- Direct electrochemical oxidation of a pesticide, 2,4-dichlorophenoxyacetic acid, at the surface of a graphite felt electrode: Biodegradability improvement
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Pesticides' biorecalcitrance can be related to the presence of a complex aromatic chains or of specific bonds, such as halogenated bonds, which are the most widespread. In order to treat this pollution at its source, namely in the case of highly concentrated solutions, selective processes, such as electrochemical processes, can appear especially relevant to avoid the possible generation of toxic degradation products and to improve biodegrad- ability in view of a subsequent biological mineralization. 2,4-D was found to be electroactive in oxidation, but not in reduction, and the absence of hydroxyl radicals formation during the electrochemical step was demonstrated, showing that the pretreatment can be considered as a direct electrochemical process instead of an advanced electrochemical oxidation process. The presence of several degradation products in the oxidized effluent showed that the pretreatment was not as selective as expected. However, the relevance of the proposed combined process was confirmed since the overall mineralization yield was close to 93%.
- Fontmorin, Jean-Marie,Fourcade, Florence,Geneste, Florence,Soutrel, Isabelle,Floner, Didier,Amrane, Abdeltif
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Read Online
- Design, synthesis, anticancer evaluation and molecular docking study of novel 2,4-dichlorophenoxymethyl-based derivatives linked to nitrogenous heterocyclic ring systems as potential CDK-2 inhibitors
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A novel series of 2,4-dichlorophenoxymethyl-based derivatives 4-18 bearing various nitrogenous heterocyclic systems have been designed and synthesized through molecular hybridization approach. The anti-proliferative activity of all newly synthesized derivatives was established against human HCT-116 and MCF-7 cancer cell lines. The structure–activity relationship (SAR) studies exhibited that the derivatives incorporated with pyrido[3,2-d]pyrimidine, naphtho[2,3-e][1,3]oxazine-5-sulfonic acid, benzo[d]thiazole and benzo[d]oxazole scaffolds revealed the highest cytotoxic activities comparing with doxorubicin as a reference drug. The promising derivatives 5, 9, 13 and 15 were subjected to enzymatic inhibitory assessment against CDK-2/cyclin A2 using roscovitine as a standard. Concerning their effects upon the apoptotic process, they upregulated Bax, p-53 and caspase-3 levels and downregulated Bcl-2, causing induction of apoptosis. Moreover, the in silico molecular docking was applied to investigate the possible binding modes and orientations within the active site of CDK-2.
- Almehizia, Abdulrahman A.,Amr, Abd El-Galil E.,El-Sayed, Amira A.,Nossier, Eman S.
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- The invention relates to an acyl fluoride compound reduction and deuteration synthesis α, α - dideuterium alcohol. Method for deuterated drugs
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The invention relates to an α, α - dideuterium-substituted alcohol compound and a reduction deuteration method for preparing an acyl fluoride compound of α, α - dideuterium-substituted alcohol compounds, characterized in that α, α - dideuterium-substituted alcohol compounds represented by the general formula 2 (1) are reacted in an organic solvent I by a deuterium donor reagent. The method solves the problems that in the prior art α, α - dideuterium-substituted alcohol compounds are prepared by using inflammable reductant, poor selectivity and atomic economy, the invention establishes a method for reducing and deuteration of acyl fluoride compounds based on single electron transfer reduction deuteration reaction. The method can be used for preparing α, α - dideuterium-substituted alcohol compounds, and has the advantages of high product deuterium substitution rate, good regioselectivity, good chemical selectivity, low reagent price, simple operation, mild conditions and wide substrate application range.
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Paragraph 0131-0137
(2021/08/25)
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- 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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- Esterquat herbicidal ionic liquids (HILs) with two different herbicides: Evaluation of activity and phytotoxicity
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Herbicidal ionic liquids (HILs) constitute a new concept in crop protection products. Their main advantage is the potential to combine the efficiency of traditional herbicides with low vapour pressure and adjustable water solubility which leads to improved environmental safety in the agricultural sector. Among many strategies to obtain new HILs, esterquats seem to be well suited for modification since both the cation and anion may be constituents of herbicides. In the framework of this study 16 new esterquat HILs were synthetized based on standard herbicides: 2,4-D, MCPA, MCPP, 4-CPA, Clopyralid and Dicamba. Germination tests performed on agricultural soil using cornflower indicated the best two HILs. Furthermore, analysis of the toxicological effects of HILs on wheat plants revealed an additional advantage of the two selected HILs. The glutathione (GSH) content and glutathione S-transferase (GST) activity showed a lower oxidative stress level in wheat plants treated with examined HILs, respectively, in comparison to a mixture of reference compounds. Finally the Ames test was applied in order to analyse the mutagenic activity of the two selected HILs.
