Abstract
Cyclic hydroxamic acids like 2,4-dihydroxy-7-methoxy-2H-1 ,4-benzoxazin-3(4H)-one (DIM BOA) and 2,4-dihydroxy-2H-1 ,4-benzoxazin-3(4H)-one (DIBOA) are found in several plants playing an important role in the defense-system of plants against a variety of enemies. To investigate new mechanism and effects we synthesized the molecules using known synthetic pathways. Since the chemical data of DIMBOA are not complete or even false, we decided to publish the missing ones in this journal.
Highlights
Benzoxazinoids are naturally occuring in a variety of plants like Secale cereale L. [I], Triticum aestivum L. or Zea mays L. [2] and especially in many important crop plants of the family Gramineae
The first step is the synthesis of 5-methoxy-2-nitrophenol (1) which is available from commercial suppliers but it is quite expensive and only available in small amounts
The nmr data were completedwith I3cnmr values given for the cyclic hydroxamic acid 3
Summary
Benzoxazinoids are naturally occuring in a variety of plants like Secale cereale L. [I], Triticum aestivum L. or Zea mays L. [2] and especially in many important crop plants of the family Gramineae. Keywords Cyclic hydroxamic acid, DIMBOA, chemical data. The most important cyclic hydroxamic acids are 2,4-dihydroxy-2H-l,4benzoxazin-3(4H)-one (DIBOA) and 2,4-dihydroxy-7-methoxy-2H-I,4benzoxazin-3(4H)-one (DIMBOA) and so we synthesized the two molecules following known synthetic pathways [5, 61.
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