Evidence map›Paper›PMID 41465303›Full record

ArticleInternational journal of molecular sciences2025

Synthesis, Reactions, and Agrochemical Studies of New 4,6-Diaryl-2-hydrazinylnicotinonitriles.

Victor V Dotsenko, Vladislav K Kindop, Vyacheslav K Kindop, Renat G Achmiz, Arina G Levchenko, Polina G Dakhno, Azamat Z Temerdashev, Yu-Qi Feng, Quan-Fei Zhu, Eva S Daus and 5 more

Abstract read
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In one paragraph

Article in International journal of molecular sciences, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

  1. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

15 authors.

Victor V DotsenkoDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0000-0001-7163-0497
Vladislav K KindopDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0009-0002-9960-9440
Vyacheslav K KindopDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0000-0002-9005-9668
Renat G AchmizDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.
Arina G LevchenkoDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0000-0003-4787-7072
Polina G DakhnoDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0000-0002-5581-0241
Azamat Z TemerdashevDepartment of Analytical Chemistry, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0000-0002-8048-4740
Yu-Qi FengSchool of Bioengineering and Health, Wuhan Textile University, 1 Sunshine Avenue, Jiang Xia District, Wuhan 430200, China.ORCID 0000-0003-1107-5385
Quan-Fei ZhuSchool of Bioengineering and Health, Wuhan Textile University, 1 Sunshine Avenue, Jiang Xia District, Wuhan 430200, China.ORCID 0000-0003-1539-0227
Eva S DausDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.ORCID 0009-0007-8244-5925
Igor V YudaevFaculty of Energetics, Kuban State Agrarian University, 13 Kalinina St., 350044 Krasnodar, Russia.ORCID 0000-0002-3435-4873
Yuliia V DausFaculty of Energetics, Kuban State Agrarian University, 13 Kalinina St., 350044 Krasnodar, Russia.ORCID 0000-0001-9120-7637
Alexander V AksenovDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia.ORCID 0000-0002-6644-9949
Nicolai A AksenovDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia.ORCID 0000-0002-7125-9066
Inna V AksenovaDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia.ORCID 0000-0002-8083-1407

Funding

National Natural Science Foundation of China 22361132526Russian Science Foundation 24-43-00003
6 · The paper itself

Abstract

This work aimed to synthesize new derivatives of 2-hydrazinylpyridine-3-carbonitrile and to investigate their biological activity as safeners for the 2,4-D herbicide. The new 2-hydrazinylnicotinonitriles were obtained in high yields (up to quantitative) under mild conditions (25 °C, dioxane) by treating 4,6-diaryl-2-bromo-3-cyanopyridines with hydrazine hydrate. The latter were synthesized by brominating 2-(3-oxo-1,3-diarylpropyl)malononitriles, the Michael adducts, which are readily available from 1,3-diarylpropenones (chalcones) and malononitrile. An unusual side product of the bromination/carbocyclization was isolated and characterized; it consisted of co-crystals of 3-benzoyl-4-hydroxy-4-phenyl-2,6-di-(p-tolyl)cyclohexane-1,1-dicarbonitrile and 3-benzoyl-5-bromo-4-hydroxy-4-phenyl-2,6-di-(p-tolyl)cyclohexane-1,1-dicarbonitrile at a ~4:6 ratio. The new 2-hydrazinylnicotinonitriles react with halogen-containing aromatic aldehydes to form the corresponding hydrazones. The biological activity of the new nicotinonitriles was examined for their function as 2,4-D antidotes. It was found that, under laboratory conditions, eight of the synthesized compounds exhibited a notable antidote effect against 2,4-D on sunflower seedlings.

Indexed as

AgrochemicalsHerbicidesHydrazinesNitrilesMolecular StructureAgrochemicalsHerbicidesHydrazinesNitriles2,4-D herbicide safeners2-bromo-3-cyanopyridines2-hydrazinylpyridinesbrominationhydrazonesmalononitrileMichael adductsunsaturated ketones

Identifiers

PMID41465303
PMCPMC12733256

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.