- Syguda, Anna,Gielnik, Anna,Borkowski, Andrzej,Wo?niak-Karczewska, Marta,Parus, Anna,Piechalak, Aneta,Olejnik, Anna,Marecik, Roman,?awniczak, ?ukasz,Chrzanowski, ?ukasz
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supporting information
p. 9819 - 9827
(2018/06/18)
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- Synthesis and insecticidal activity of rotenone analogues
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Rotenone, one of traditional botanical insecticide, has been used more than one hundred years. A variety of rotenone derivatives were designed and synthesized in recent years due to environmental benign character and not easy to generate insecticide resistance. This paper described the molecular design, synthesis, and insecticidal activities of a series of rotenone analogues and 2-substituted rotenone derivatives. The preliminary bioassay showed that isorotenone and 2-rotenone nicotinate is equal to rotenone's against Musca domestica.
- Zhicheng, Liu,Dingxin, Jiang,Hanhong, Xu,Xiaohua, Zheng
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p. 1063 - 1070
(2018/10/26)
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- Multi-substituted phenylpyrazole derivatives and preparation method and application thereof
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The invention discloses multi-substituted phenylpyrazole derivatives and a preparation method and an application thereof in preparation of insecticides, wherein the multi-substituted phenylpyrazole derivatives have the structure described in the specification. The multi-substituted phenylpyrazole derivatives have the insecticidal efficacy better than or equivalent to that of conventional commoditized pesticides on the market. The compounds can be used for prevention and control of pests in agriculture, forestry or hygiene, especially for prevention and control of insecticide-resistant insects.The preparation method has the advantages of high yield, fewer steps and simple operation.
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Paragraph 0053; 0054; 0055; 0056; 0057; 0058; 0061-0065
(2018/03/28)
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- Synthesis and Biological Activity of 4-[(Substituted Phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one
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A series of novel 4-[(substituted phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o were synthesized. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 4b, 4c, 4f, 4h, 4i, and 4j possess 90–100% inhibition against the growth of roots of both rape and barnyard grass at 10 mg/L. Moreover, the title compounds 4f, 4g, and 4h possess 75–89% inhibition against Botrytis cinerea at the concentration of 50 mg/L.
- Sheng, Xijun,Zhou, Yuan,Zhang, Shasha,Peng, Hao,He, Hongwu
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p. 165 - 170
(2017/02/03)
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- Synthesis and Antimicrobial Activity of Novel 2-Substituted Phenoxy-N-(4-substituted Phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-yl)acetamide Derivatives
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A series of 2-substituted phenoxy-N-(4-substituted phenyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2-yl)acetamide derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r, 8s, 8t was synthesized by the reaction of phenoxyacetyl chloride 7 with intermediate 4-substituted phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine 5. Their structures were confirmed by 1H NMR, 13C NMR, MS, IR, and elemental analyses. The synthesized compounds were also screened for their antimicrobial activity against three types of plant fungi (Gibberella zeae, Phytophthora infestans, and Paralepetopsis sasakii) and two kinds of bacteria [Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac)] showing promising results. In particular, 8b, 8f, 8g, and 8h exhibited excellent antibacterial activity against Xoo, with 50% effective concentration (EC50) values of 35.2, 80.1, 62.5, and 82.1 μg/mL, respectively, which are superior to the commercial antibacterial agent bismerthiazol (89.9 μg/mL). The preliminary structure–activity relationship studies of these compounds are also briefly described.
- Liao, Guo-Ping,Zhou, Xia,Xiao, Wei,Xie, Yan,Jin, Lin-Hong
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p. 1506 - 1513
(2017/03/27)
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- 7 - aryloxyacetic acetyloxy coumarin compound and its application in pesticide (by machine translation)
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The invention provides a 7 - aryloxyacetic acetyloxy coumarin compound and its application in pesticide, preparation are as follows: 1, will contain different substituents of the resorcinol add to the reaction bottle of the concentrated sulfuric acid, stirring and dissolving, ice water bath cooling slowly dripping acetoacetate compound, then completing, ice water bath cooling under reaction 1h; reacting at room temperature 24h; violent stirring into ice water in the mixture, a yellow precipitation, filtered, the filter cake is anhydrous ethanol recrystallize to get 7 - hydroxy coumarin compound; 2, 2, 4 - dichloro acid with oxalyl dissolved in CH2 Cl2 In the solvent, dropping N, N - dimethyl formamide, room temperature reaction 2h make acyl chloride; 3, containing 7 - hydroxy coumarin compounds and acyl chloride in the organic solvent, under a certain temperature, adding catalyst, reaction after a period of time, re-crystallization to obtain the 7 - aryloxyacetic acetyloxy coumarin compound. The compounds of the invention have very high herbicidal activity. (by machine translation)
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Paragraph 0040; 0041; 0042
(2017/07/23)
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- Coumarin-aryloxy carboxylic ester compound and application thereof in pesticide
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The invention provides a coumarin-aryloxy carboxylic ester compound and application thereof in pesticides. A preparation method comprises the following steps of 1, adding resorcinol containing different substituent groups into a reaction bottle containing concentrated sulfuric acid, stirring and dissolving, slowly dripping an acetacetic ester compound while being cooled by an ice-water bath, and reacting for 1h while cooling by the ice-water bath; reacting for 24h at room temperature; pouring into an ice and water mixture under intensely stirring, generating a yellow precipitate, sucking and filtering, and recrystallizing a filter cake by absolute ethyl alcohol, so as to obtain a 7-hydroxycoumarin compound; 2, dissolving 2,4-dichlorphenoxyacetic acid and oxalyl chloride into a CH2Cl2 (methylene chloride) solvent, dripping N,N-dimethylformamide, and reacting for 2h at room temperature, so as to obtain acyl chloride; 3, adding a catalyst into an organic solvent containing the 7-hydroxycoumarin compound and the acyl chloride at certain temperature, reacting for a period of time, and recrystallizing, so as to obtain the coumarin-aryloxy carboxylic ester compound. The coumarin-aryloxy carboxylic ester compound has higher weeding activity.
