- Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi
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Abstract: A novel series of picarbutrazox-inspired oxadiazole hybrids was synthesized and the derivatives’ biological activity against phytopathogenic fungi was investigated. The molecules were designed by retaining the active fragment of tetrazolyl phenyloxime ether of lead compound picarbutrazox, while introducing the potentially active oxadiazole-derived fragment. Bioassay results revealed that some of the title compounds showed potent in vivo antifungal activities to control cucumber downy mildew. Therefore, this novel oxadiazole phenyloxadiazole derivative can be used as a potential antifungal agent to control cucumber downy mildew and other phytopathogenic fungi for crop protection. Graphic abstract: [Figure not available: see fulltext.].
- Li, Yitao,Yao, Wenqiang,Lin, Jian,Gao, Guoliang,Huang, Chang,Wu, Yang
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p. 121 - 135
(2021/01/05)
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- Synthesis, fungicidal activity, and 3D-QSAR of tetrazole derivatives containing phenyloxadiazole moieties
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In an effort to discover new agents with good fungicidal activities against CDM (cucumber downy mildew), a series of tetrazole derivatives containing phenyloxadiazole moieties were designed and synthesized. The EC50 values for fungicidal activities against CDM were determined. Bioassay results indicated that most synthesized compounds exhibited potential in vivo fungicidal activity against CDM. A CoMFA (comparative molecular field analysis) model based on the bioactivity was developed to identify some primary structural quality for the efficiency. The values of q2 and r2 for the established model were 0.791 and 0.982 respectively, which reliability and predict abilities were verified. Three analogues (q3, q4, q5) were designed and synthesized based on the model. All these compounds exhibited significant fungicidal activity on CDM with the EC50 of 1.43, 1.52, 1.77 mg·L?1. This work could provide a useful instruction for the further structure optimization.
- Li, Yi-Tao,Yao, Wen-Qiang,Zhou, Si,Xu, Jun-Xing,Lu, Hui,Lin, Jian,Hu, Xiao-Yun,Zhang, Shao-Kai
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supporting information
(2021/01/11)
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- Novel oxime derivative as well as preparation method and application thereof
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The invention relates to a novel oxime derivative and a preparation method and application thereof, the novel oxime derivative has a structure as shown in formula (I), Q is optionally substituted phenyl, T is C1-6 alkyl substituted tetrazolyl, and A is th
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Paragraph 0122-0124
(2021/06/22)
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- Diphenyl ether-substituted oxime derivative and application thereof in agriculture
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The invention relates to a diphenyl ether-substituted oxime derivative and application thereof in agriculture, the diphenyl ether-substituted oxime derivative has a structure as shown in formula (I), Q is phenyl, T is tetrazolyl, L is 1, 2, 4-oxadiazolyl
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Paragraph 0126-0127
(2021/06/22)
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- Oxime derivative and application thereof in agriculture
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The invention relates to an oxime derivative and an application thereof in agriculture, the oxime derivative has a structure as shown in formula (I), and Ra, Rb, Rc, Rd and Re are respectively and independently hydrogen, halogen and the like; T is tetrazolyl, M is 1, 3, 4-oxadiazolyl, 1, 2, 4-oxadiazolyl, 1, 3, 4-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1, 2, 4-triazolyl, 1, 3, 4-triazolyl and the like; A is phenyl or phenyl optionally substituted by 1, 2, 3, 4 or 5 selected from halogen, cyano, nitro, hydroxyl, C1-6 alkyl, C1-6 alkoxy, halogenated C1-6 alkyl and the like; the oxime derivative disclosed by the invention has the advantages of small dosage and high control effect on cucumber downy mildew, and can be further developed to be applied as a bactericide.
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Paragraph 0151-0152
(2021/06/22)
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- Amine-Mediated Bond Cleavage in Oxidized Lignin Models
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Introducing amines/ammonia into lignin cracking will allow novel bond cleavage pathways. Herein, a method of amines/ammonia-mediated bond cleavage in oxidized lignin β-O-4 models was studied using a copper catalyst at room temperature, demonstrating the effect of the amine source on the selectivity of products. For primary and secondary aliphatic amines, lignin ketone models underwent oxidative Cα?Cβ bond cleavage and Cα?N bond formation to generate aromatic amides. For ammonia, the competition between oxygen and ammonia determined the selectivity between Cα?N and Cβ?N bond formation, generating amides and α-keto amides, respectively. For tertiary amines, the lignin models underwent oxidative Cα?Cβ bond cleavage to benzoic acids. Control experiments indicated that amines act as nucleophiles attacking at the Cα or Cβ position of the oxidized β-O-4 linkage to be cleaved. This study represents a novel example that the breakage of oxidized lignin model can be regulated by amines with a copper catalyst.
- Li, Hongji,Liu, Meijiang,Liu, Huifang,Luo, Nengchao,Zhang, Chaofeng,Wang, Feng
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p. 4660 - 4665
(2020/07/04)
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- 1, 3, 4-oxadiazole oxime derivative as well as preparation method and application thereof
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The invention relates to a 1, 3, 4-oxadiazole oxime derivative as well as a preparation method and application thereof. Specifically, the present invention relates to a 1, 3, 4-oxadiazole oxime derivative represented by a formula (I) or a stereoisomer, nitrogen oxide or salt thereof represented by a formula (I), and a preparation method of the 1, 3, 4-oxadiazole oxime derivative, uses of the 1, 3,4-oxadiazole oxime derivative and the stereoisomer, nitrogen oxide or salt thereof as bactericides in agriculture, and forms of bactericide compositions thereof, as well as methods of controlling plant disease using these compounds or compositions; and A, R1, Ra, Rb, Rc, Rd, Re, T and x have the meanings described in the invention.
