Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine

Wang, Wei; He, Hongwu; Zuo, Na; Zhang, Xin; Lin, Ji-Sheng; Chen, Wei; Peng, Hao

doi:10.1016/j.jfluchem.2012.06.020

Cited by 12 publications

(7 citation statements)

References 12 publications

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“…Following the procedure described for 8a – f , compounds 18a , b were obtained with yields of 60–90%. Compounds 18a , b have been reported in the literature …”

Section: Methodsmentioning

confidence: 99%

“…Furthermore, compounds 3 have been designed and synthesized by the introduction of a cyclophosphonate moiety into the phosphonate part of structure 1 . Compounds 3-2 and 3-3 showed high activity with an inhibition effect of 70–100% at 75 g ai/ha against all of the tested broadleaf weeds and against tested dicotyledons, such as velvetleaf, leaf mustard, and false daisy, which indicated that they could be developed as selective postemergence herbicides …”

Section: Introductionmentioning

confidence: 97%

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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

Wei

Zhang

Zhou

et al. 2016

J. Agric. Food Chem.

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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.

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“…Following the procedure described for 8a – f , compounds 18a , b were obtained with yields of 60–90%. Compounds 18a , b have been reported in the literature …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

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

Wei

Zhang

Zhou

et al. 2016

J. Agric. Food Chem.

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“…A number of articles reported the acylation of α-hydroxyphosphonates 1 with carboxylic acid chlorides in the presence of triethylamine [ 73 , 74 , 75 ] or pyridine [ 76 , 77 ] as the hydrochloric acid scavenger. Among the –C(O)Cl reagents, phenoxyacetyl chloride derivatives 18 are frequently applied acylating agents [ 70 , 71 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 ].…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

“…In general, the reaction of α-hydroxyphosphonates 1 with phenoxyacetyl chlorides 18 required a reaction time of 3–7 h, and the corresponding α-acyloxyphosphonates 19 were isolated in yields of 53–89% ( Scheme 8 ) [ 78 ]. The compounds 19 thus-obtained are popular target molecules, as a series of related derivatives exhibited herbicidal activity [ 70 , 76 , 77 , 78 , 79 , 80 , 83 , 84 ].…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

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“…Fluorine substitution has been extensively investigated in drug designing and development as a means of enhancing pharmacological activity and increasing metabolic or chemical stability. Fluorine containing compounds possess fungicidal 16 , herbicidal 17 , antiviral 18 , cytotoxic 19 , antipyretic 20 , insecticidal 21 and analgesic 22 activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Screening of Novel (E)-3-(3-(2-(4-Fluorophenyl)-4-Methylthiazol-5-Yl)-1-Phenyl-1h-Pyrazol-4-Yl)-1-(2-Hydroxyphenyl)prop-2-en-1-Ones

Akolkar¹,

Karale²,

Darekar³

2019

Int Res J Pharm

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A novel series of chalcone 3a-e was prepared by conventional Claisen-Schmidt condensation of 3-(2-(4-fluorophenyl)-4-methylthiazol-5-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 1 with substituted 2-hydroxyacetophenones using 40 % aq. KOH in ethanol. The starting material 3-(2-(4-fluorophenyl)-4-methylthiazol-5-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 1 was synthesized by reacting 1-[2-(4-fluorophenyl)-4-methyl-1,3-thiazol-5-yl]ethan-1one with phenyl hydrazine followed by reaction with DMF/ POCl3. The structures of all newly synthesized compounds were assigned on the basis of spectral data such as IR, 1 H-NMR and mass. These compounds3a-e were evaluated for their antibacterial activity against gram-negative Pseudomonas fluorescens and Escherichia coli and gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus. Compounds 3a-e showed good activity against gram positive bacterial strain of Bacillus subtilis compared to the standard drug Ampicillin at a concentration of 100 μg/mL also compounds 3a, 3c, 3d and 3e showed good activity at a concentration of 30 μg/mL but none of them was as active as standard Ampicillin.

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Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine

Cited by 12 publications

References 12 publications

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

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

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Antibacterial Screening of Novel (E)-3-(3-(2-(4-Fluorophenyl)-4-Methylthiazol-5-Yl)-1-Phenyl-1h-Pyrazol-4-Yl)-1-(2-Hydroxyphenyl)prop-2-en-1-Ones

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