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Paragraph 0049; 0050; .0051
(2017/07/20)
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- Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate
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(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.
- Mo, Wenyan,Shi, Yanxia,He, Junbo,Li, Baoju,Peng, Hao,He, Hongwu
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p. 183 - 187
(2016/02/10)
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- Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives
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A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by1H NMR,13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000?mg/L. Compound 6q presented the best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50?mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.
- Huo, Jing-Qian,Ma, Liu-Yong,Zhang, Zhe,Fan, Zhi-Jin,Zhang, Jin-Lin,Beryozkina, Tetyana V,Bakulev, Vasiliy A
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p. 1547 - 1550
(2016/09/23)
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- Substituted phenoxyacetate compound as well as preparation method and applications thereof
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The invention provides a substituted phenoxyacetate compound as well as a preparation method and applications thereof. The substituted phenoxyacetate compound disclosed by the invention is prepared by taking substituted phenoxyacetate (2,4-D, agroxone) as a raw material through the steps of acylation and nucleophilic substitution, and the structural formula of the substituted phenoxyacetate compound is shown in a formula I. The prepared compound is novel in structure, and has the advantages of high activity, quick acting, strong selectivity, and the like. The compound is simple in preparation process, environmentally friendly, and short in reaction process. The compound has good biological activity to broadleaf weeds (e.g., kochia scoparia, quinoa), and the biological activity of part of the compound is obviously higher than that of the parent compound.
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Paragraph 0039-0040
(2016/10/09)
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- A one-pot synthesis of tetrazolones from acid chlorides: Understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs
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A one-pot and scalable synthesis of tetrazolones (tetrazol-5-ones) from acid chlorides using azidotrimethylsilane is presented. The reaction tolerates many functional groups and can furnish aryl-, heteroaryl-, alkenyl-, or alkyl-substituted tetrazolone products in moderate to excellent yield (14-94%). No reduction in yield was observed when the reaction was undertaken on a larger-scale (20-36 g). The method could be used for the late-stage functionalization of pharmaceuticals, to provide tetrazolone congeners of the marketed drugs aspirin, indomethacin, probenecid, telmisartan, bexarotene, niacin (vitamin B3), and the active metabolite of the recently-launched immuno-modulatory agent, BG-12 (Tecfidera). The ability of a tetrazolone group to serve as a bioisostere of a carboxylic acid, and to improve drug pharmacokinetic profiles is also highlighted.
- Duncton, Matthew A. J.,Singh, Rajinder
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supporting information
p. 9338 - 9342
(2016/10/13)
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- 6-aryloxyacetic acetoxy orange ketones compound and the application of the pesticides
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The invention relates to a 6-aryloxy acetoxy aurone compound and an application thereof on a pesticide, and belongs to the technical field of herbicides. The general formula of the 6-aryloxy acetoxy aurone compound is as shown in the specification, wherein R1 is hydrogen, halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 alkylamino, and R2 is the hydrogen and the C1-C4 alkyl. The invention provides a lot of novel chemical structures and novel compounds. A biological activity measurement result indicates that the compound I has very high weeding activity.
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Paragraph 0055; 0056
(2016/12/01)
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- Substituted phenoxyacetic acid weeding oligomer as well as preparation method and application thereof
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The invention provides a substituted phenoxyacetic acid weeding oligomer as well as a preparation method and an application thereof. Substituted phenoxyacetic acid (2,4-D, agroxone) and a nucleophilic bridging body are taken as raw materials, and acylation, nucleophilic substitution reaction are carried out, so that the substituted phenoxyacetic acid weeding oligomer is obtained, and a structural formula of the substituted phenoxyacetic acid weeding oligomer is shown in a formula I. The prepared compound has good biological activity on broadleaf weeds (such as kochia scoparia and chenopodium album), and biological activity of some compounds is obviously higher than that of a parent compound. The substituted phenoxyacetic acid weeding oligomer has the advantages of simple preparation technology, environmental friendliness and short reaction mechanism.
