Dim strFileName() As String
strFileName = IO.File.ReadAllLines(filename, Encoding.GetEncoding(1253))

Dim headerIdent as string = "H" 
 Dim g As Guid
         For Each myLine In strFileName 
                If Not myLine = Chr(endCharacter) Then
                    If myLine.Substring(0, 2) = headerIdent Then

                         g = Guid.NewGuid()

                    End If
                    tempStr &= g & ";" & myLine.ToString & Environment.NewLine    

                End If
            Next

DECLARE @t TABLE (ItemID INT, strcol VARCHAR(100))

INSERT INTO @t
SELECT 222, 'H;123442;23%;78.99;52000990889'
UNION ALL SELECT 222, 'L;socks;blue;100'
UNION ALL SELECT 222, 'L;socks;red;200'
UNION ALL SELECT 223, 'H;123443;23%;500.99;52000990111'
UNION ALL SELECT 223, 'L;skirt;blue;100'
UNION ALL SELECT 223, 'L;pants;red;200'

DECLARE @x TABLE (ItemID INT, xmlcol XML)

;WITH CreateXML AS (
        SELECT ItemID, strcol
            ,xmlcol=CASE SUBSTRING(strcol, 1, 1) 
                        WHEN 'H' THEN '<h>' + STUFF(deliveryPlace + '</deliveryPlace></h>', 1, 1, '')
                        ELSE '<d>' + STUFF(qty + '</qty></d>', 1, 1, '') END
            ,rn=ROW_NUMBER() OVER (PARTITION BY ItemID ORDER BY (SELECT NULL))
        FROM @t
        CROSS APPLY (
            SELECT STUFF(strcol, CHARINDEX(';', strcol), 1, '<inv_number>')) a(inv_number)
        CROSS APPLY (    
            SELECT STUFF(inv_number, CHARINDEX(';', inv_number), 1, '</inv_number><vat>')) b(vat)
        CROSS APPLY (    
            SELECT STUFF(vat, CHARINDEX(';', vat), 1, '</vat><amount>')) c(amount)
        CROSS APPLY (    
            SELECT STUFF(amount, CHARINDEX(';', amount), 1, '</amount><deliveryPlace>')) d(deliveryPlace)
        CROSS APPLY (    
            SELECT STUFF(strcol, CHARINDEX(';', strcol), 1, '<itemDescription>')) e(itemDescription)
        CROSS APPLY (    
            SELECT STUFF(itemDescription, CHARINDEX(';', itemDescription), 1, '</itemDescription><color>')) f(color)
        CROSS APPLY (    
            SELECT STUFF(color, CHARINDEX(';', color), 1, '</color><qty>')) g(qty)
        ),
    CreateXML2 AS (
        SELECT ItemID
            ,xmlcol=CAST((
                SELECT CASE WHEN SUBSTRING(xmlcol, 2, 1) = 'h' THEN '<ItemID>' + CAST(ItemID AS VARCHAR(5)) + '</ItemID> ' ELSE '' END + 
                    xmlcol
                FROM CreateXML b 
                WHERE a.ItemID = b.ItemID
                ORDER BY rn
                FOR XML PATH(''), TYPE).value('.', 'VARCHAR(MAX)') AS XML)
        FROM CreateXML a
        GROUP BY ItemID
        )
INSERT INTO @x
SELECT ItemID, xmlcol
FROM CreateXML2 

-- Extract headers
SELECT x.row.value('(.)[1]', 'INT') AS ItemID
	,x.row.value('(/h/inv_number)[1]', 'VARCHAR(50)') AS inv_number
	,x.row.value('(/h/vat)[1]', 'VARCHAR(50)') AS vat
	,x.row.value('(/h/amount)[1]', 'MONEY') AS amount
	,x.row.value('(/h/deliveryPlace)[1]', 'VARCHAR(50)') AS deliveryPlace
FROM @x
CROSS APPLY xmlcol.nodes('/ItemID') AS x(row)

-- Extract details
SELECT y.row.value('(.)[1]', 'VARCHAR(50)') AS ItemID
	,x.row.value('(/h/inv_number)[1]', 'VARCHAR(50)') AS inv_number
	,x.row.value('(./itemDescription)[1]', 'VARCHAR(50)') AS itemDescription
	,x.row.value('(./color)[1]', 'VARCHAR(50)') AS color
	,x.row.value('(./qty)[1]', 'INT') AS qty
FROM @x
CROSS APPLY xmlcol.nodes('/d') AS x(row)
CROSS APPLY xmlcol.nodes('/ItemID') AS y(row)