Bifunctional quaternary ammonium salts based on benzo[1,2,3]thiadiazole-7-carboxylate as plant systemic acquired resistance inducers

Lewandowski, Piotr; Kukawka, Rafał; Pospieszny, H.; Śmiglak, Marcin

doi:10.1039/c3nj01613g

Cited by 32 publications

(43 citation statements)

References 14 publications

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“…12 It is also possible to synthesize HILs, which display two different biological functions. by inducing plant systemic acquired resistance towards viral diseases 18,19 or fungi. [13][14][15][16] HILs may be employed as a safer alternative to commonly available crop protection agents.…”

Section: Introductionmentioning

confidence: 99%

Herbicidal ionic liquids based on esterquats

et al. 2015

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Novel herbicidal ionic liquids (HILs) containing different anions and cations derived from ammonium esterquats were prepared by employing a simple, inexpensive pathway. The basic physicochemical properties of the synthesized salts (such as density, viscosity, refractive index, solubility and thermal stability) were determined.Additionally, their herbicidal efficacy was evaluated under greenhouse and field conditions with a subsequent assessment of biodegradability and toxicity (acute oral toxicity towards rats and rainbow trout, the growth inhibition test of green algae and the acute immobilization test using water flea). The results of greenhouse and field experiments revealed that the herbicidal activity of HILs comprising long alkyl chains has exceeded that of commercial plant protection products. The HIL containing the di(tallowoyloxyethyl)dimethylammonium cation exhibited notable biodegradability (63% after 28 days) and various toxicity classifications depending on the tested organism: category V towards rats with LC 50 4 2000 mg, category II towards fish with LC 50 /96 h at 10.62 mg L À1 , category I towards algae and daphnids with E r C 50 /72 h at 1.73 mg L À1 and EC 50 at 0.28 mg L À1 , respectively. These findings provide evidence that the synthesis of HILs with a specifically designed structure may be successfully employed for obtaining novel, efficient and environmentally friendly plant protection agents. † Electronic supplementary information (ESI) available: 1 H and 13 C NMR spectra, detailed testing procedures for: the acute toxicity test towards rats, the acute oral toxicity test towards rainbow trout, the growth inhibition test of green algae, the acute immobilization test using water flea. See

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Section: Introductionmentioning

confidence: 99%

Herbicidal ionic liquids based on esterquats

et al. 2015

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“…Six of the eight tested derivatives of isonicotinic acid indicate resistance inducing properties, which were expressed by decrease of necrotic area by 44 to 92 % in comparison to the control. Moreover, for three of examined 2,6-dichloroisonicotinate derivatives (N-butyl-N-methyl-2,6-dichloroisonicotinamide (3), N,N-bis(2-hydroxyethyl)-2,6-dichloroisonicotinamide (4) and N-Methyl-N-benzyl-2,6-dichloroisonicotinamide (5)), SAR induction properties were improved in comparison to 2,6-dichloroisonicotinic acid (1). Surprisingly, only in case of two of isonicotinic acid derivatives: N,N-dibutylisonicotinamide (7) and N-butyl-N-methylisonicotinamide (8) reduction of necrotic area by 44 % and 75 % was observed in comparison to control and isonicotinic acid (6), which did not show any SAR induction properties.…”

Section: Resultsmentioning

confidence: 99%

“…[2,3] One of them is systemic acquired resistance (SAR), which has a broad spectrum action against pathogens, most often simultaneously against bacteria, viruses and fungi. [4,5] Systemic acquired resistance, besides through pathogens attack, can also be induced by natural and synthetic substances (elicitors). The endogenous signaling molecule associated with SAR induction in plants is salicylic acid (SA).…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10] SAR inducers can be divided into two groups: natural (endogenous) like salicylic acid, oxalic acid, nicotinic acid and synthetic -2,6-dichloroisonicotinic acid, β-aminobutyric acid acibenzolar S-methyl ester (BTH) and their derivatives. [11][12][13][14][15][16][17][18] There are many advantage of using elicitors to induce the SAR phenomenon as a method of plant protection: (1) they do not directly interact with microorganisms which results in maintenance of the environmental equilibrium; [19] (2) elicitors activate plant resistance which has broad spectrum of actions against pathogens, most often simultaneously against fungi, viruses and bacteria; [4][5] (3) pathogens do not immunize against SAR inducers because those do not interact directly with the pathogens, furthermore, in contrast to typical plant protection products, pathogens do not immunize against systemic acquired resistance itself because this phenomenon is too complex; [20] (4) elicitors can be used in combination with another plant protection products to reduce their doze; [21] (5) method of application of SAR inducers is the same as typical plant protection techniques against pathogens. [8] In summary, high efficiency and broad spectrum of action against patho- gens makes application of SAR inducers to plant a very promising method of plant protection.…”