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Paragraph 0064; 0065
(2016/12/01)
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- Tetrazolones as a Carboxylic Acid Bioisosteres
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The present disclosure provides compounds that include a tetrazolone derivative of a carboxyl group of an active agent. This disclosure also relates to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, and processes for preparing these compounds.
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Paragraph 0310; 0311; 0312; 0313; 0314; 0315
(2016/08/17)
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- Synthesis and Herbicidal Activities of Sodium Methyl(α-(Substituted Phenoxyacetoxy)Alkyl)Phosphinates
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A series of sodium methyl(α-(substituted phenoxyacetoxy)alkyl)phosphinates was designed and synthesized. Their structures were confirmed by IR, 1H NMR and elemental analysis, and some of them were further confirmed by MS. The results of bioassay showed that most of title compounds exhibited moderate to good herbicidal activities against the root of barnyard grass and rape at 10~100 mg/L.
- Wang, Tao,Gao, Yujiao,Peng, Hao,He, Hongwu
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p. 972 - 977
(2015/08/04)
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- Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates
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A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.
- Wang, Tao,Wang, Wei,Peng, Hao,He, Hongwu
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p. 173 - 179
(2015/01/30)
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- Synthesis and Biological Activity of O-Methyl Methyl 1-(Substituted Phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates
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A series of novel O-methyl methyl 1-(substituted phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 5c, 5d, and 5g possess 90-100% inhibition against the tested plants at the concentration of 10 mg/L and 100 mg/L, whereas the title compounds 5a, 5b, 5c, and 5h possess 70-94% inhibition against Phyricularia grisea and Sclerotinia sclerotiorum at the concentration of 50 mg/L.
- Wang, Tao,Peng, Hao,He, Hongwu
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p. 1260 - 1263
(2015/08/06)
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- Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality
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Several new 2-(2-phenoxyacetamido)benzamides 17a-v, 21 and 22 were synthesized by stirring in pyridine the acid chlorides 16a-e and the appropriate5-R-4-R1-2-aminobenzamide 15a-e and initially evaluated in vitro for antiproliferative activity against the K562 (human chronic myelogenous leukemia) cell line. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). The most active compounds caused an arrest of K562 cells in the G0-G1 phase of cell cycle and induction of apoptosis, which was mediated by caspase activation.
- Raffa, Demetrio,Maggio, Benedetta,Plescia, Fabiana,Cascioferro, Stella,Raimondi, Maria Valeria,Cancemi, Gabriella,D'Anneo, Antonella,Lauricella, Marianna,Cusimano, Maria Grazia,Bai, Ruoli,Hamel, Ernest,Daidone, Giuseppe
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p. 6305 - 6316
(2015/10/05)
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- An anti-biodegradable hydrophobic sulfonate-based acrylamide copolymer containing 2,4-dichlorophenoxy for enhanced oil recovery
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We report here a novel anti-biodegradable hydrophobic acrylamide copolymer that was prepared from acrylamide, acrylic acid, sodium 3-(allyloxy)-2-hydroxypropane-1-sulfonate and N-allyl-2-(2,4-dichlorophenoxy) acetamide using the 2,2'-azobis(2-methylpropionamide) dihydrochloride initiation system. Subsequently, the copolymer was characterized by FT-IR, 1H NMR, TG-DTG and water-solubility. And the biodegradability test indicated that the copolymer was not deemed to be readily biodegradable via a closed bottle test established by the Organization for Economic Co-operation and Development (OECD 301 D). Meanwhile the copolymer could significantly enhance the viscosity of the aqueous solution in comparison with partially hydrolyzed polyacrylamide. A viscosity retention of 51.9% indicated the result of a dramatic improvement of temperature tolerance. And then the excellent salt resistance, shear resistance, viscoelasticity, long-term stability of the copolymer could be obtained, which provides a good theoretical foundation for the application in enhanced oil recovery. In addition, this copolymer exerted stronger mobility control ability with a resistance factor of 22.1 and a residual resistance factor of 5.0, and superior ability for enhanced oil recovery of 12.9%. Hence, the copolymer has potential application for enhanced oil recovery in high-temperature and high-salinity reservoirs.
