Sugarcane atrazine metabolism

Simazine and atrazine have little effect on com, sorghum, sugarcane, and some other grasses, apparently because of the ability of the plant to metabolize the parent molecule. Com and wheat gave a cyclic hydrox-amate, namely, the 2-D-glucoside of 2,4-dihydroxy-7-methoxy-l, 4-benzox-azin-3-one (11), m.p. 168-70°, aglycon m.p. 156-7 (dec.), believed to... 

The metabolism of atrazine and a series of 2-chloro-.v-lriaz.ines were reported by Lamoureux et al. (1972) in excised leaf or shoot tissue of barley, corn, sorghum, and sugarcane. The authors found that the primary route of metabolism was the displacement of the 2-chloro group with glutathione or 7-glutamylcysteine. The overall rate of metabolism in susceptible barley was much slower than in tolerant crops. 

Figure 7.2 Metabolism of atrazine in sugarcane plants by (a) ALdcal kylation of the side chains, (b) hydrolysis of the 2-chloro group followed by JV-dealkylation, and (c) displacement of the 2-chloro by glutathione conjugation (Larson and Ash, 1993).

Figure 7.4 Metabolism of the 5-cysteine conjugate of atrazine in sugarcane plants (Larson and Ash, 1993).

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