A series of novel compounds, namely 1-(diethoxyphosphoryl)-3-(4-ones-1
H-1,2,3-triazol-1-yl)propan-2-yl carboxylic esters, were designed on the basis of the diazafulvene intermediate of imidazole glycerol phosphate dehydratase (IGPD) and high-activity inhibitors of IGPD, and synthesized as inhibitors targeting IGPD in plants. Their structures were confirmed
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A series of novel compounds, namely 1-(diethoxyphosphoryl)-3-(4-ones-1
H-1,2,3-triazol-1-yl)propan-2-yl carboxylic esters, were designed on the basis of the diazafulvene intermediate of imidazole glycerol phosphate dehydratase (IGPD) and high-activity inhibitors of IGPD, and synthesized as inhibitors targeting IGPD in plants. Their structures were confirmed by
1H-NMR,
13C-NMR,
31P-NMR and HR-MS. The herbicidal evaluation performed by a Petri dish culture method showed that most compounds possessed moderate to good herbicidal activities. Six compounds were chosen for further herbicidal evaluation on barnyard grass by pot experiments. 1-(Diethoxyphosphoryl)-3-(4-phenyl-1
H-1,2,3-triazol-1-yl)propan-2-yl 2-(naphthalen-1-yl)acetate (
5-A3) and ethyl 1-(2-acetoxy-3-(diethoxyphosphoryl)propyl)-1
H-1,2,3-triazole-4-carboxylate (
5-B4) showed good herbicidal activities. Compared with the compounds with the best herbicidal activity ever reported, both compounds
5-A3 and
5-B4, which can inhibit the growth of barnyard grass at the concentration of 250g/hm
2, efficiently gave rise to a nearly 4-fold increase of the herbicidal potency. However, their herbicidal activities were lower than that of acetochlor (62.5 g/hm
2) in the pot experiments.
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