Public Class Form1
 
  Private Sub Form1_Load(sender As Object, e As EventArgs) Handles MyBase.Load
 
    For i As Integer = 1 To 6
      Dim ausgewählt As Boolean = (i Mod 3 = 0)
      Dim menuItem = New ToolStripMenuItem("Element " & i) With {.Checked = ausgewählt}
      AddHandler menuItem.CheckedChanged, AddressOf ToolStripMenuItem_CheckedChanged
      TestweiseToolStripMenuItem.DropDownItems.Add(menuItem)
    Next
  End Sub
 
  Private Sub ToolStripMenuItem_CheckedChanged(sender As Object, e As EventArgs)
    Dim menuItem = CType(sender, ToolStripMenuItem)
    MessageBox.Show("Menüeintrag """ & menuItem.Text & """ wurde verändert. Ist nun " & menuItem.Checked)
  End Sub
 
End Class