- METHODS OF CONTROLLING CROP PESTS USING AROMATIC AMIDE INSECT REPELLENTS, METHODS OF MAKING AROMATIC AMIDE INSECT REPELLENTS, AND NOVEL AROMATIC AMIDE INSECT REPELLENTS
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Methods of protecting fruit crops from flying insect pests and of repelling flying insects using aromatic amide compounds are disclosed. The methods apply the compounds to various surfaces, such as the fruit crops, the ground or structures adjacent to the fruit crops, or an object, article, human skin or animal. The compounds have the formula RxC6Hy—C(═O)—N(Cy), where RxC6Hy is a substituted phenyl group, each R group is independently C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, C1-C4 alkoxy, C6-C10 aryloxy, halogen, nitro, cyano, cyanate, isocyanate, nitroso, C1-C4 alkylthio, phenylthio, (halogen-substituted) C1-C4 alkylsulfonyl, phenylsulfonyl, tolylsulfonyl, amino, mono- or di-C1-C4 alkylamino, diphenylamino, di-C1-C4 alkylamido, formyl, C2-C7 acyl, or C1-C6 alkoxycarbonyl; x is an integer of 1 to 5; x+y=5; Cy is a C2-C8 (substituted) alkadiyl, a C4-C6 (substituted) alkenediyl, or a (substituted) diyl of the formula —(CH2CH2)—O—(CH2CH2)—, —(CH2CH2)—NR′—(CH2CH2)— or —(CH2CH2)—S—(CH2CH2)— that, along with the amide N atom, forms a non-aromatic cyclic group; and R′ is C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, or (substituted) benzyl.
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Paragraph 0068-0069
(2022/03/18)
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- Synthesis of Ag/g-C3N4Composite as Highly Efficient Visible-Light Photocatalyst for Oxidative Amidation of Aromatic Aldehydes
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In this contribution, an Ag/g-C3N4nanocomposite was synthesized and utilized as highly efficient and green photocatalyst for organic reactions under visible light irradiation. A layered, porous g-C3N4was synthes
- Wang, Lingling,Yu, Min,Wu, Chaolong,Deng, Nan,Wang, Chao,Yao, Xiaoquan
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p. 2631 - 2641
(2016/08/31)
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- Supported cobalt oxide nanoparticles as efficient catalyst in esterification and amidation reactions
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Co/SBA-15 nanoparticle catalysts (CoNP) were prepared using a commonly adapted synthetic route and then utilised for esterification and amidation reactions using aromatic and linear chain compounds for the production of long chain esters and amides. The study shows that the use of CoNP catalysts favours the use of aromatic reactants with electron donating substituents specifically in the para position. For the amidation reaction, good to excellent yields were obtained demonstrating tolerance towards differently substituted aromatic compounds. Overall, the synthesized catalysts proved to be efficient and highly versatile, and recyclable under the investigated conditions.
- Rajabi, Fatemeh,Raessi, Mojdeh,Arancon, Rick A.D.,Saidi, Mohammad Reza,Luque, Rafael
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p. 122 - 126
(2015/01/09)
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- Kinetic study on aminolysis of y-substituted-phenyl x-substituted- benzoates: Effects of substituents x and y on reactivity and reaction mechanism
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A kinetic study on aminolysis of 2-chloro-4-nitrophenyl X-substituted-benzoates (2a-k) in 80 mol % H2O/20 mol % DMSO at 25.0 oC is reported. The Bronsted-type plot for the reactions of 2-chloro-4-nitrophenyl benzoate (2g) with a series of cyclic secondary amines curves downward (e.g., β1 = 0.25, β2 = 0.85 and pKa o = 10.3), which is typical of reactions reported to proceed through a stepwise mechanism with a change in ratedetermining step (RDS). The Hammett plot for the reactions of 2a-k with piperidine consists of two intersecting straight lines, while the corresponding Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 1.15 and r = 0.59. Thus, it has been concluded that the nonlinear Hammett plot is not due to a change in RDS but is caused by stabilization of substrates through resonance interactions between the electron-donating substituent and the C=O bond. Substrates possessing a substituent at the 2-position of the leaving aryloxide deviate negatively from the curved Bronsted-type plot for the reactions of Y-substituted-phenyl benzoates (3ai), implying that the steric hindrance exerted by the substituent at the 2-position is an important factor which governs the reactivity of Y-substituted-phenyl benzoates.