- Gou, Shaohua,He, Yang,Zhou, Lihua,Zhao, Peng,Zhang, Qin,Li, Shiwei,Guo, Qipeng
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supporting information
p. 9265 - 9274
(2015/12/01)
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- Discovery of a novel series of phenyl pyrazole inner salts based on fipronil as potential dual-target insecticides
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A series of novel phenyl pyrazole inner salt derivatives based on fipronil were designed and synthesized in the search for dual-target insecticides. These compounds were designed to target two families of nicotinic acetylcholine receptors and γ-aminobutyric acid receptors. The insecticidal activities of the new compounds against diamondback moth (Plutella xylostella) were evaluated. The results of bioassays indicated that most of the inner salts showed moderate to high activities, of which the phenyl pyrazole inner salts containing quinoline had excellent biological activity. Previous structure-activity relationship studies revealed that a suitable structure of the quaternary ammonium salts was critical for the bioactivity of phenyl pyrazole inner salts, which contribute to exposing the cationic nitrogen to bind to the receptor (for instance, nicotinic acetylcholine receptors) and possibly interact with the receptor via hydrogen bonding and cooperative π-π interaction. The present work demonstrates that the insecticidal potency of phenyl pyrazole inner salts holds promise for the development new dual-target phenyl pyrazole insecticides.
- Jiang, Dingxin,Zheng, Xiaohua,Shao, Guang,Ling, Zhang,Xu, Hanhong
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p. 3577 - 3583
(2014/05/20)
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- Discovery of a novel series of phenyl pyrazole inner salts based on fipronil as potential dual-target insecticides
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A series of novel phenyl pyrazole inner salt derivatives based on fipronil were designed and synthesized in the search for dual-target insecticides. These compounds were designed to target two families of nicotinic acetylcholine receptors and γ-aminobutyric acid receptors. The insecticidal activities of the new compounds against diamondback moth (Plutella xylostella) were evaluated. The results of bioassays indicated that most of the inner salts showed moderate to high activities, of which the phenyl pyrazole inner salts containing quinoline had excellent biological activity. Previous structure-activity relationship studies revealed that a suitable structure of the quaternary ammonium salts was critical for the bioactivity of phenyl pyrazole inner salts, which contribute to exposing the cationic nitrogen to bind to the receptor (for instance, nicotinic acetylcholine receptors) and possibly interact with the receptor via hydrogen bonding and cooperative π-π interaction. The present work demonstrates that the insecticidal potency of phenyl pyrazole inner salts holds promise for the development new dual-target phenyl pyrazole insecticides.
- Jiang, Dingxin,Zheng, Xiaohua,Shao, Guang,Ling, Zhang,Xu, Hanhong
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p. 3577 - 3583
(2015/04/22)
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- Synthesis, Structure, and Properties of the 2-[5-(Aryloxyacetyl)-Amino-1,3,4-Thiadiazol-2-Ylthio] Propionate Derivatives
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A series of novel 2-[5-(aryloxyacetyl)-amino-1,3,4-thiadiazol-2-ylthio] propionate derivatives were synthesized in high yield, and their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis, coupled with one selected single-crystal X-ray structure determination. The herbicidal activities of target compounds were assessed. The preliminary bioassay results showed that some compounds exhibited moderate to strong herbicidal symptoms in preemergence and postemergence tests. At 150 g/ha, S. tritici. show tolerance, while E. crus-galli L., E. Dahuricus, A. retroflexus, and C. glaucum L. were killed or severely injured. The activity of some compounds was comparable to the commercial herbicide 2,4-D. A suitable electron-withdrawing substituent at the 2-and/or 4-position of the phenyl ring was essential for high herbicidal activity. Moreover, the antifungal activities of the compounds have also been studied. The compounds were found to possess broad-spectrum antifungal activity.
- Hu, Bing,Zhai, Yue-Yuan,Zhang, Ling,Zhang, You-Ming,Wei, Tai-Bao
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p. 1337 - 1345
(2015/10/29)
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- LABILE ESTERS OF AGROCHEMICALS FOR CONTROLLED RELEASE AND REDUCTION OF OFF-SITE MOVEMENT
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The present invention relates to esters of carboxylic acid agrochemicals comprising a labile protecting group and having formula (I). Certain of the esters of carboxylic acid agrochemicals do not undergo hydrolysis to a significant degree in the dark, but are cleaved to regenerate the parent carboxylic acid agrochemical when exposed to light. Others of the esters of carboxylic acid agrochemicals undergo hydrolysis under both light and dark conditions. The present invention further relates to methods for the controlled release of a carboxylic acid agrochemicals, and to methods of controlling unwanted plants comprising applying to the unwanted plants an ester of a carboxylic acid agrochemical.
