Synthesis and Herbicidal Activities of 2-Ethoxyethyl 2-Cyano-3-(substituted)acrylates

钟世华,; 王春凤,; 宋青霞,; 范明亮,; 刘兵玉,; 危冬梅,; 刘建兵,

doi:10.6023/cjoc201404020

Cited by 5 publications

(4 citation statements)

References 4 publications

(6 reference statements)

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“…With primary aromatic amines as nucleophiles, − the desired, more thermodynamically stable compounds 9 were obtained in high yields with the amino group cis to the alkylcarbonyl moiety of 9 due to formation of an intramolecular hydrogen bond between NH and the oxygen of carbonyl group (Scheme ). Products 9c , 9d , and 9i showed good selectivity and activity against dicotyledonous weeds .…”

Section: General Methods For Synthesis Of Functionalized Ketene Ns-ac...mentioning

confidence: 99%

Chemistry of Ketene N,S-Acetals: An Overview

et al. 2016

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Push-pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push-pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of ketene N,S-acetals, especially, in recent years. This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals.

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Section: General Methods For Synthesis Of Functionalized Ketene Ns-ac...mentioning

confidence: 99%

Chemistry of Ketene N,S-Acetals: An Overview

et al. 2016

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“…Besides the 3-phenylamino-and 3-alkylamino-2-cyanoacrylates, some 2-cyanoacrylates bearing other types of substituent, such as a hydrazino group 80 (general structure XXIII in Figure 20) and arylureido 81 (general structure XXIV), have also been synthesized. However, these compounds were found to have low herbicidal activities.…”

Section: ■ Herbicidal 2-cyanoacrylatesmentioning

confidence: 99%

Recent Advances in the Pesticide Activities of 2-Cyanoacrylate Derivatives

Liu

Wang

2021

J. Agric. Food Chem.

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2-Cyanoacrylates are a unique class of compounds with high photosystem II electron transport inhibitory activity. Through the in-depth study of molecular design, synthesis, biological activity, structure−activity relationship, and action mechanism, a large number of 2-cyanoacrylate derivatives with excellent herbicidal activity were found. In addition, 2-cyanoacrylate derivatives with different substituents have also been found to have good fungicidal or anti-plant virus activities. To further guide the design and development of new pesticide candidates, the representative research work of 2-cyanoacrylate derivatives with herbicidal, fungicidal, and anti-plant virus activities was reviewed.

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“…In recent years, 2-cyanoacrylatesplay a vital role in pesticidal and medicinal fields. Many 2-cyanoacrylate-based compounds have attracted intense attention for different bioactivities containing insecticidal [ 1 , 2 ], herbicidal [ 3 , 4 , 5 ], fungicidal [ 6 ], plant growth regulatory [ 7 ], and antitumor activity [ 8 ]. For example, NK-9717 ( Figure 1 ), a potent herbicide owning 2-cyanoacrylate moiety, displayed wonderful herbicidal properties against some weeds such as Brassica campestris and Amaranthus retroflexus [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety

et al. 2023

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To develop novel 2-cyanoacrylate derivatives with potential bioactivity, a number of 2-cyanoacrylate compounds, including substituted pyrazole or 1,2,3-triazole ring, were designed, prepared, and structurally detected by 1H NMR, 13C NMR, and elemental analysis. The biological assessment displayed that some designed compounds had significant herbicidal activities against Brassica juncea, Chenopodium serotinum, Rumex acetosa, Alopecurus aequalis, Polypogon fugax, and Poa annua at a dosage of 1500 g/ha. Furthermore, some derivatives still expressed satisfactory herbicidal activities against Brassica juncea, Chenopodium serotinum, and Rumex acetosa when the dosage was lowered to 150 g/ha, especially the inhibitory effects of compounds 9a, 9d, 9f, 9i, 10a, 10b, 10e, and 10n against Brassica juncea were all over 80%, compounds 9d, 9f, 9g, 9h, 9i, 10h, 10i, 10m, 10n, and 10o possessed more than 70% inhibition rates against Chenopodium serotinum, and compound 9d indicated 70% herbicidal activity against Rumex acetosa. These results provided an important basis for further design and discovery of biologically active 2-cyanoacrylate compounds.

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Synthesis and Herbicidal Activities of 2-Ethoxyethyl 2-Cyano-3-(substituted)acrylates

Cited by 5 publications

References 4 publications

Chemistry of Ketene N,S-Acetals: An Overview

Chemistry of Ketene N,S-Acetals: An Overview

Recent Advances in the Pesticide Activities of 2-Cyanoacrylate Derivatives

Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety

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