scholarly journals Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4396
Author(s):  
Witold Stachowiak ◽  
Radosław Szumski ◽  
Jan Homa ◽  
Marta Woźniak-Karczewska ◽  
Anna Parus ◽  
...  

Efficient use of herbicides for plant protection requires the application of auxiliary substances such as surfactants, stabilizers, wetting or anti-foaming agents, and absorption enhancers, which can be more problematic for environment than the herbicides themselves. We hypothesized that the combination of sulfonylurea (iodosulfuron-methyl) anion with inexpensive, commercially available quaternary tetraalkylammonium cations could lead to biologically active ionic liquids (ILs) that could become a convenient and environment-friendly alternative to adjuvants. A simple one-step synthesis allowed for synthesizing iodosulfuron-methyl based ILs with high yields ranging from 88 to 96% as confirmed by UV, FTIR, and NMR. The obtained ILs were found to possess several favorable properties compared to the currently used sodium salt iodosulfuron-methyl, such as adjustable hydrophobicity (octanol-water partition coefficient) and enhanced stability in aqueous solutions, which was supported by molecular calculations showing cation–anion interaction energies. In addition, soil mobility and volatility of ILs were more beneficial compared to the parental herbicide. Herbicidal activity tests toward oil-seed rape and cornflower revealed that ILs comprising at least one alkyl chain in the decyl to octadecyl range had similar or better efficacy compared to the commercial preparation without addition of any adjuvant. Furthermore, results of antimicrobial activity indicated that they were practically harmless or slightly toxic toward model soil microorganisms such as Pseudomonas putida and Bacillus cereus.

2020 ◽  
Vol 18 (1) ◽  
pp. 1282-1293
Author(s):  
Marcin Praczyk ◽  
Katarzyna Wielgusz ◽  
Witold Stachowiak ◽  
Michał Niemczak ◽  
Juliusz Pernak

AbstractIn the framework of this research, four new herbicidal ionic liquids (HILs) comprising chlorsulfuron as the anion were synthesized and characterized. The new salts with chlorsulfuron contained the following cations: tetramethylammonium, didecyldimethylammonium, benzyltrimethylammonium and cholinium. All products were obtained with high yields exceeding 90% via acid–base reaction or ion exchange reaction, by the use of environment-friendly solvents. The structures of all synthesized HILs were confirmed by FT-IR, 1H NMR and 13C NMR analyses. Their efficacy against weeds has been studied under field conditions in fiber flax. All HILs showed herbicidal activity but efficiency was highly dependent on the type of cation and weed species. There were no statistically significant differences in the effectiveness of HILs toward common lambsquarters compared to the reference herbicide, except for salt with cholinium cation that showed significantly lower efficiency. As regards barnyard grass control, all HILs exhibited significantly lower efficacy than that of the reference herbicide, except for didecyldimethylammonium salt that showed similar activity. The synthesized products did not cause damage to flax plants. The obtained results confirmed that the herbicidal effectiveness of the active ingredient (chlorsulfuron) in the form of an ionic liquid can be adjusted by the selection of an appropriate cation in the synthesis.


2019 ◽  
Vol 23 (8) ◽  
pp. 860-900 ◽  
Author(s):  
Chander P. Kaushik ◽  
Jyoti Sangwan ◽  
Raj Luxmi ◽  
Krishan Kumar ◽  
Ashima Pahwa

N-Heterocyclic compounds like 1,2,3-triazoles serve as a key scaffolds among organic compounds having diverse applications in the field of drug discovery, bioconjugation, material science, liquid crystals, pharmaceutical chemistry and solid phase organic synthesis. Various drugs containing 1,2,3-triazole ring which are commonly available in market includes Rufinamide, Cefatrizine, Tazobactam etc., Stability to acidic/basic hydrolysis along with significant dipole moment support triazole moiety for appreciable participation in hydrogen bonding and dipole-dipole interactions with biological targets. Huisgen 1,3-dipolar azide-alkyne cycloaddition culminate into a mixture of 1,4 and 1,5- disubstituted 1,2,3-triazoles. In 2001, Sharpless and Meldal came across with a copper(I) catalyzed regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles by cycloaddition between azides and terminal alkynes. This azide-alkyne cycloaddition has been labelled as a one of the important key click reaction. Click synthesis describes chemical reactions that are simple to perform, gives high selectivity, wide in scope, fast reaction rate and high yields. Click reactions are not single specific reaction, but serve as a pathway for construction of simple to complex molecules from a variety of starting materials. In the last few decades, 1,2,3-triazoles attracted attention of researchers all over the world because of their broad spectrum of biological activities. Keeping in view the biological importance of 1,2,3-triazole, in this review we focus on the various synthetic routes for the syntheisis of 1,4-disubstituted 1,2,3-triazoles. This review involves various synthetic protocols which involves copper and non-copper catalysts, different solvents as well as substrates. It will boost synthetic chemists to explore new pathway for the development of newer biologically active 1,2,3-triazoles.