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Paragraph 0167; 0168; 0169
(2013/04/25)
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- Synthesis and herbicidal activities of sodium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates
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A series of sodium hydrogen 1-(substituted phenoxyacetoxy) alkylphosphonates was designed and synthesized. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against broadleaf weeds. Especially, 8f and 8g showed the best herbicidal activity against rape and amaranth with more than 95% inhibitory rate. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Long, Qingwu,Deng, Xiaoyan,Gao, Yujiao,Xie, Huayong,He, Hongwu,Peng, Hao
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p. 819 - 825
(2013/08/23)
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- Synthesis and herbicidal activities of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates
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A series of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates were designed and synthesized. All the title compounds were identified by IR, 1H NMR, and 31P NMR, some of them were further analyzed by MS and elemental analyses. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against broadleaf weeds. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Peng, Hao,Long, Qingwu,Deng, Xiaoyan,He, Hongwu
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p. 1868 - 1874
(2013/11/06)
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- Discovery, design and synthesis of novel potent and selective sphingosine-1-phosphate 4 receptor (S1P4-R) agonists
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High affinity and selective small molecule agonists of the S1P4 receptor (S1P4-R) may have significant therapeutic utility in diverse disease areas including autoimmune diseases, viral infections and thrombocytopenia. A high-throughput screening (HTS) of the Molecular Libraries-Small Molecule Repository library identified 3-(2-(2,4- dichlorophenoxy)ethoxy)-6-methyl-2-nitropyridine as a moderately potent and selective S1P4-R hit agonist. Design, synthesis and systematic structure-activity relationships study of the HTS-derived hit led to the development of novel potent S1P4-R agonists exquisitely selective over the remaining S1P1-3,5-Rs family members. Remarkably, the molecules herein reported provide novel pharmacological tools to decipher the biological function and assess the therapeutic utility of the S1P4-R.
- Guerrero, Miguel,Urbano, Mariangela,Zhao, Jian,Crisp, Melissa,Chase, Peter,Hodder, Peter,Schaeffer, Marie-Therese,Brown, Steven,Rosen, Hugh,Roberts, Edward
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scheme or table
p. 537 - 542
(2012/02/04)
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- Synthesis and biological activity of 2-Aryloxyacetylamino-2-Deoxy-D- Glucoses
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D-Glucosamine possesses extensive bioactivities including antibacterial, insecticidal and plant growth-regulating activities. A series of 2-aryloxyacetylamino-2-deoxy-D-glucoses have been synthesized by acylation of D-glucosamine with aryloxyacetyl chlorides and their plant growth-regulating activities were tested. The results show that these compounds bearing chlorine atom at para position of benzene ring have notable inhibiting activities against cotyledon rootage of cucumber which are comparable with that of 2,4-dichlorophenoxyacetic acid.
- Han, Liang,Zhu, Qiong-Yan,Jia, Jian-Hong,Li, Yu-Jin,Gao, Jian-Rong
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experimental part
p. 1223 - 1226
(2012/09/07)
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- Synthesis and herbicidal activity of 2-(Substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one
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A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by 1H NMR, 31P NMR, 13C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus, and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3, 2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.
- Wang, Wei,He, Hong-Wu,Zuo, Na,He, Hai-Feng,Peng, Hao,Tan, Xiao-Song
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experimental part
p. 7581 - 7587
(2012/10/08)
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- Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy) ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex
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On the basis of the previous work for optimization of O,O-diethyl α-(substituted phenoxyacetoxy)alkylphosphonates, further extensive syntheticmodifications were made to the substituents in alkylphosphonate and phenoxymoieties of the title compounds. New O,O-dimethyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compoundswere studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl α-(2,4- dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa, was found to be themost effective compound against broadleaf weeds and showed potential utility as herbicide.
- He, Hong-Wu,Yuan, Jun-Lin,Peng, Hao,Chen, Ting,Shen, Ping,Wan, Shu-Qing,Lee, Yanjun,Tan, Hong-Liang,He, Ya-Hui,He, Jun-Bo,Li, Yan
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scheme or table
p. 4801 - 4813
(2011/12/04)
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- Synthesis and biological evaluation of some substituted amino thiazole derivatives
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Condensation of acetophenone with thiourea in presence of halogen (Iodine) gives 2-amino-4-phenylthiazole (I). 2-Amino-4-phenyl-5-phenylazothizole (II) was prepared by coupling of phenyldiazonium chloride with 2-amino-4-phenylthiazole (I). A series of amide can be synthesized by treatment of appropriate substituted acid chlorides (III) with compound (II) using pyridine as solvent. All the synthesized compounds are characterized by the combination of elemental analysis and standard spectroscopic method. They are screened for anti-bacterial activity against Escherichia coli and Staphylococcus aureus as well as screened for antifungal activity against Aspergillus niger and Apergillus oryzae by cup plate method at 1μg/mL concentration in DMF. All the synthesized compounds showed moderate to good microbial activity.
- Prajapati,Modi, Vishal P.
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experimental part
p. 240 - 243
(2010/11/05)
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- Synthesis and antifungal activities of New pyrazole derivatives via 1,3-dipolar cycloaddition reaction
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A series of cycloadducts - pyrazoles via 1,3-dipolar cycloaddition reactions of generated nitrilimines with N-(4-chloro-2-fluorophenyl)maleimide were described. The novel compounds synthesized were characterized by 1H NMR, MS, and elemental analysis. The fungicidal tests showed that most of the title compounds exhibit significant fungicidal activities against Corynespora cassiicola.
