Substituted α‐(phenylhydrazono)phenylacetonitrile derivatives. Part 2: synthesis and biological activity of pro‐pesticides

Flury, Thomas; Hall, Roger G.; Karrer, Friedrich; Kienast, Heinz; Leuenberger, Katrin; Pascual, Alfons; Rindlisbacher, Alfred; Trah, Stephan; Widmer, Hans-Joerg

doi:10.1002/ps.1166

Cited by 5 publications

(5 citation statements)

References 4 publications

(6 reference statements)

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“…This material could be cleaved inside the plant or pest organism by spontaneous chemical conversion or enzyme-catalyzed metabolism. The enzyme unique to the plant crucially determines the proper approach to the preparation of pro-drugs. , Related works have achieved this enzyme through engineering mechanisms to release the active molecule within the plants. For instance, a sulfonylurea pro-herbicide can be activated in transgenic tobacco using the TA29 promoter to express a bacterial P450 gene in a tissue-specific manner .…”

Section: Resultsmentioning

confidence: 99%

β-Glucosidase Involvement in the Bioactivation of Glycosyl Conjugates in Plants: Synthesis and Metabolism of Four Glycosidic Bond Conjugates in Vitro and in Vivo

Xia

Wen

Wang

et al. 2014

J. Agric. Food Chem.

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Mobile glucose-pesticide conjugates in the phloem are often restricted by decreases in biological activity. However, plants can bioactivate endogenous glucosides, which are assumed as able to bioactivate exogenous conjugates. In this study, four glycosidic bonds (O-, S-, N-, and C-glycosidic bonds) of glucose-pesticide conjugates were designed and synthesized, and then metabolism assays were carried out in vitro and in vivo. Results showed that β-glucosidases played a role in the hydrolysis of O-glycosidic bond conjugates in Ricinus communis L. The liberated aglycons possessed insecticidal activities against Plutella xylostella L. and Spodoptera litura F. These results could help establish methods of circumventing the mutual exclusivity of phloem mobility and biological activity by hydrolyzing endogenous β-glucosidases.

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Section: Resultsmentioning

confidence: 99%

β-Glucosidase Involvement in the Bioactivation of Glycosyl Conjugates in Plants: Synthesis and Metabolism of Four Glycosidic Bond Conjugates in Vitro and in Vivo

Xia

Wen

Wang

et al. 2014

J. Agric. Food Chem.

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“…Biological results against insect pests are depicted as the concentration in mg a.i. l −1 at which 80% or more mortality of larvae was observed, using methods described in the literature …”

Section: Molecular Matched Pair Analysismentioning

confidence: 99%

“…l −1 at which 80% or more mortality of larvae was observed, using methods described in the literature. 40 The trifluoromethyl pyridine compound 11 is clearly more potent than the phenyl analogue 12; at a concentration of 12.5 mg a.i. l −1 , 100% of Spodoptera littoralis and Diabrotica baltealta larvae were killed, whereas with the phenyl analogue 12, no insecticidal activity was observed at a concentration of 100 mg a.i.…”

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confidence: 99%

The importance of trifluoromethyl pyridines in crop protection

Burriss

Edmunds

Emery

et al. 2018

Pest Management Science

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The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporated into molecules with useful biological properties. During the period 1990 to September 2017, 14 crop protection products bearing a trifluoromethyl pyridine have been commercialized or proposed for an ISO common name, covering fungicides, herbicides, insecticides and nematicides. Chemical processes have been developed to provide trifluoromethyl pyridine intermediates, from non-fluorinated pyridine starting materials, at scale and with affordable costs of goods. These attractive starting materials were readily adopted by research chemists, and elaborated through simple chemical modifications into new active ingredients. In a second approach, substituted trifluoromethyl pyridine rings have been constructed from acyclic, trifluoromethyl starting materials, which again has served to identify new active ingredients. Molecular matched pair analysis reveals subtle, yet important differences in physicochemical and agronomic properties of trifluoromethyl pyridines compared with the phenyl analogues. This review focuses on the past 27 years, seeking to identify reasons behind the success of such research programmes, and inspire the search for new crop protection chemicals containing the trifluoromethyl pyridine ring. © 2017 Society of Chemical Industry.

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“…[31] Furthermore, derivatives have been used as acaricides and insecticides due to their tendency to inhibit oxidative phosphorylation. [32]…”

Section: Introductionmentioning

confidence: 99%

Light‐Induced Metal‐Free Generation of Cyanocarbenes from Alkynyl Triazenes for the Synthesis of Nitrile Derivatives

Michel,

Grieser,

Mackenroth

et al. 2023

Angew Chem Int Ed

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The chemistry of alkynyl triazenes is an emerging field for organic chemists and especially acid‐induced nucleophilic functionalizations, either directly, or after a prior reaction towards aromatic triazenes under extrusion of nitrogen, paved the way for fruitful strategies. In contrast, the chemical behavior of alkynyl triazenes upon irradiation with light is still unknown. Herein we present the first photoactivation of alkynyl triazenes that triggers an uncommon reactivity pattern involving the cleavage of the N1‐N2 bond of the triazene moiety resulting in a unique approach to cyanocarbenes from a readily available, stable, and insensitive precursor. This allows to access various nitrile compounds without the use of a toxic cyanating agent by exploiting the reactivity pattern of carbenes. By variation of the reaction conditions and light sources, different substitution patterns can be obtained selectively in good yields under mild and metal‐free conditions, thus introducing the alkynyl triazene unit as a photo accessible methylene nitrile synthon. Using this synthon, subclasses like α‐alkoxynitriles, α‐aminonitriles and α‐cyanohydrazones become easily available. These exhibit synthetically valuable substitution patterns for the synthesis of pharmaceuticals, intermediates for total synthesis and amino acid synthesis.

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Substituted α‐(phenylhydrazono)phenylacetonitrile derivatives. Part 2: synthesis and biological activity of pro‐pesticides

Cited by 5 publications

References 4 publications

β-Glucosidase Involvement in the Bioactivation of Glycosyl Conjugates in Plants: Synthesis and Metabolism of Four Glycosidic Bond Conjugates in Vitro and in Vivo

β-Glucosidase Involvement in the Bioactivation of Glycosyl Conjugates in Plants: Synthesis and Metabolism of Four Glycosidic Bond Conjugates in Vitro and in Vivo

The importance of trifluoromethyl pyridines in crop protection

Light‐Induced Metal‐Free Generation of Cyanocarbenes from Alkynyl Triazenes for the Synthesis of Nitrile Derivatives

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