64075-37-2Relevant academic research and scientific papers
New lead discovery of herbicide safener for metolachlor based on a scaffold-hopping strategy
Deng, Xile,Zheng, Wenna,Zhan, Qingcai,Deng, Yanan,Zhou, Yong,Bai, Lianyang
, (2020)
The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of the existing herbicides in the field. Sanshools, which are well known as spices, are N-alkyl substituted compounds extracted from the Zanthoxylum species and have several essential physiological and pharmacological functions. Sanshools display excellent safener activity for the herbicide metolachlor in rice seedlings. However, the high cost of sanshools extraction and difficulties in the synthesis of their complicated chemical structures limit their utilization in agricultural fields. Thus, the present study designed and synthesized various N-alkyl amide derivatives via the scaffold-hopping strategy to solve the challenge of complicated structures and find novel potential safeners for the herbicide metolachlor. In total, 33 N-alkyl amide derivatives (2a–k, 3a–k, and 4a–k) were synthesized using amines and saturated and unsaturated fatty acids as starting materials through acylation and condensation. The identity of all the target compounds was well confirmed by1H-NMR,13C-NMR, and high-resolution mass spectrometry (HRMS). The primary evaluation of safener activities for the compounds by the agar method indicated that most of the target compounds could protect rice seedlings from injury caused by metolachlor. Notably, compounds 2k and 4k displayed excellent herbicide safener activities on plant height and demonstrated relatively similar activities to the commercialized compound dichlormid. Moreover, we showed that compounds 2k and 4k had higher glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and polyphenol oxidase (PPO) activities in rice seedlings, compared to the metolachlor treatment. In particular, 2k and 4k are safer for aquatic organisms than dichlormid. Results from the current work exhibit that compounds 2k and 4k have excellent crop safener activities toward rice and can, thus, be promising candidates for further structural optimization in rice protection.
ALKAMIDE COMPOUNDS AND USES THEREOF
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Page/Page column 75; 77; 80, (2019/04/27)
The present disclosure relates to alkamide compounds and compositions for treating allergic diseases, pain, or itch.
Enzymatic Method for N-Acyl Homoserine Lactones Synthesis Using Immobilized Candida antarctica Lipase
Vázquez-Martínez, Juan,Nieto-álvarez, Edgar,Ramírez-Chávez, Enrique,Molina-Torres, Jorge
, p. 62 - 67 (2017/12/18)
Abstract: An enzymatic method to produce N-acyl homoserine lactones (AHLs) is described. This report represents the first example of the synthesis of bioactive AHLs using immobilized Candida antarctica lipase as the catalyst. The reaction yields, evaluate
Synthesis and biological evaluation of a series of fatty acid amides from Echinacea
Moazami, Yasamin,Gulledge, Travis V.,Laster, Scott M.,Pierce, Joshua G.
supporting information, p. 3091 - 3094 (2015/07/08)
Abstract Alkylamides are lipophilic constituents of Echinacea and possess numerous biological activities. Although significant effort has been focused on the study of crude Echinacea extracts, very little is known regarding the activities of the individual constituents that make up these herbal treatments. Herein we explore the SAR of simple alkylamides found in Echinacea extracts with respect to their ability to decrease the production of the pro-inflammatory mediator TNF-α. Our results have revealed the key structural requirements for activity and provide lead compounds for further investigation of these poorly understood molecules.
Intermolecular hydrogen bonding between N-substituted caproamides and tetrahydrofuran
Jovic,Nikolic,Hollo
, p. 431 - 436 (2013/07/27)
The results are reported of a study of hydrogen bonding between various N-substituted caproamides and tetrahydrofuran as an O-electron donor by means of FTIR spectroscopy. The spectroscopic characteristics for N-H.O hydrogen bonded complexes are given. The B3LYP functional with 6-31G**basis set has been used to calculate the structural parameters of the studied hydrogen bonded complexes. It can be assumed that both inductive and steric effects play an important role in the stability of these hydrogen bonded complexes.
Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides
Rossi, Steven A.,Shimkin, Kirk W.,Xu, Qun,Mori-Quiroz, Luis M.,Watson, Donald A.
supporting information, p. 2314 - 2317 (2013/06/05)
For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides.
