| Identification | Back Directory | [Name]
PINOXADEN | [CAS]
243973-20-8 | [Synonyms]
axial
PINOXADEN
pinoxaden 96%
Pinoxaden Solution, 100ppm
Pinoxaden Solution, 1000ppm
Pinoxaden@100 μg/mL in Acetonitrile
Pinoxaden@1000 μg/mL in Acetonitrile
Pinoxaden Solution in Methanol, 100μg/mL
Propanoic acid, 2,2-dimethyl-, 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo1,2-d1,4,5oxadiazepin-9-yl ester | [Molecular Formula]
C23H32N2O4 | [MDL Number]
MFCD08690563 | [MOL File]
243973-20-8.mol | [Molecular Weight]
400.516 |
| Chemical Properties | Back Directory | [Boiling point ]
521.3±60.0 °C(Predicted) | [density ]
1.17±0.1 g/cm3(Predicted) | [pka]
-2.96±0.60(Predicted) | [Henry's Law Constant]
1.1×106 mol/(m3Pa) at 25℃, HSDB (2015) | [Major Application]
agriculture
environmental | [InChI]
InChI=1S/C23H32N2O4/c1-7-16-13-15(3)14-17(8-2)18(16)19-20(26)24-9-11-28-12-10-25(24)21(19)29-22(27)23(4,5)6/h13-14H,7-12H2,1-6H3 | [InChIKey]
MGOHCFMYLBAPRN-UHFFFAOYSA-N | [SMILES]
C(OC1N2N(C(=O)C=1C1=C(CC)C=C(C)C=C1CC)CCOCC2)(=O)C(C)(C)C | [LogP]
4.110 (est) | [EPA Substance Registry System]
Propanoic acid, 2,2-dimethyl-, 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl ester (243973-20-8) |
| Hazard Information | Back Directory | [Uses]
Pinoxaden is derived from Diethylene Glycol Dimethanesulfonate (D444275), which is an intermediate in the production of alkylating agents. | [Definition]
ChEBI: An organic heterobicyclic compound with herbicidal activity. | [Production Methods]
The industrial synthesis of pinoxaden begins with the transformation of 2,6-diethyl-4-methylaniline into 2,6-diethyl-4-methylbromobenzene via a Sandmeyer reaction. This intermediate is then coupled with malononitrile under cuprous iodide catalysis to form 2,6-diethyl-4-methylphenylmalononitrile, which is hydrolysed using hydrogen peroxide in alkaline conditions to yield the corresponding malonamide. The malonamide is reacted with oxadiazepine dihydrobromide in the presence of triethylamine to form the fused heterocyclic core. Finally, pivaloyl chloride is used to esterify the molecule, producing pinoxaden. | [Mechanism of action]
Systemic. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation. | [Pesticide Type]
Herbicide |
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