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Paragraph 0121-0122
(2020/12/31)
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- Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
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Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
- Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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p. 11823 - 11838
(2019/10/02)
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- UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution
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Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.
- Li, Jianhui,He, Shaopo,Zhang, Kuan,Quan, Ziyi,Shan, Qiheng,Sun, Zhongliang,Wang, Bo
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p. 4868 - 4873
(2018/10/15)
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- Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides
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A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100?000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism.
- Gu, Guoxian,Yang, Tilong,Yu, Ouran,Qian, Hua,Wang, Jiang,Wen, Jialin,Dang, Li,Zhang, Xumu
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p. 5920 - 5923
(2017/11/10)
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- nBu4NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety
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Presented here is the first example of synthesizing an array of primary-, secondary-, and tertiary-α-ketoamides with a non-metal catalyst nBu4NI from methyl ketones and inexpensive readily available amine/ammonium salts; the reactions proceeded smoothly under mild conditions, TBHP was used as an oxidant and the corresponding α-ketoamides were afforded in moderate to excellent yields.
- Wang, Dan,Zhang, Kuan,Jia, Luhan,Zhang, Danting,Zhang, Yue,Cheng, Yujia,Lin, Chang,Wang, Bo
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p. 3427 - 3434
(2017/04/24)
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- Convenient method for the preparation of secondary α-ketoamides via aminocarbonylation of acid chlorides with carbamoylsilane
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The convenient transformation of acid chlorides into corresponding secondary α-ketoamides by the aminocarbonylation of acid chlorides with N-methoxymethyl-N-methylcarbamoyl(trimethyl)silane is described. The use of carbamoylsilane containing methoxymethyl
- Ma, Fei,Liu, Hui,Chen, Jianxin
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p. 5246 - 5250
(2016/11/11)
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- A purifying crude formamide-methyl benzoyl N the method of
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The invention relates to the field of organic synthesis, and discloses a method for purifying a N-methylphenacyl formamide crude product. The method comprises the step that under a solution condition, the N-methylphenacyl formamide crude product is in fir
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Paragraph 0052; 0058-0061; 0064
(2018/02/04)
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- Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives
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A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.
- Liu, Le,Du, Liang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 5772 - 5775
(2015/02/19)
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- Cu(ii)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides
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CuBr2-catalyzed decarboxylative acylation of the acyl C-H of N-monosubstituted and N,N-disubstituted formamides with α-oxocarboxylic acids leading to α-ketoamides was developed, which generated the corresponding products in good yields. The Royal Society of Chemistry 2013.
- Li, Dengke,Wang, Min,Liu, Jie,Zhao, Qiong,Wang, Lei
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supporting information
p. 3640 - 3642
(2013/05/21)
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- Direct use of formamides as amino group sources via C-N bond cleavage: A catalytic oxidative synthesis of α-ketoamides from acetophenones and formamides under metal-free conditions
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An efficient and direct use of formamides as amino group sources for the synthesis of α-ketoamides was developed under metal-free conditions. The reaction was based on the oxidative coupling of acetophenones with formamides and generated the desired products in good yields in the presence of t-BuOOH/I2/PhCO2H.
- Zhao, Qiong,Miao, Tao,Zhang, Xiaobin,Zhou, Wei,Wang, Lei
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p. 1867 - 1873
(2013/04/10)
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- Simplified procedure for TEMPO-catalyzed oxidation: Selective oxidation of alcohols, α-hydroxy esters, and amides using TEMPO and calcium hypochlorite
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A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl)2]. This simplified method does not require any transition metals, acids, or bases and demonstrates controlled and selective oxidation of structurally diverse alcohols, affording moderate to excellent yields at room temperature.
- Reddy, Sabbasani Rajasekhara,Stella, Selvaraj,Chadha, Anju
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experimental part
p. 3493 - 3503
(2012/09/22)
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- Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330
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Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.
- Stella, Selvaraj,Chadha, Anju
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p. 345 - 352
(2013/01/15)
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- PROCESS FOR PREPARATION OF 1-ALKYL-5-BENZOYL-1H-TETRAZOLE DERIVATIVES
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The present invention provides a process for preparation of 1-alkyl-5-benzoyl-1H-tetrazole derivative including a step 1 of reacting a ketoamide derivative represented by formula (I) (in formula (I), A represents a halogen atom or the like; n represents a
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Page/Page column 8
(2012/01/14)
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- Copper-catalyzed synthesis of azaspirocyclohexadienones from ∝-azido- N -arylamides under an oxygen atmosphere
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A copper-catalyzed reaction of ∝-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from ∝-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C-O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O2 was found to be incorporated into the cyclohexadienone moiety.
- Chiba, Shunsuke,Zhang, Line,Lee, Jian-Yuan
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supporting information; experimental part
p. 7266 - 7267
(2010/08/05)
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- α-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
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N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide α-keto amides 2-12 in 28-90percent yields.The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84percent yields.A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed.Several control experiments were carried out to support the proposed mechanism.
- Sibi, Mukund P.,Marvin, Mali,Sharma, Rajiv
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p. 5016 - 5023
(2007/10/03)
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- N,N'-Dimethoxy-N,N'-dimethylethanediamide: A useful α-oxo-N-methoxy-N-methylamide and 1,2-diketone synthon
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N,N'-Dimethoxy-N,N'-dimethylethanediamide on treatment with one to two equivalents of alkyl, aryl, and benzyl Grignard reagents provide α-oxo-N-methoxy-N-methylamides in good to excellent yields and on reaction with excess aryllithiums furnish moderate to good yields of symmetrical 1,2-diarylketones.
- Sibi,Sharma,Paulson
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p. 1941 - 1944
(2007/10/02)
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