Abstract
A series of novel compounds, namely 1-(diethoxyphosphoryl)-3-(4-ones-1H-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-1H-1,2,3-triazol-1-yl)propan-2-yl 2-(naphthalen-1-yl)acetate (5-A3) and ethyl 1-(2-acetoxy-3-(diethoxyphosphoryl)propyl)-1H-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/hm2, 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/hm2) in the pot experiments.
Highlights
Imidazole glycerol phosphate dehydratase (IGPD) was recently discovered as a new potential target enzyme for the development of herbicides
IRL1695 was the first high-activity inhibitor of imidazole glycerol phosphate dehydratase (IGPD) (IC50 = 130 nM, pH = 7.5, Ki = 40 ± 6.5 nM, Km/Ki = 9.0 × 103). This compound was designed on the basis of the diazafulvene intermediate of IGPD [3,7]
Schweitzer suggested that the phenyl ring of â-carboxamido phosphates may contribute to a putative lipophilic interaction between the inhibitor and IGPD
Summary
Imidazole glycerol phosphate dehydratase (IGPD) was recently discovered as a new potential target enzyme for the development of herbicides. It catalyzes the conversion of imidazole glycerol phosphate (IGP) to imidazole acetol phosphate (IAP) in the histidine biosynthetic pathway [1]. Many high-activity inhibitors of IGPD such as (3-hydroxy-3-(1H-1,2,4-triazol-3-yl)propyl) phosphonic acid (IRL1695, Mori et al [3]) and (2-(3-phenoxypropanamido)-3-(1H-1,2,4-triazol-1-yl)propyl) phosphonic acid (Schweitzer et al [4]) were recently synthesized [5] While these inhibitors exhibited excellent enzymatic inhibitor activity, only the compound IRL1803 [3-hydroxy-3-(1H-[1,2,4]triazol-3yl)-cyclohexyl]-phosphonic acid (Mori et al [6]) elicited herbicidal activity, preventing weed growth at a concentration of 1 kg/hm. Many inhibitors of IGPD were reported, the mechanism of the IGP dehydratase reaction is still unknown
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