Binapacryl

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.[1]

Binapacryl[1]
Names
Preferred IUPAC name
2-(Butan-2-yl)-4,6-dinitrophenyl 3-methylbut-2-enoate
Other names
2-[(2RS)-Butan-2-yl]-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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.921
EC Number
  • 207-612-9
KEGG
RTECS number
  • GQ5600000
UNII
UN number 2779
  • 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 checkY
    Key: ZRDUSMYWDRPZRM-UHFFFAOYSA-N checkY
  • 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,5H2,1-4H3
    Key: ZRDUSMYWDRPZRM-UHFFFAOYAH
  • O=C(Oc1c(cc(cc1C(C)CC)[N+]([O-])=O)[N+]([O-])=O)\C=C(/C)C
Properties
C15H18N2O6
Molar mass 322.317 g·mol−1
Density 1.2 g/cm3
Melting point 66 to 67 °C (151 to 153 °F; 339 to 340 K)
Insoluble
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H312, H360, H410
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 [77 °F], 100 kPa).
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Infobox references

International trade in binapacryl is regulated by the Rotterdam Convention; it has been withdrawn as a pesticide, since products were highly toxic to mammals, fish and aquatic invertebrates.[2]

References

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