Atrazine Metabolism in Resistant Corn and Sorghum

Abstract

The metabolism of 2-chloro-4-ethylamino-6-isopropylamino-s-triazine (atrazine) in the resistant species, corn (Zea mays L.) and sorghum (Sorghum vulgare Pers.) was not the same. In corn, atrazine was metabolized via both the 2-hydroxylation and N-dealkylation pathways while sorghum metabolized atrazine via the N-dealkylation pathway. Atrazine metabolism in corn yielded the metabolites, 2-hydroxy-4-ethylamino-6-isopropylamino-s-triazine (hydroxyatrazine), 2-hydroxy-4-amino-6-isopropylamino-s-triazine (hydroxycompound I), and 2-hydroxy-4-amino-6-ethylamino-s-triazine (hydroxycompound II). None of these hydroxylated derivatives appeared as metabolites of atrazine in sorghum.Hydroxycompounds I and II were formed in 2 ways in corn: (1) by benzoxazinone-catalyzed hydrolysis of 2-chloro-4-amino-6-isopropylamino-s-triazine (compound I) and 2-chloro-4-amino-6-ethylamino-s-triazine (compound II) that were formed by N-dealkylation of atrazine and (2) by N-dealkylation of hydroxyatrazine, the major atrazine metabolite in corn. The interaction of the 2-hydroxylation and N-dealkylation pathways in corn results in the formation of the 3 hydroxylated non-phytotoxic derivatives of atrazine.