Design, synthesis and nematicidal activitives of trifluorobutene amide derivatives against Meloidogyne incognita

Yang, Haiping; Zhang, Ruifeng; Li, Zhong; Maienfisch, Peter; Xu, Xiaoyong

doi:10.1016/j.bmcl.2021.127917

Cited by 9 publications

(11 citation statements)

References 21 publications

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“…The compound bearing a pyrazine ring (A8) exhibited the best activity, and the inhibition rate reached 56.3% at 5.0 mg L −1 in the matrix. 75 Our results demonstrated that bioisosteric replacement of sulfone by amide was a successful method and achieved a potential active compound. Divalent isosteres, ring equivalents, and scaffold hopping were also applied.…”

Section: Amide Replacement Based On Bioisosterismmentioning

confidence: 63%

“…A preliminary in vitro activity test showed that 9 compounds among the 19 compounds containing different aromatic rings or heterocycles ( A – A18 ) exhibited mortality higher than 85.0% against M. incognita at the concentration of 40 mg L –1 after 72 h of exposure (LC 50/72 h ) . The compound ( A8 ) containing a pyrazine ring gave a LC 50/72 h value of 2.02 mg L –1 and was identified as the best active analogue among compounds A – A18 , ahead of 5-chlorothiazole ( A1 ) and pyrimidine ring ( A9 ) analogues, which gave LC 50/72 h values of 3.03 and 3.22 mg L –1 , respectively.…”

Section: Novel Bioisosteric Design Strategies For the Identification ...mentioning

confidence: 99%

“…The activity in the matrix test was well in line with the sand test results, except for compound A11 , which expressed a 94.2% inhibition rate in sand but was almost inactive in the matrix test. The compound bearing a pyrazine ring ( A8 ) exhibited the best activity, and the inhibition rate reached 56.3% at 5.0 mg L –1 in the matrix …”

Section: Novel Bioisosteric Design Strategies For the Identification ...mentioning

confidence: 99%

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Bioisosterism and Scaffold Hopping in Modern Nematicide Research

Cao

Yang

Liu

et al. 2022

J. Agric. Food Chem.

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The application of agrochemicals is critical to global food safety. Nowadays, environmentally friendly green agrochemicals are the trend in field crop protection. The research and development of nematicides absorbed more attention as a typical representation of agrochemicals. This review describes the origin of recently commercialized nematicides, the application of bioisosterism and scaffold hopping in the discovery and optimization of agrochemicals, especially nematicides, and novel bioisosteric design strategies for the identification of fluensulfone analogues. Pesticide repurposing, high-throughput screening, computer-aided drug design, and incorporation of known pharmacophoric fragments have been the most successful approach for the discovery of new nematicides. As outlined, the strategies of bioisosteric replacements and scaffold hopping have been very successful approaches in the search for new nematicides for sustainable crop protection. In the exploration of novel fluensulfone analogues with nematicidal activity, bioisosteric replacement of sulfone by amide, chain extension by insertion of a methylene group, and reversal of the amide group have proven to be successful approaches and yielded new and highly active fluensulfone analogues. These attempts might result in compounds with an optimal balance of steric, hydrophobic, electronic, and hydrogen-bonding properties and contribute to deal with the complex problem during the research and development of new nematicides. Further ideas are also put forward to provide new approaches for the molecular design of nematicides.

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Section: Amide Replacement Based On Bioisosterismmentioning

confidence: 63%

Section: Novel Bioisosteric Design Strategies For the Identification ...mentioning

confidence: 99%

Section: Novel Bioisosteric Design Strategies For the Identification ...mentioning

confidence: 99%

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Bioisosterism and Scaffold Hopping in Modern Nematicide Research

Cao

Yang

Liu

et al. 2022

J. Agric. Food Chem.

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“…The in vivo activity of compound 16 (Figure 5) against M. incognita was 80% at 8 mg/L [54]. Compound 17 shows good nematicidal activity against B. xylophilus was 64% at 10 mg/L [55]. The in vivo activity of compound 18 against M. incognita was >87% at 40 mg/L, and the amide group replaced the sulfone group to bring about a change in activity [56].…”

Section: Thiazolementioning

confidence: 99%

Recent research progress of heterocyclic nematicidal active compounds

Wang

Luo

Chen

et al. 2023

Journal of Heterocyclic Chem

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Plant‐parasitic nematodes cause huge economic losses of $ 157 billion to world agriculture annually. Long‐term use of traditional nematicides can lead to increased resistance of nematode and reduced control effectiveness. New effective and safe nematicides are needed to replace the organophosphorus and carbamate. Heterocyclic compounds play an important role in nematicide discovery. For example, the new nematicides fluenesulfone, fluopyram, cyclobutrifluram, tioxazafen, imicyafos, and fluazaindolizine have at least one heterocyclic ring in their structures. In view of the importance of heterocyclic structure in the development of nematicides, this paper reviews the research progress of nematicidal active compounds of heterocyclic in recent years, and discusses the structure–activity relationship (SAR) and mechanism of action. It is hoped that it can provide new inspiration for the development of new nematicides.

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“…Fluoroalkenyl groups are a kind of active group that are capable of selection. Compounds obtained by combining fluoroalkenyl groups with thiazole, oxazole, or other heterocyclic structures can perform a high nematicidal activity [11,12]. Meanwhile, the fluoroalkenyl compounds also possess lower toxicity to vertebrates than organophosphate-or carbamate-based nematicides [12].…”

Section: Introductionmentioning

confidence: 99%

Fluoroalkenyl-Grafted Chitosan Oligosaccharide Derivative: An Exploration for Control Nematode Meloidogyne Incognita

Fan

Qin

Liu

et al. 2022

IJMS

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The exploration of novel, environmentally friendly, and efficient nematicides is essential, and modifying natural biomacromolecules is one feasible approach. In this study, 6-O-(trifluorobutenyl-oxadiazol)-chitosan oligosaccharide derivative was synthesized and characterized by FTIR, NMR, and TG/DTG. Its bioactivity and action mode against root-knot nematode M. incognita were estimated. The results show that the derivative shows high nematicidal activity against J2s, and egg hatching inhibitory activity at 1 mg/mL. The derivative may affect nematode ROS metabolism and further damage intestinal tissue to kill nematode. Meanwhile, by synergism with improving crop resistance, the derivative performed a high control effect on the nematode with low phytotoxicity. These findings suggested that chitosan oligosaccharide derivatives bearing fluoroalkenyl groups are promising green nematicides.

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Design, synthesis and nematicidal activitives of trifluorobutene amide derivatives against Meloidogyne incognita

Cited by 9 publications

References 21 publications

Bioisosterism and Scaffold Hopping in Modern Nematicide Research

Bioisosterism and Scaffold Hopping in Modern Nematicide Research

Recent research progress of heterocyclic nematicidal active compounds

Fluoroalkenyl-Grafted Chitosan Oligosaccharide Derivative: An Exploration for Control Nematode Meloidogyne Incognita

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