The chemistry, herbicidal and fungicidal activities of 2,1,3‐benzothiadiazoles

Daalen, J. J. Van; Daams, J.; Koopman, H.; Tempel, A.

doi:10.1002/recl.19670861102

Cited by 21 publications

(12 citation statements)

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“…In conclusion, we proposed an efficient method for the synthesis of fused [1,2,5]thiadiazoles by the reaction of orthodiaminopyridines and benzenes with S 2 Cl 2 . This method allows one to obtain target bicyclic molecules even in those cases where conventional procedures applying thionyl chloride do not work, for example [1,2,5]thiadiazolo [3,4-b]pyridines with electron-withdrawing substituents. The most π-deficient compounds react with neutral carbon nucleophiles under mild conditions to give the corresponding 1,4-adducts to the pyridine ring.…”

Section: Discussionmentioning

confidence: 99%

“…[2] [1,2,5]Thiadiazolo [4,3-b]pyridines have been considered as mammalian JAK kinase inhibitors [3] and potent Somatostatin sst 1 receptor antagonists. [4] Benzo/pyrido [1,2,5]thiadiazole skeleton was incorporated into funnel-shaped molecules studied as peripheral acceptors for organic photovoltaic applications [5] as well as small semi-conducting organic molecules. [6,7] The majority of known [1,2,5]thiadiazolo [4,3-b]pyridines were synthesized from 2,3-diaminopyridines and thionyl chloride via thiadiazole ring closure.…”

Section: Introductionmentioning

confidence: 99%

“…[4] The above mentioned synthetic procedures afforded [1,2,5]thiadiazolo [4,3-b]pyridines mainly with electron-donating substituents in pyridine ring. Recently we were involved in the study of highly electrophilic azolo[b]pyridines and faced an unexpected problem during the synthesis of [1,2,5]thiadiazolo [4,3-b]pyridines bearing electron-withdrawing groups. It turned out that classical methods did not work and we were unable to obtain target [1,2,5]thiadiazolo [4,3b]pyridines in acceptable yields.…”

Section: Introductionmentioning

confidence: 99%

“…

General method for the annulation of [1,2,5]thiadiazole ring to pyridine and benzene cycle has been developed using sulfur monochloride as a sulfur source. On this basis a number of [1,2,5]thiadiazolo[4,3-b]pyridines and benzo[c]thiadiazoles were synthesized. The most π-deficient [1,2,5]thiadiazolo[4,3b]pyridines readily react with neutral carbon nucleophiles such as CH-acids, indoles, pyrrole and phloroglucinol to give 1,4adducts.

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confidence: 99%

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A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C‐Nucleophiles

Fedorenko,

Ivanova,

Minyaev

et al. 2023

ChemistrySelect

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General method for the annulation of [1,2,5]thiadiazole ring to pyridine and benzene cycle has been developed using sulfur monochloride as a sulfur source. On this basis a number of [1,2,5]thiadiazolo[4,3‐b]pyridines and benzo[c]thiadiazoles were synthesized. The most π‐deficient [1,2,5]thiadiazolo[4,3‐b]pyridines readily react with neutral carbon nucleophiles such as CH‐acids, indoles, pyrrole and phloroglucinol to give 1,4‐adducts.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…

…”

mentioning

confidence: 99%

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A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C‐Nucleophiles

Fedorenko,

Ivanova,

Minyaev

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

General method for the annulation of [1,2,5]thiadiazole ring to pyridine and benzene cycle has been developed using sulfur monochloride as a sulfur source. On this basis a number of [1,2,5]thiadiazolo[4,3‐b]pyridines and benzo[c]thiadiazoles were synthesized. The most π‐deficient [1,2,5]thiadiazolo[4,3‐b]pyridines readily react with neutral carbon nucleophiles such as CH‐acids, indoles, pyrrole and phloroglucinol to give 1,4‐adducts.

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“…The antifungal activityofbenzo-1-thiadiazoles, which has been detected at various test sites, is well known. [1][2][3]. However, there is no a unified method for the primary testing of antifungal drugs.…”

Section: Introductionmentioning

confidence: 99%

Statistical modeling of antifungal activity of substituted benzo-1-thia- and selenium diazoles

K¹

2020

World J. Bio. Pharm. Health Sci.

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Statistical methods revealed a close relationship between antifungal activity (suppression of the growth of the mycelium of the fungi of the species Venturia inaqualis, Aspergillus niger and Fusarium moniliforme) and the molecular structure of the substituted benzo-1-thiadiazoles and benzo-1-seleniumdiazoles. The molecular pseudopotential is used as the explanatory variable in the regression equations. It was established the threshold dependence of the antifungal activity on the pseudopotential of the molecule. The explanatory variable exceeding of its threshold value leads to a rapid linear increase in bioactivity for all species of fungi. Antifungal activity of drugs is low to the threshold value of the molecular pseudopotential and does not have a significant relationship with the variability of the molecular structure of the chemical compounds.

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Influence of chlorine substituents on biological activity of chemicals: a review

Naumann

2000

Pest. Manag. Sci.

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A number of well known polychlorinated chemicals are toxicologically and environmentally unsafe. Because of their persistence they are in the focus of public discussions against chlorine chemistry. However, chlorinated organic chemicals in the molecular weight range between 200 and 600 constitute an important and indispensable segment in the arsenal of existing biologically active chemicals used as pharmaceuticals or crop‐protection agents. Over the course of time it has been found empirically that the introduction of a chlorine atom into one or more specific positions of a biologically active molecule may substantially improve the intrinsic biological activity. In some cases the presence of a chlorine atom is crucial for significant activity in compounds derived both from nature and chemical synthesis. But in other cases chlorination diminishes or abolishes biological activity, as shown for chlordane homologues. Thus a chlorine atom, like any other substituent, is a modulator of activity. Almost all non‐reactive chlorinated chemicals and chlorine‐free chemicals are devoid of any biological activity at the highest concentration typically used in primary screening tests for discovery of useful biological properties. The influence of a substituent such as chlorine on the biological activity of a potential drug or crop protection agent still has to be established empirically in biological experiments designed to detect desired activity or toxicological properties. Sometimes chlorine does prove to be the optimum for improvement of activity. Long‐term rigorous investigations of several hundred chlorinated compounds, registered by the authorities as pharmaceutical drugs or crop‐protection agents, show that the generalisation ‘all chlorinated chemicals are dangerous’, deduced from the negative toxicological properties of a hundred chlorinated and reactive compounds of low molecular weight that are relevant in terms of safe working conditions in the chemical industry and for ecological safety, is not justified. Chlorinated compounds are not necessarily toxic or dangerous. Highly reactive chemicals or polychlorinated compounds cannot be compared with regard to toxicological properties with unreactive compounds having a low degree of chlorination. The chlorine atom, as one of many possible substituents used in synthetic organic chemistry, will remain in the future one of the important tools for probing structure–activity relationships in life science research and as a molecular component in commercialised compounds, in order to provide safer, more selective and more environmentally compatible products with higher activity for medicine and agriculture. © 1999 WILEY‐VCH Verlag GmbH

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The chemistry, herbicidal and fungicidal activities of 2,1,3‐benzothiadiazoles

Abstract: The synthesis and test results on the herbicidal and fungicidal activities of a large number of 2,1,3‐benzothiadiazoles, mainly 4,5,7‐trisubstituted derivatives, are described and discussed.

Cited by 21 publications

References 1 publication

A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C‐Nucleophiles

A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C‐Nucleophiles

Statistical modeling of antifungal activity of substituted benzo-1-thia- and selenium diazoles

Influence of chlorine substituents on biological activity of chemicals: a review

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