Antidotes for Reduction of Phytotoxicity of the Residues of Sulfonylurea Herbicides

Чкаников, Н. Д.; Spiridonov, Yu. Ya.; Халиков, С. С.; Muzafarov, A. M.

doi:10.32931/io1921r

Cited by 6 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…To eliminate such negative effects and to raise crop yields, herbicide safeners (also called herbicide antidotes or detoxifiers) are successfully used. Herbicide safeners [ 39 , 40 , 41 ] can be defined as agrochemicals that are able to neutralize phytotoxins in plants, thus protecting crop plants from herbicide injury. Safeners are harmless to crop plants (or even have a growth-stimulating effect), but do not affect the activity of herbicides against weeds.…”

Section: Resultsmentioning

confidence: 99%

Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

et al. 2023

View full text Add to dashboard Cite

The reaction between dithiomalondianilide (N,N’-diphenyldithiomalondiamide) and alkyl 3-aryl-2-cyanoacrylates in the presence of morpholine in the air atmosphere leads to the formation of alkyl 6-amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]- pyridine-5-carboxylates in 37–72% yields. The same compounds were prepared in 23–65% yields by ternary condensation of aromatic aldehydes, ethyl(methyl) cyanoacetate and dithiomalondianilide. The reaction mechanism is discussed. The structure of ethyl 6-amino-4-(4-methoxyphenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylate was confirmed by X-ray crystallography. Two of the prepared compounds showed a moderate growth-stimulating effect on sunflower seedlings. Three of the new compounds were recognized as strong herbicide safeners with respect to herbicide 2,4-D in the laboratory and field experiments on sunflower.

show abstract

Section: Resultsmentioning

confidence: 99%

Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

et al. 2023

View full text Add to dashboard Cite

show abstract

“…One of the most effective approaches to increase plant resistance towards herbicides is the activation of metabolic processes affected by herbicide safeners (also called herbicide antidotes or detoxifiers) [ 104 , 105 ]. Herbicide safeners can be defined [ 106 ] as agrochemicals suitable for neutralization of phytotoxins in plants, thus protecting crop plants from herbicide injury.…”

Section: Resultsmentioning

confidence: 99%

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

et al. 2023

View full text Add to dashboard Cite

The purpose of this work was to prepare new isatin- and monothiomalondiamide-based indole derivatives, as well as to study the properties of the new compounds. The four-component reaction of 5-R-isatins (R = H, CH3), malononitrile, monothiomalonamide (3-amino-3-thioxo- propanamide) and triethylamine in hot EtOH yields a mixture of isomeric triethylammonium 6′-amino-3′-(aminocarbonyl)-5′-cyano-2-oxo-1,2-dihydro-1′H- and 6′-amino-3′-(aminocarbonyl)- 5′-cyano-2-oxo-1,2-dihydro-3′H-spiro[indole-3,4′-pyridine]-2′-thiolates. The reactivity and structure of the products was studied. We found that oxidation of spiro[indole-3,4′-pyridine]-2′-thiolates with DMSO-HCl system produced only acidification products, diastereomeric 6′-amino-5′-cyano-5-methyl-2-oxo-2′-thioxo-1,2,2′,3′-tetrahydro-1′H-spiro-[indole-3,4′-pyridine]- 3′-carboxamides, instead of the expected isothiazolopyridines. The alkylation of the prepared spiro[indole-3,4′-pyridine]-2′-thiolates upon treatment with N-aryl α-chloroacetamides and α-bromoacetophenones proceeds in a regioselective way at the sulfur atom. In the case of α-bromoacetophenones, ring-chain tautomerism was observed for the S-alkylation products. According to NMR data, the compounds consist of a mixture of stereoisomers of 2′-amino-6′-[(2-aryl- 2-oxoethyl)thio]-3′-cyano-2-oxo-1′H-spiro[indoline-3,4′-pyridine]-5′-carboxamides and 5′-amino- 3′-aryl-6′-cyano-3′-hydroxy-2-oxo-2′,3′-dihydrospiro[indoline-3,7′-thiazolo[3,2-a]pyridine]-8′-carboxamides in various ratios. The structure of the synthesized compounds was confirmed by IR spectroscopy, HRMS, 1H and 13C DEPTQ NMR studies and the results of 2D NMR experiments (1H-13C HSQC, 1H-13C HMBC). Molecular docking studies were performed to investigate suitable binding modes of some new compounds with respect to the transcriptional regulator protein PqsR of Pseudomonas aeruginosa. The docking studies revealed that the compounds have affinity for the bacterial regulator protein PqsR of Pseudomonas aeruginosa with a binding energy in the range of −5.8 to −8.2 kcal/mol. In addition, one of the new compounds, 2′-amino-3′-cyano-5-methyl- 2-oxo-6′-{[2-oxo-2-(p-tolylamino)ethyl]thio}-1′H-spiro-[indoline-3,4′-pyridine]-5′-carboxamide, showed in vitro moderate antibacterial effect against Pseudomonas aeruginosa and good antioxidant properties in a test with 1,1-diphenyl-2-picrylhydrazyl radical. Finally, three of the new compounds were recognized as moderately active herbicide safeners with respect to herbicide 2,4-D in the laboratory experiments on sunflower seedlings.

