- Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action
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In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
- Lei, Kang,Li, Pan,Yang, Xue-Fang,Wang, Shi-Ben,Wang, Xue-Kun,Hua, Xue-Wen,Sun, Bin,Ji, Lu-Sha,Xu, Xiao-Hua
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p. 10489 - 10497
(2019/10/02)
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- The optically pure sodium alcoholate dextrorotary chlorine forefront of the method for the preparation of
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The invention relates to a preparation method of optically pure dextro cloprostenol sodium. The method comprises the following steps: using the combination of ketonic acid and S-phenylethylamine resolving agent, and carrying out chiral resolution to obtain S-propenylphosphonate with the structural formula of R-ketonic acid; then separating to obtain R-chlorone and preparing to obtain R-cloprostenol sodium. The preparation method has the benefits that the optically pure dextro cloprostenol sodium in the invention is called D-cloprostenol sodium for short, the using amount only needs one third of cloprostenol sodium being a racemic modification in current market, and the pesticide effect is obviously better than cloprostenol sodium with three times of using amount.
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Paragraph 0132 - 0134
(2018/02/04)
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- Synthesis of (±) travoprost and its analogs
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A new synthetic approach for the antiglaucoma agent, travoprost (1) has been developed in four steps from key intermediate (2). Key transformations include Horner-Wadsworth-Emmons reaction and separation of diastereomers to obtain (±) travoprost (1) and its analogs.
- Mudduluru, Harikrishna,Hindupur, Rama M.,Dubey, Pramod K.,Madhavaram, Shankar,Tatini, Lakshmikumar,Subbaraju, Gottumukkala V.
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experimental part
p. 234 - 241
(2012/04/18)
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- A new synthesis of 2-aryloxypropionic acids derivatives via selective mono-C-methylation of methyl aryloxyacetates and aryloxyacetonitriles with dimethyl carbonate
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A one-pot procedure for the mono-C-methylation of methyl aryloxyacetates and aryloxyaceto nitriles by dimethyl carbonate (DMC) is reported. The reaction is carried out in an autoclave at high temperatures (180-200°C) and in the presence of a base (K2
- Bomben, Andrea,Marques, Carlos A.,Selva, Maurizio,Tundo, Pietro
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p. 11573 - 11580
(2007/10/02)
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- PROSTANOIDS. XIX. THE SYNTHESIS OF 14C-LABELED CLOPROSTENOL
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A 1:3400 mixture of 2-14C-labelled methyl bromoacetate with the nonradioactive ester gave labelled dimethoxy-2-oxo-3-(m-chlorophenoxy)phosphonate which was used for the synthesis of 16-14C-labelled cloprostenol by the Corey strategy.
- Miftakhov, M. S.,Vostrikov, N. S.,Kuznetsov, O. M.,Kuvatov, Yu. G.,Murinov, Yu. I.,Tolstikov, G. A.
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p. 1072 - 1075
(2007/10/02)
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- Applicability of Hammett Equation to the Kinetics of Acid-catalysed Esterification of meta- and para-Substituted Phenoxyacetic Acids by Methanol
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Rate constants have been determined for the acid-catalysed esterification of meta- and para-substituted phenoxyacetic acids by methanol, with hydrogen chloride as catalyst.The applicability of the Hammett equation to the rate data has been examined.The para-substituted benzoic acids react slower than the corresponding para-substituted phenoxyacetic acids.The probable cause of this behaviour is discussed.
- Baliah, V.,Gurumurthy, R.
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p. 629 - 631
(2007/10/02)
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- Influence of meta- and para-Substituents on the Kinetics of Esterification of Phenoxyacetic Acids by Methanol
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The influence of meta- and para- substituents on the kinetics of acid-catalysed esterification of phenoxyacetic acids is discussed.In the case of para Cl, Br and I substituents, d-orbital resonance is suggested to explain the observed behaviour.The possibility of protonation of the methoxy oxygen in the acid medium employed is indicated to explain the slower rate of reaction of m- and p-methoxyphenoxyacetic acids.
- Baliah, V.,Gurumurthy, R.
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p. 1082 - 1083
(2007/10/02)
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