- Jeon, Seong Hoon,Kim, Hyun Soo,Han, Young Joon,Kim, Min-Young,Um, Ik-Hwan
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p. 471 - 476
(2014/03/21)
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- Kinetic study on aminolysis of 2-chloro-4-nitrophenyl x-substituted-benzoates in acetonitrile and in H2O Containing 20mol% DMSO: Effects of medium and substituent X on reactivity and reaction mechanism
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Second-order rate constants for reactions of 2-chloro-4-nitrophenyl X-substituted-benzoates 1a-1j with a series of cyclic secondary amines in MeCN have been measured. Comparison of the kinetic results with those reported previously for the corresponding reactions carried out in H2O containing 20 mol % DMSO has revealed that amines are less reactive in MeCN. The Bronsted-type plot for the aminolysis of 2-chloro-4-nitrophenyl benzoate (1f) in MeCN is linear with βnuc= 0.64, which is in contrast to the curved Bronsted-type plot reported for the reaction performed in the H2O-DMSO misxture. The Hammett plot for the reactions of 1a-1j with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX= 1.22 and r = 0.60, indicating that the nonlinear Hammett plot is not due to a change in rate-determining step but is caused by stabilization of substrates possessing an electron-donating substituent through resonance interactions between the substituent and the carbonyl functionality. It has been concluded that medium change from the H2O-DMSO mixture to MeCN forces the aminolysis of 1a-1j to proceed through a concerted mechanism by destabilizing the zwitterionic tetrahedral intermediate (T±).
- Kim, Ha-Ram,Yoon, Jung Hwan,Kim, Min-Young,Um, Ik-Hwan
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supporting information
p. 922 - 927
(2015/02/19)
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- Comparison of aminolysis of 2-pyridyl and 4-pyridyl x-substituted benzoates in acetonitrile: Evidence for a concerted mechanism involving a cyclic transition state
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A kinetic study on reactions of 2-pyridyl X-substituted benzoates (6a-i) with a series of cyclic secondary amines in MeCN is reported. The Hammett plot for the reaction of 6a-i with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 1.28 and r = 0.63, indicating that the nonlinear Hammett plot is not caused by a change in the rate-determining step but rather by resonance stabilization of substrates possessing an electron-donating group (EDG) in the benzoyl moiety. The Bronsted-type plots are linear with βnuc = 0.59 ± 0.02, which is typical of reactions reported to proceed through a concerted mechanism. A cyclic transition state (TS), which forces the reaction to proceed through a concerted mechanism, is proposed. The deuterium kinetic isotope effect of 1.3 ± 0.1 is consistent with the proposed mechanism. Analysis of activation parameters reveals that ΔH? increases linearly as the substituent X changes from an electron-withdrawing group (EWG) to an EDG, while TΔS ? remains nearly constant with a large negative value. The constant TΔS? value further supports the proposal that the reaction proceeds through a concerted mechanism with a cyclic TS.
- Um, Ik-Hwan,Bae, Ae-Ri,Um, Tae-Il
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p. 1206 - 1212
(2014/03/21)
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- Metal-free one-pot synthesis of amides using graphene oxide as an efficient catalyst
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Graphene oxide (GO), exhibiting a high degree of oxygen functionality and various structural defects, was found to be a highly efficient and cost effective carbocatalyst for the one-pot base-free synthesis of amides from aromatic aldehydes and secondary amine. The chemical and structural features of GO, as probed by FTIR, Raman, XRD and HRTEM analyses, were discussed to understand the catalytic mechanism for the synthesis of amides. The present method obviates the use of transition metal catalysts and needs shorter reaction time. This journal is
- Kumari, Shweta,Shekhar, Amiya,Mungse, Harshal P.,Khatri, Om P.,Pathak, Devendra D.
