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Binapacryl

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Binapacryl
Names
Preferred IUPAC name 2-(Butan-2-yl)-4,6-dinitrophenyl 3-methylbut-2-enoate
Other names 2--4,6-dinitrophenyl 3-methylbut-2-enoate
(RS)-2-(Butan-2-yl)-4,6-dinitrophenyl 3-methylbut-2-enoate
(RS)-2-sec-Butyl-4,6-dinitrophenyl 3-methylbut-2-enoate
Dapacryl
Morocide
Morrocid
Acricid
Endosan
Ambox
Dinoseb methacrylate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.921 Edit this at Wikidata
EC Number
  • 207-612-9
KEGG
PubChem CID
RTECS number
  • GQ5600000
UNII
UN number 2779
CompTox Dashboard (EPA)
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,5H2,1-4H3Key: ZRDUSMYWDRPZRM-UHFFFAOYSA-N
  • InChI=1/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,5H2,1-4H3Key: ZRDUSMYWDRPZRM-UHFFFAOYAH
SMILES
  • O=C(Oc1c(cc(cc1C(C)CC)()=O)()=O)\C=C(/C)C
Properties
Chemical formula C15H18N2O6
Molar mass 322.317 g·mol
Density 1.2 g/cm
Melting point 66 to 67 °C (151 to 153 °F; 339 to 340 K)
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H302, H312, H360, H410
Precautionary statements P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P308+P313, P312, P322, P330, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Binapacryl was used as a miticide and fungicide. Chemically, it is an ester derivative of dinoseb. Although binapacryl has low toxicity itself, it is readily metabolized to form dinoseb, which is highly toxic.

International trade in binapacryl is regulated by the Rotterdam Convention; it has been withdrawn as a pesticide, since products were highly toxic to mammals, fish and aquatic invertebrates.

References

  1. ^ Datasheet from International Programme on Chemical Safety
  2. Pesticide Properties DataBase: Binapacryl
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