N6-α-haloacyl sydnone imine derivatives

Samarskaya, Alina S.; Cherepanov, I. A.; Godovikov, Ivan A.; Калинин, В. Н.

doi:10.1134/s0012500815080017

Cited by 4 publications

(8 citation statements)

References 4 publications

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“…It was found that all sydnone imine derivatives studied, except for one, showed a statistically significant effect on the seed germination and seedling development of corn. In contrast to N-3-aminosubstituted compounds 2 and 3 (Figure 2), which suppressed sunflower seed germination [32], the N-6-Boc-derivative 12 turned out to be ineffective on corn seeds. Furthermore, compound 13 not only failed to suppress plant development but, vice versa, showed a growth stimulating effect on seedlings and Experiments on the growth regulating activity of sydnone imine derivatives (4-14) were performed under thermostatic conditions using the corn (Zea mays L.) seeds of a Krasnodarskaya 12 cultivar [85].…”

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 82%

“…The hypothesis of using sydnone imines as plant growth regulators was suggested only quite recently and proposed in the recent work of Olshevskaya et al [32]. The authors aimed at finding chemical plant protection agents among new classes of chemical compounds with herbicidal, antidotal or growth regulatory activity.…”

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 99%

“…Figure 3. Effect of the sydnone imines 2 and 3 tested without and with the herbicide "Zinger" on sunflower seed germination for two concentrations [32].…”

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 99%

“…In 2018, Moiseev et al [85] investigated the growth-stimulating activity dependence on different structures of C4-un-Figure 3. Effect of the sydnone imines 2 and 3 tested without and with the herbicide "Zinger" on sunflower seed germination for two concentrations [32].…”

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 99%

“…Sydnone imines represent a class of mesoionic heterocyclic compounds [31] exhibiting a broad range of biological activities, and in this regard, they are successfully applied in medicine. Recently, sydnone imines were addressed as the plant phytoeffectors and reported to be potent growth modulators [32]. These compounds are prodrugs which after enzymatic activation and rearrangement can act as potent NO donors, and since NO is involved in the modulation of stress response, this class of compounds can be considered a source of prospective stress tolerance-enhancers as well.…”

Section: Introductionmentioning

confidence: 99%

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Sydnone Imines as a New Class of Promising Plant Growth and Stress Tolerance Modulators—A First Experimental Structure–Activity Overview

Cherevatskaya,

Cherepanov,

Kalganova

et al. 2024

Stresses

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Due to the oncoming climate changes, various environmental stresses (drought, salinity, heavy-metals, low or high temperatures, etc.) might dramatically affect crop yields and the quality of produced foods. Therefore, to meet the growing food demand of the human population, improvement of stress tolerance of the currently cultured crops is required. The knowledge of the molecular underlying mechanisms provides a versatile instrument to correct plant metabolism via chemical tools and to thereby increase their adaptive potential. This will preserve crop productivity and quality under abiotic stress conditions. Endogenously produced nitric oxide (NO) is one of the key signaling factors activating stress tolerance mechanisms in plants. Thus, the application of synthetic NO donors as stress-protective phytoeffectors might support maintaining plant growth and productivity under stressful conditions. Sydnone imines (sydnonimines) are a class of clinically established mesoionic heterocyclic NO donors which represent a promising candidate group for such phytoeffectors. Therefore, here, we provide an overview of the current progress in the application of sydnone imines as exogenous NO donors in plants, with a special emphasis on their potential as herbicides as well as herbicide antidotes, growth stimulants and stress protectors triggering plant tolerance mechanisms. We specifically address the structure–activity relationships in the context of the growth modulating activity of sydnone imines. Growth stimulating or antidote effects are typical for 4-α-hydroxybenzyl derivatives of sydnone imines containing an alkyl substituent in position N-3. The nature of the substituent of the N-6 atom has a significant influence on the activity profile and the intensity of the effect. Nevertheless, further investigations are necessary to establish reliable structure–activity relationships (SAR). Consequently, sydnone imines might be considered promising phytoeffector candidates, which are expected to exert either protective effects on plants growing under unfavorable conditions, or herbicidal ones, depending on the exact structure.

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Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 82%

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 99%

“…Figure 3. Effect of the sydnone imines 2 and 3 tested without and with the herbicide "Zinger" on sunflower seed germination for two concentrations [32].…”

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 99%

Section: Sydnone Imines As Phytoeffectors In Plantsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Sydnone Imines as a New Class of Promising Plant Growth and Stress Tolerance Modulators—A First Experimental Structure–Activity Overview

Cherevatskaya,

Cherepanov,

Kalganova

et al. 2024

Stresses

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Recent developments in the chemistry of sydnones and sydnone imines

Cherepanov

Moiseev

2020

Advances in Heterocyclic Chemistry

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Sydnone Imines: A Novel Class of Plant Growth Regulators

et al. 2023

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An increase in the yield of the main cereal crops in the context of global climate changes requires additional impacts on plants. Natural and synthetic plant growth regulators (PGRs) are used to increase plant productivity and reduce the injury level caused by abiotic stressors. There is a growing need for novel highly effective plant growth stimulants to exhibit their effects at low doses and to not pose an environmental threat or injury to the crop quality. The derivatives of sydnone imine (SI), a mesoionic heterocycle possessing a 1,2,3-oxadiazole core, have been used as medicines until now but have not been used for agricultural applications. Some SI derivatives have recently been found to exhibit PGR properties. Herein, we report on the study of the PGR potential of nine SI derivatives bearing variable substituents at N(3), C(4), and N6 positions of the heterocycle designed to disclose the “molecular structure-PGR activity” relationship in this family. The SI derivatives were used in a wide concentration range (10−9–10−4 mol/L) for a pre-sowing treatment of winter wheat (Triticum aestivum L., two cultivars) and maize (Zea mays L., two hybrids) seeds in germinating experiments. All compounds were found to affect the growth of the axial organs of germinants, with the growth-stimulating or -inhibitory effect as well as its rate being considerably different for wheat and maize and, in many cases, also for roots and shoots. In addition, a pronounced concentration dependence of the effect was disclosed for many cases. The features of the molecular structure of SIs affecting their growth-regulating properties were elucidated. Compounds 4, 6, 7, and 8, which had exhibited a growth-promoting effect in germinating experiments, were used at appropriate concentrations for pot experiments on the same crops. For all compounds, the experiments showed a stimulating effect on the growth of roots (up to 80%), shoots (up to 112%), leaf area (up to 113%), fresh weights of roots (up to 83%), and aerial parts of the plants (up to 87%) or only on some of these parameters. The obtained results show a healthy outlook for the use of SI derivatives as promoting agents for improving the growth of cereal crop plants.

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N6-α-haloacyl sydnone imine derivatives

Cited by 4 publications

References 4 publications

Sydnone Imines as a New Class of Promising Plant Growth and Stress Tolerance Modulators—A First Experimental Structure–Activity Overview

Sydnone Imines as a New Class of Promising Plant Growth and Stress Tolerance Modulators—A First Experimental Structure–Activity Overview

Recent developments in the chemistry of sydnones and sydnone imines

Sydnone Imines: A Novel Class of Plant Growth Regulators

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