- Zhang, Chuan-Yu,Liu, Xing-Hai,Wang, Bao-Lei,Wang, Su-Hua,Li, Zheng-Ming
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scheme or table
p. 489 - 493
(2011/02/21)
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- Design, synthesis and in vitro antibacterial/antifungal evaluation of novel 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid derivatives
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A series of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid (norfloxacin) derivatives were prepared according to the principle of combinating bioactive substructures and tested for their activities against five plant pathogenic bacteria and three fungi in vitro. The preliminary bioassays indicated that almost all synthesized target compounds retained the antibacterial activities of norfloxacin and had some antifungal activities as carboxylic acid amide compounds. The activities of compounds 1 and 22 against Xanthomonas oryzae were better than norfloxacin and all tested compounds had better antibacterial activities as compared to the agricultural streptomycin sulfate (a commercial bactericide) against X. oryzae, Xanthomonas axonopodis and Erwinia aroideae. Additionally, compounds 2 and 20 displayed good antifungal activities against Rhizoctonia solani and their inhibition of growth reached 83% and 94% respectively at the concentration of 200 mg/L.
- Yu, Zhiyi,Shi, Guanying,Sun, Qiu,Jin, Hong,Teng, Yun,Tao, Ke,Zhou, Guoping,Liu, Wei,Wen, Fang,Hou, Taiping
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experimental part
p. 4726 - 4733
(2010/01/06)
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- Synthesis and biological activity of α-oxo-2-pyridyl methyl phosphinates
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In an attempt to discover novel compounds with high activity and low toxicity, a series of new O,O-dimethyl-α-(substituted phenoxyacetoxy)-2- pyridyl methyl phosphinates, 5a-5h, have been designed and synthesized by the reaction of substituted phenoxyacetic chloride with 1-hydroxy-2-pyridyl methyl phosphinate, The structures of all new compounds were characterized by elementary analysis, IR, 1H NMR, and MS spectroscopies. The results of preliminary bioassay indicate that most of the target compounds have excellent inhibitory activities on barnyard grass and rape. Copyright Taylor & Francis Group, LLC.
- Wang, Tao,He, Hong Wu
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experimental part
p. 1884 - 1891
(2009/09/06)
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- Identification of anthranilic acid derivatives as a novel class of allosteric inhibitors of hepatitis C NS5B polymerase
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A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately 100-fold, yielding a series of potent and selective NS5B inhibitors with IC50 values as low as 10 nM. These compounds were also inhibitors of the HCV replicon in cultured HUH7 cells.
- Nittoli, Thomas,Curran, Kevin,Insaf, Shabana,DiGrandi, Martin,Orlowski, Mark,Chopra, Rajiv,Agarwal, Atul,Howe, Anita Y. M.,Prashad, Amar,Floyd, M. Brawner,Johnson, Bernard,Sutherland, Alan,Wheless, Karen,Feld, Boris,O'Connell, John,Mansour, Tarek S.,Bloom, Jonathan
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p. 2108 - 2116
(2008/02/06)
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- Synthesis of new plant growth regulator: N-(Fatty acid) O-aryloxyacetyl ethanolamine
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N-(Fatty acyl) O-aryloxyacetyl ethanolamines, prepared from N-acylethanolamine (NAE) and aryloxyacetic acid, were tested for plant growth regulating activity. Compared with N-stearoylethanolamine, most compounds exhibit improved plant growth stimulating activity. In particular, those with chlorine on aryl ring show better activity than 2,4-dichlorophenyloxyacetic acid in stimulating hypocotyls elongation of rape which indicates that chlorine on aryl ring appears significant. Moreover, these derivatives display improved solubility.
- Han, Liang,Gao, Jian-Rong,Li, Zheng-Ming,Zhang, Yun,Guo, Wei-Ming
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p. 3231 - 3234
(2008/02/07)
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- A novel class of potent influenza virus inhibitors: Polysubstituted acylthiourea and its fused heterocycle derivatives
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A series of polysubstituted and fused heterocycle derivatives of acylthiourea was prepared and the biological activity against influenza virus was evaluated. Of the analogues that demonstrated IC50s 0.1 μM, acylthiourea derivatives 16 and 50 were further investigated as candidates with the most potential for future development. The SAR of these compounds are discussed and they represent a novel class of highly potent and selective inhibitors of influenza virus.