show abstract

“…При крайне благоприятных токсикологических характеристиках сульфонилмочевин потенциальную опасность представляет их высочайшая фитотоксичность по отношению ко многим культурным растениям. Такие важнейшие сельскохозяйственные культуры как злаки (пшеница, рожь, ячмень, овёс) относительно устойчивы к сульфонилмочевинам, но возникает проблема с выращиванием культур, следующих в севообороте за злаками [18].…”

Section: механизмы действия и проблемы применения гербицидов из класс...unclassified

“…Подтверждением фитотоксического действия остатков сульфонилмочевин в почве является снижение в 2-9 раз урожаев льна, сахарной свёклы, чечевицы, гороха и картофеля, полученных через 1 год после обработки участка хлорсульфуроном в дозе 10-40 г/га. Остатки метсульфурон-метила в почве через год после применения в дозе 4,5 г/га снижали урожай люцерны на 38, картофеля -на 28% [18]. У культурных растений признаки повреждения сульфонилмочевинами проявляются угнетением корневой системы, недоразвитием корневых волосков, покраснением жилок, появлением хлороза, некроза и, в конечном итоге, наступлением полной гибели растений.…”

Section: механизмы действия и проблемы применения гербицидов из класс...unclassified

“…По мнению исследователей, количественные показатели потерь урожая различных культур зависят от персистентности суль-фонилмочевин в различных условиях [18]. Практикующие специалисты отмечают, что производные сульфонилмочевины существенно различаются по периоду полураспада в почве, длительность которого зависит от таких факторов, как кислотность почвы (чем ниже рН почвенного раствора, тем быстрее происходит деструкция), погодные условия -низкая температура и недостаток влаги тормозят процесс разложения, чем «короче» лето, тем меньше период активной микробиологической деструкции и тем больше вероятность проявления последействия в следующем вегетационном периоде [20,21].…”

Section: механизмы действия и проблемы применения гербицидов из класс...unclassified

See 1 more Smart Citation

Application of microbial biotechnologies to eliminate residues of herbicides of imidazolinone and sulfonylurea classes in soil (review)

Kolotova,

Nefedieva,

Gribust

et al. 2023

TaAE

View full text Add to dashboard Cite

The review is devoted to the problems of application of modern imidazolinone and ulfonylurea herbicides, as well as to the researches in the field of microbial iotechnology for remediation of contaminated soils. Data on the traits of the influence of residual amounts of herbicides from the classes of imidazolinones and sulfonylureas on target and subsequent crops in crop rotations are given in the article. The problems of monitoring of herbicide residues due to the variety of properties of components and decomposition mechanisms in the soil are shown. Ecological aspects of the influence of imidazolinones and sulfonylureas on soil microbiota and non-target organisms are considered. The results of studies of the biodegradation pathways of herbicide components, as well as conditions that contribute to the acceleration of destructive processes, are presented. The relevance of the search for microorganisms-destructors of imidazolinones and sulfonylureas for the production of biological products is substantiated. Microorganisms of different genera, such as Rhodococcus, Rahnella, Pseudomonas, Bacillus, Methylopila, Ancylobacter, Hansschlegelia, Klebsiella, and Arthrobacter, possess destructive potential against imidazolinones and sulfonylureas. The current data on the development of biological products to eliminate residues of imidazolinones and sulfonylureas in soils to reduce the phytotoxic effect are given.

show abstract

Antidotes for Reduction of Phytotoxicity of the Residues of Sulfonylurea Herbicides

Cited by 6 publications

References 0 publications

Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

Application of microbial biotechnologies to eliminate residues of herbicides of imidazolinone and sulfonylurea classes in soil (review)

Contact Info

Product

Resources

About