The photostimulated reaction of methyl 2,5‐dichloro benzoate (1) or methyl 3,6‐dichloro‐2‐methoxy benzoate (7) with −SnMe3 ions give good yields of the disubstitution products by the SRN1 mechanism in liquid ammonia. Conversely, in dark conditions, substrate 1 reacts with −SnMe3 ions to afford the mono‐substitution products by the SRN1 mechanism. On the other hand, substrate 7 reacts with −SnMe3 ions in dark conditions to give mono‐reduced product probably by a halogen metal exchange reaction. In addition, the photostimulated reaction of 2‐chloro‐N 4‐ethyl‐N 6‐isopropyl‐1,3,5‐triazin‐4,6‐diamine (Atrazine, 11) with −SnMe3 ions affords the reduced and substitution products in liquid ammonia‐DMSO as co‐solvent. Copyright © 2006 John Wiley & Sons, Ltd.

We report the synthesis and phytotoxicity of the compounds involved in the S RN 1-Stille reactions such as methyl 2,5-diphenylbenzoate (6), methyl 5-chloro-2-phenylbenzoate (7) and methyl 2-methoxy-3,6-diphenylbenzoate (8) as well as the phytotoxicity of intermediates. 8 has a good herbicide activity compared to Disugran and it isn't a chlorinated compound.

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