- Sun, Chuanwen,Huang, Hai,Feng, Meiqing,Shi, Xunlong,Zhang, Xiaodong,Zhou, Pei
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p. 162 - 166
(2007/10/03)
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- Synthesis and evaluation of a new series of substituted acyl(thio)urea and thiadiazolo [2,3-a] pyrimidine derivatives as potent inhibitors of influenza virus neuraminidase
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A series of substituted acyl(thio)urea and 2H-1,2,4-thiadiazolo [2,3-a] pyrimidine derivatives were prepared and both of their cell culture and enzymatic activity toward influenza virus were tested. Their in vitro neuraminidase inhibitory activities were in good agreement with the corresponding activities in cultured cells and they were evaluated as potent neuraminidase inhibitors. Of the analogues that demonstrated IC50s 0.1 μM, 16 and 60 were further investigated as candidates with the most potential for future development. The molecular docking work of the representative compound was described to provide more insight into their mechanism of action and further rationalize the observations of this new series herein, which represents a novel class of highly potent and selective inhibitors of influenza virus.
- Sun, Chuanwen,Zhang, Xiaodong,Huang, Hai,Zhou, Pei
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p. 8574 - 8581
(2008/02/07)
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- New esters of vanillin and vanillal with some alkane- and arenecarboxylic acids
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Previously unknown esters were synthesized by the reaction of vanillin and vanillal with carboxylic acid chlorides. Pleiades Publishing, Inc., 2006.
- Dikusar
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p. 1035 - 1037
(2008/02/05)
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- Synthesis of esters of D, L-, D(+)-, and L(-)-camphor oximes: Structure-odor correlation
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Esters of D,L-, D(+)-, and L(-)-camphor oximes were synthesized, and the correlation between their structure and odor was examined.
- Dikusar,Zhukovskaya,Vyglazov
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p. 1982 - 1985
(2008/02/08)
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- Esters derived from vanillin and vanillal and aromatic and functionalized aliphatic carboxylic acids
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Reactions of vanillin and vanillal with aromatic and functionally substituted aliphatic carboxylic acid chlorides in the presence of pyridine afforded the corresponding previously unknown esters.
- Dikusar,Kozlov
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p. 992 - 996
(2007/10/03)
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- A convenient preparation of N-alkyl and N-arylamines by smiles rearrangement - Synthesis of analogues of diclofenac
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Smiles rearrangement of substituted aryloxyacetamides in which oxygen and nitrogen are separated by COCH2 group has been successful even when the aryloxy ring carries weak or no electron withdrawing group. Earlier reports of such reactions involved either strong electron withdrawing groups or a special catalyst. The diphenylamines thus obtained gave analogues of diclofenac in only one case.
- Wadia,Patil
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p. 2725 - 2736
(2007/10/03)
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- Synthesis of analogs of juvenile hormons proceeding from phenol derivatives
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New potential juvenoids, esters of alkenoic and alkadienoic acids with phenoxy-and phenoxy-phenoxyethanol were synthesized, and also esters of phenoxyacetic acid with alkenols amd alkadienols.
- Yamansarova,Kukovinets,Kukovinets,Zainullin,Galin,Kunakova,Zorin,Tolstikov
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p. 246 - 255
(2007/10/03)
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- Phase transfer catalyzed synthesis of amides and esters of 2,4- dichlorophenoxyacetic acid
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A convenient procedure is reported for the preparation of amides and esters via the reaction of 2,4-dichlorophenoxyacetyl chloride with amines or phenols under the condition of liquid-liquid phase transfer catalysis using polyethylene gtycol-600 as the catalyst. The products have been characterised on the basis of analytical and spectral (IR and H-NMR) data.
- Wei, Tai-Bao,Zhang, You-Ming,Xing, Hai-Yan
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p. 485 - 491
(2007/10/03)
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- Synthesis and dealkylation of 1 -(dichloro-phenoxyacetoxy) alkyl phosphonates
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Using the silylation procedure with chlorotrimethylsilane/sodium iodide followed by alcoholysis, 1-(dichlorophenoxy acetoxy)alkyl phosphonic acid dimethyl esters can be transformed into the parent phosphonic acids without influence on carboxylate ester group.
- He, Hongwu,Liu, Xufeng,Hu, Liming,Wang, Siquan,Liu, Zhaojie
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p. 633 - 636
(2007/10/03)
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- Synthesis of N- 2-pyrrolidinone as antimicrobial agent
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Several N- 2-pyrrolidinones have been synthesised and screened for their antibacterial and antifungal activities. their structures have been elucidated on the basis of elemental analysis and spectral data.
- Bhatt, P.,Srivastava, S. D.,Mehta, P.
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p. 514 - 516
(2007/10/03)
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- Agricultural polymers for controlled release of herbicide based on nitrogen-phosphorous polymers
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A novel synthesis of a polymeric herbicide system based on phosphorous-nitrogen containing polymer has been carried out by melt polycondensation of phenyl phosphonic dichloride with N-(2,4-dichlorophenoxyacetyl)diethanolamine 1 (2,4-D diolamide). The polymer is characterized by elemental analysis and IR spectroscopy. The release of 2,4-dichlorophenoxyacetic acid (2,4- D) from the polymer has also been investigated.
- Kenawy, El-Refale
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p. 886 - 889
(2007/10/03)
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