Persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| 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 20oC and pH 7 | Value | - | - | - |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | CA2 | Slightly mobile |
| Koc | 2400 | |||
| Notes and range | Estimated | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 2400 | F3 Calculated | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 58 | F4 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 800 | V2 Gallus gallus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 0.05 | F3 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.03 | F3 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) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 10.8 | F4 Scenedesmus subspicatus | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 50 | F3 | Moderate |
| Oral acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | - | - | - | |
| 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 | - | - | - |
| % Effect | Moderately harmful | AB1 Typhlodromus pyri | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for binapacryl
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) | 58 | F4 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 720 | F4 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | - | - | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.002 | F3 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | - | - | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | The probable routes of exposure to binapacryl are by dermal contact or inhalation of dust | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Highly toxic and may damage liver, kidneys and nervous system Shows teratogenicity |
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: 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 |
Avoid generation of dust Hazard class 6.1 |
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| CLP classification 2013 | Health: H302, H312, H360D Environment: H400, H410 |
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| EC Risk Classification |
Reproduction risk category 2: R61 Xn - Harmful: R21/22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S45, S53, S61, S60 | |||
| WHO Classification | O | - | Obsolete substance | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | - | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | binapacryl |
| French | binapacryl |
| German | Binapacryl |
| Danish | binapacryl |
| Italian | binapacril |
| Spanish | binapacril |
| Greek | binapacryl |
| Slovenian | binapakril |
| Polish | binapakryl |
| Swedish | - |
| Hungarian | - |
| Dutch | binapacryl |
Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk