73286-67-6Relevant articles and documents
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
, (2021/05/04)
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.
Organoselenium- and Proton-Mediated Cyclization Reactions of Allylic Amides and Thioamides. Syntheses of 2-Oxazolines and 2-Thiazolines
Engman, Lars
, p. 3425 - 3430 (2007/10/02)
A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position.In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization.The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline.Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride.This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring.Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.
New Allylation Reaction using Allylmetal (Group IVb) Compounds: Synthesis of N-Allylamides
Ochiai, Masahito,Tada, Shin-Ichi,Arimoto, Masao,Fujita, Eiichi
, p. 2836 - 2839 (2007/10/02)
Reaction of allylsilanes 1a and 1d or allylstannane 1b with thallium(III) salts in nitriles such as acetonitrile, acrylonitrile, propionitrile, and benzonitrile afforded the corresponding N-allylamides.Thus, umpolung of reactivity of allylsilane and allylstannane has been established.Keywords-umpolung of reactivity; allylsilane; allylstannane; N-allylamide; thallium(III) salt; nitrile