Section: Introductionmentioning

confidence: 99%

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Derivatives of Isonicotinic Acid as New Efficient Systemic Acquired Resistance (SAR) Inducers

2020

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Systemic acquired resistance (SAR) is one of the most promising ways to support plants in fight against viruses, bacteria and fungi. This phenomenon is activated by pathogen attack or artificially, by using resistance inducer (elicitor) which imitates the plant‐pathogen interaction. Both, biological or chemical factors interact with plants and stimulate their immune system against infections before first symptoms of diseases occurs. SAR inducing properties of elicitors could be potentially utilized to develop a new plant protection strategies. This paper presents synthesis, phytotoxicity and SAR induction efficacy of four newly obtained amide derivatives of 2,6‐dichloroisonicotinic acid and four known amide derivatives of isonicotinic acid. Induction of plant resistance tests were performed on tobacco Nicotiana tabacum var. Xanthi infected by Tobacco mosaic virus (TMV). Six of the eight presented substances indicate resistance inducing properties, which were expressed by decrease of necrotic area on leaves caused by viral infection by 44 to 92 % in comparison to the control plants. Moreover, obtained results show that presented compounds exhibited better plant resistance inducing properties than salicylic acid, oxalic acid and β‐aminobutyric acid used as reference.

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“…Novel types of dual functional salts include ILs which exhibit biological activity. Introduction of another functional counterion allows to obtain salts with additional properties (Lewandowski et al 2014). It is possible to synthesize HILs with a cation used as a plant growth regulator or fungicide and an anion manifesting high herbicidal activity (Pernak et al 2013(Pernak et al , 2014a.…”

Section: Introductionmentioning

confidence: 99%

Dicationic triazolium fungicidal ionic liquids with herbicidal properties

et al. 2019

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The purpose of the present study was to synthesize the dicationic ionic liquids exhibiting herbicidal and fungicidal activities. A homologue series of ten dicationic ionic liquids was synthesized using commercial triazole fungicide (tebuconazole) and evaluated in terms of their possible antifungal and herbicidal activities. Dicationic triazolium compounds containing different linkers were prepared via acid-base reaction between the corresponding dicationic hydroxides and herbicides in the form of free acids. Additionally, the ionic liquids were fully characterized using NMR and thermal analysis. The herbicidal efficacy was tested during greenhouse experiments, using lambsquarters and oilseed rape as the test plants. In the case of determination of antifungal activity, six fungal species were used: Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium culmorum, Fusarium oxysporum, Colletotrichum sp. and Monographella nivalis. The obtained results indicate that the conversion of compounds into dicationic ionic liquids affects their fungicidal and herbicidal activity. In the case of tests carried out on fungi, no difference in activity was observed at higher doses, except Monographella nivalis. However, at lower concentration (10 ppm), there is a reduction in efficacy compared to the reference substance. In addition, all obtained compounds are characterized by high activity.

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Bifunctional quaternary ammonium salts based on benzo[1,2,3]thiadiazole-7-carboxylate as plant systemic acquired resistance inducers

Cited by 32 publications

References 14 publications

Herbicidal ionic liquids based on esterquats

Herbicidal ionic liquids based on esterquats

Derivatives of Isonicotinic Acid as New Efficient Systemic Acquired Resistance (SAR) Inducers

Dicationic triazolium fungicidal ionic liquids with herbicidal properties

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