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p. 41690 - 41695
(2014/12/11)
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- Metal-free one-pot synthesis of amides using graphene oxide as an efficient catalyst
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Graphene oxide (GO), exhibiting a high degree of oxygen functionality and various structural defects, was found to be a highly efficient and cost effective carbocatalyst for the one-pot base-free synthesis of amides from aromatic aldehydes and secondary amine. The chemical and structural features of GO, as probed by FTIR, Raman, XRD and HRTEM analyses, were discussed to understand the catalytic mechanism for the synthesis of amides. The present method obviates the use of transition metal catalysts and needs shorter reaction time. This journal is
- Kumari, Shweta,Shekhar, Amiya,Mungse, Harshal P.,Khatri, Om P.,Pathak, Devendra D.
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p. 41690 - 41695
(2015/05/20)
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- Gold-catalyzed amide synthesis from aldehydes and amines in aqueous medium
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An efficient gold-catalyzed amide synthesis from aldehydes and amines in aqueous medium under mild reaction conditions has been developed.
- Li, Gai-Li,Kung, Karen Ka-Yan,Wong, Man-Kin
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supporting information; experimental part
p. 4112 - 4114
(2012/06/16)
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- Aerobic oxidative amidation of aromatic and cinnamic aldehydes with secondary amines by CuI/2-pyridonate catalytic system
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A simple and convenient CuI/2-pyridonate catalytic system for the oxidative amidation of aldehydes with secondary amines has been developed. With this system, a variety of useful arylamides have been synthesized in moderate to good yields in the presence of small amount of copper catalyst and the pyridonate ligand, generating only water as a coproduct. Synthesis of cinnamamides was also achieved by the reactions of cinnamaldehydes with secondary amines in moderate yields. Air was successfully employed as a green oxidant in this catalytic system, achieving a safe and atom-efficient system for the synthesis of amides.
- Zhu, Mingwen,Fujita, Ken-Ichi,Yamaguchi, Ryohei
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p. 9102 - 9109,8
(2012/12/11)
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- Kinetic study on aminolysis of 4-pyridyl X-substituted benzoates: Effect of substituent X on reactivity and reaction mechanism
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A kinetic study is reported for nucleophilic substitution reactions of 4-pyridyl X-substituted benzoates 7a-e with a series of alicyclic secondary amines in H2O. The Bronsted-type plot for the reactions of 4-pyridyl benzoate 7c is linear with βnuc = 0.71. The corresponding reactions of 2-pyridyl benzoate 6, which is less reactive than 7c, resulted in also a linear Bronsted-type plot with βnuc = 0.77. The fact that the more reactive 7c results in a smaller βnuc value appears to be in accord with the reactivity- selectivity principle. The aminolysis of 7c has been suggested to proceed through a stepwise mechanism in which breakdown of the intermediate is the rate-determining step (RDS). The Hammett plot for the reactions of 7a-e with piperidine consists of two intersecting straight lines, i.e., ρX = 1.47 for substrates possessing an electron-donating group (EDG) and ρX = 0.91 for those possessing an electron-withdrawing group (EWG). In contrast, the corresponding Yukawa- Tsuno plot exhibits excellent linear correlation with ρX = 0.79 and r = 0.56. Thus, it has been concluded that the nonlinear Hammett plot is not due to a change in the RDS but is caused by stabilization of the ground state of the substrates possessing an EDG through resonance interaction between the EDG and the C=O bond of the substrates.
- Lee, Jong Pal,Bae, Ae Ri,Um, Ik-Hwan
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experimental part
p. 1907 - 1911
(2012/01/14)
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