Synthesis and Herbicidal Activity of α-(Substituted Phenoxybutyryloxy or Valeryloxy)alkylphosphonates and 2-(Substituted Phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

Abstract

On the basis of our work on the modification of alkylphosphonates 1, a series of α-(substituted phenoxybutyryloxy or valeryloxy)alkylphosphonates (4-5) and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one (6) were designed and synthesized. The bioassay results indicated that 14 of title compounds 4 exhibited significant postemergence herbicidal activity against velvetleaf, common amaranth, and false daisy at 150 g ai/ha. Compounds 5 were inactive against all tested weeds. Compounds 6 exhibited moderate to good inhibitory effect against the tested dicotyledonous weeds. Structure-activity relationship (SAR) analyses showed that the length of the carbon chain as linking bridge had a great effect on the herbicidal activity. Broad-spectrum tests of compounds 4-1, 4-2, 4-9, 4-30, and 4-36 were carried out at 75 g ai/ha. Especially, 4-1 exhibited 100% inhibition activity against the tested dicotyledonous weeds, which was higher than that of glyphosate.

Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible‐Light–Nickel Catalysis

“…Finally, the synthetic application of this nickel‐based photocatalytic transformation was demonstrated by the concise synthesis of MCPB ( 7 ), which exhibits potent biological activity [Scheme , Eq. (1)] . Moreover, estrone could be derivatized to give the desired carboxylic acid 8 directly in moderate yield without separation by column chromatography [Scheme , Eq.…”

“…(1)]. [16] Moreover,e strone could be derivatized to give the desired carboxylic acid 8 directly in moderate yield without separation by column chromatography [Scheme 2, Eq. (2)].…”

Organocatalytic, Chemoselective Hydrophosphenylation/oxa-Michael Addition Cascade toward Diastereo- and Enantioenriched 1,3-Dihydroisobenzofuryl Phosphonates

“…FT-IR (neat): 3426, 2106, 2334, 1658, 1421, 1262, 840 cm −1 . 1 H NMR (500 MHz, CDCl 3 ) δ 8.07 −8.02 (m, 2H), 7.48−7.43 (m, 1H), 7.37−7.33 (m, 2H), 7.30 (dt, J = 4.2, 3.3 Hz, 1H), 6.99−6.91 (m, 2H), 6.12− 6.04 (m, 1H), 5.53 (s, 1H), 3.88 (s, 3H), 3.86 (dd, J = 6.2 Hz, 1H), 3.84 (d, J = 7.8 Hz, 3H), 3.67 (d,J = 10.3 Hz,3H), 3.28 (dd, J = 16.6, 5.1 Hz, 1H). 13 Dimethyl The enantiomeric ratio was determined by HPLC analysis using a Daicel Chiralpak OZ-3 column (hexane/2-propanol = 50:50, flow rate = 1.0 mL/min, λ = 254 nm), t R = 9.3 min (minor), and t R = 27.8 min (major).…”

“…FT-IR (neat): 3415, 2111,1645, 1461, 1326,1124, 1031, 418 cm −1 . 1 H NMR (500 MHz, CDCl 3 ) δ 7.47−7.42 (m, 1H), 7.37 (t, J = 3.7 Hz, 1H), 7.35 (d, J = 5.3 Hz, 3H), 7.30 (d, J = 4.1 Hz, 1H), 6.08 (td, J = 8.9, 4.7 Hz, 1H), 5.52 (s, 1H), 3.93 (s, 6H), 3.93 (d, J = 1.0 Hz, 3H), 3.91 (s, 3H), 3.86−3.81 (m, 1H), 3.65 (d,J = 10.4 Hz,3H),3.22 (dd,J = 16.4,4.6 Hz,1H). 13 Dimethyl ((1S,3R)-3-(2-([1,1′-Biphenyl]-4-yl)-2-oxoethyl)-1,3-dihydroisobenzofuran-1-yl)phosphonate (3h).…”

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.45 (dd, J = 4.3, 2.3 Hz, 1H), 7.36−7.31 (m, 2H), 7.25−7.19 (m, 1H), 5.87 (dd, J = 13.9, 8.9 Hz, 1H), 5.51 (s, 1H), 3.86 (d,J = 10.6 Hz,3H),3.71 (d,J = 10.3 Hz,3H),3.20 (dd,J = 16.5,8.0 Hz,1H),2.86 (dd,J = 16.5,5.0 Hz,1H),2H), 1.69−1.58 (m, 2H), 1.39−1.25 (m, 4H), 0.91 (t, J = 7.1 Hz, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 209.0, 141.5 (d,J = 7.3 Hz),134.7 (d,J = 2.8 Hz), 128.4 (dd, J = 57.0, 2.9 Hz), 122.5 (d, J = 3.0 Hz), 121.6 (d, J = 2.7 Hz), 81.8 (d, J = 1. 5 Hz),79.6,78.2,54.0 (d,J = 7.2 Hz), 53.1 (d, J = 6.5 Hz), 49.9 (d,J = 3.6 Hz),43.9,31.4,23.2,22.4,13.9.…”