Agricultural Research Service, United States Department of Agriculture, Fargo, North Dakota 58102.
Plant Physiol. 1968 Dec;43(12):1925-30. doi: 10.1104/pp.43.12.1925.
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.
2-氯-4-乙氨基-6-异丙氨基-均三嗪（阿特拉津）在抗性物种玉米（Zea mays L.）和高粱（Sorghum vulgare Pers.）中的代谢途径不同。在玉米中，阿特拉津通过 2-羟化和 N-脱烷基化途径代谢，而高粱通过 N-脱烷基化途径代谢阿特拉津。玉米中阿特拉津的代谢产物为 2-羟基-4-乙氨基-6-异丙氨基-均三嗪（羟基阿特拉津）、2-羟基-4-氨基-6-异丙氨基-均三嗪（羟基化合物 I）和 2-羟基-4-氨基-6-乙氨基-均三嗪（羟基化合物 II）。高粱中没有这些羟基化衍生物作为阿特拉津的代谢产物出现。羟基化合物 I 和 II 在玉米中有两种形成方式：（1）通过苯并恶嗪酮催化水解 2-氯-4-氨基-6-异丙氨基-均三嗪（化合物 I）和 2-氯-4-氨基-6-乙氨基-均三嗪（化合物 II），这些化合物是通过阿特拉津的 N-脱烷基化形成的，（2）通过玉米中阿特拉津的主要代谢产物羟基阿特拉津的 N-脱烷基化形成。玉米中 2-羟化和 N-脱烷基化途径的相互作用导致阿特拉津的 3 种羟基非毒性衍生化合物的形成。
