Design of novel CSA analogues as potential safeners and fungicides

Zheng, Yang; Liu, Bin; Gou, Zhaopin; Li, Yao; Zhang, Xiao; Wang, Yanqing; Shibata, Yu; Li, Yonghong; Sun, Dequn

doi:10.1016/j.bmcl.2014.12.085

Cited by 17 publications

(17 citation statements)

References 14 publications

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“…16 Directed synthesis studies have shown that subtle modifications to the structure of CSA can affect its bioactivity, identifying the retention of the cyclopropyl group as a chemical feature required for its safener activity. 17,18 Therefore, one explanation for CSA's species specificity is that this safener is metabolised to different derivatives that vary in their protective activity in different crops. To evaluate this hypothesis, we now report on the activity and associated metabolism of CSA in safener-responsive maize and nonresponsive wheat.…”

Section: Introductionmentioning

confidence: 99%

Safening activity and metabolism of the safener cyprosulfamide in maize and wheat

Giannakopoulos

Dittgen

Schulte

et al. 2020

Pest Management Science

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BACKGROUND Safeners extend the application of existing herbicides by selectively enhancing tolerance in large‐grained cereal crops. While their activity is linked to enhanced herbicide metabolism, their exact mode of action and reasons for their crop specificity have yet to be determined. In this study, we investigated the selectivity of the recently developed sulfonamide safener cyprosulfamide (CSA) in maize (Zea mays L.) and wheat (Triticum aestivum), focusing on its uptake, distribution and metabolism in the two species. RESULTS CSA protected maize, but not wheat, from injury by thiencarbazone‐methyl (TCM). This correlated with the selective enhanced detoxification of the herbicide in maize. CSA underwent more rapid metabolism in maize than in wheat, with the formation of a specific hydroxylated metabolite correlating with safening. Studies with the nsf1 mutant sweetcorn line showed that the hydroxylation of CSA was partly mediated by the cytochrome P450 CYP81A9. However, primary metabolites of CSA were chemically synthesised and tested for their ability to safen TCM in maize but when tested were inactive as safeners. CONCLUSION The results of this study suggest that the protection against TCM injury by CSA is linked to enhanced herbicide metabolism. This selective activity is due to the specific recognition of parent CSA in maize but not in wheat. Subsequent rapid oxidative metabolism of CSA led to its inactivation, demonstrating that cytochrome P450s regulate the activity of safeners as well as herbicides. © 2020 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

Safening activity and metabolism of the safener cyprosulfamide in maize and wheat

Giannakopoulos

Dittgen

Schulte

et al. 2020

Pest Management Science

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“…Therefore, commercially available pesticides can be used as intermediates or starting compounds, and lead compounds can be designed according to scientific methods [16,17,18]. In addition, structure–activity relationships, active substructure combinations, and bioisosterism have already been applied to design novel herbicide safener [19,20,21,22].…”

Section: Introductionmentioning

confidence: 99%

Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen

et al. 2019

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The herbicide fomesafen has the advantages of low toxicity and high selectivity, and the target of this compound is protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4). However, this herbicide has a long residual period and can have phytotoxic effects on succeeding crops. To protect maize from fomesafen, a series of thiazole phenoxypyridines were designed based on structure–activity relationships, active substructure combinations, and bioisosterism. Bioassays showed that thiazole phenoxypyridines could improve maize tolerance under fomesafen toxicity stress to varying degrees at a dose of 10 mg·kg−1. Compound 4i exhibited the best effects. After being treated by compound 4i, average recovery rates of growth index exceeded 72%, glutathione content markedly increased by 167% and glutathione S-transferase activity was almost 163% of fomesafen-treated group. More importantly, after being treated by compound 4i, the activity of PPO, the main target enzyme of fomesafen, recovered to 93% of the control level. The molecular docking result exhibited that the compound 4i could compete with fomesafen to bind with the herbicide target enzyme, which consequently attained the herbicide detoxification. The present work suggests that compound 4i could be developed as a potential safener to protect maize from fomesafen.

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“…On the other hand, active substructure combinations have also proved to be very significant for synthesizing novel safeners, and these combinations can provide useful information about chemical substituents. Novel acylsulfamoylbenzamide safeners with excellent bioactivity have been designed using the previously developed safener cyprosulfamide, as the leading compounds based on similar active substructures ( Scheme 1 ) [ 12 ]. Two compounds based on acylsulfamoylbenzamide have better bioactivities than cyprosulfamide and could serve as leading compounds in the design of new safeners.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates

Zhao

Zou

et al. 2018

Molecules

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A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from l-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR, 1H NMR, 13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl. Molecular docking modeling demonstrated that Compound 4e competed against chlorimuron-ethyl to combine with the herbicide target enzyme active site, causing the herbicide to be ineffective.

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Design of novel CSA analogues as potential safeners and fungicides

Cited by 17 publications

References 14 publications

Safening activity and metabolism of the safener cyprosulfamide in maize and wheat

Safening activity and metabolism of the safener cyprosulfamide in maize and wheat

Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen

Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates

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