2019 ◽  
Vol 16 (7) ◽  
pp. 953-967 ◽  
Author(s):  
Ghodsi M. Ziarani ◽  
Fatemeh Mohajer ◽  
Razieh Moradi ◽  
Parisa Mofatehnia

Background: As a matter of fact, nitrogen as a hetero atom among other atoms has had an important role in active biological compounds. Since heterocyclic molecules with nitrogen are highly demanded due to biological properties, 4-phenylurazole as a compound containing nitrogen might be important in the multicomponent reaction used in agrochemicals, and pharmaceuticals. Considering the case of fused derivatives “pyrazolourazoles” which are highly applicable because of their application for analgesic, antibacterial, anti-inflammatory and antidiabetic activities as HSP-72 induction inhibitors (I and III) and novel microtubule assembly inhibitors. It should be mentioned that spiro-pyrazole also has biological activities like cytotoxic, antimicrobial, anticonvulsant, antifungal, anticancer, anti-inflammatory, and cardiotonic activities. Objective: Urazole has been used in many heterocyclic compounds which are valuable in organic syntheses. This review disclosed the advances in the use of urazole as the starting material in the synthesis of various biologically active molecules from 2006 to 2019. Conclusion: Compounds of urazole (1,2,4-triazolidine-3,5-dione) are the most important molecules which are highly active from the biological perspective in the pharmaceuticals as well as polymers. In summary, many protocols for preparations of the urazole derivatives from various substrates in multi-component reactions have been reported from different aromatic and aliphatic groups which have had carbonyl groups in their structures. It is noted that several catalysts have been synthesized to afford applicable molecules with urazole scaffolds. In some papers, being environmentally friendly, short time reactions and high yields are highlighted in the protocols. There is a room to synthesize new catalysts and perform new reactions by manipulating urazole to produce biologically active compounds, even producing chiral urazole component as many groups of chiral urazole compounds are important from biological perspective.


Solids ◽  
2021 ◽  
Vol 2 (1) ◽  
pp. 60-75
Author(s):  
Salavat S. Khalikov

Because of the rapid development of nanotechnologies, materials, in particular, solid dispersions (SDs), which are actively introduced into the life of modern man, have been obtained. Special progress in this area is observed in industry and medicine. The use of SDs in agriculture is lagging far behind, despite the growing number of scientific papers on this topic. At the same time, the prospects for the introduction of SDs in the agro-industrial complex are obvious. The review presents the results of research on the development of innovative preparations based on SD to protect plants from diseases and pests of cultivated plants, as well as parasiticides to protect animal health based on modern achievements of nanotechnology. One of these technologies is the methods of mechanochemistry, which improve the properties of poorly soluble biologically active substances by their joint mechanical treatment with water-soluble polymers and auxiliary substances.


2021 ◽  
pp. 15-23
Author(s):  
V. F. Pivovarov ◽  
A. V. Soldatenko ◽  
O. N. Pyshnaya ◽  
L. K. Gurkina

The article reflects the issues of the current state of scientific research at the FSBSI FSVC, shows the directions and prospects for the development of selection and seed production of vegetable crops. The main mission of the selection and seed-growing work of the FSVC is the creation and reproduction of varieties and hybrids of vegetable and melon crops of a new generation, characterized by resistance to abiotic and biotic stressors, high productivity and product quality. One of the main ways to increase the efficiency of the breeding process is the use of modern methods of biotechnology and molecular genetics, which make it possible to obtain new genotypes and reduce the time of breeding. Success has been achieved in the creation of homozygous lines of cabbage, squash, cucumber, carrots. For the first time, it was possible to complete a full cycle of obtaining doubled radish haploids in microspore culture in vitro. The institution pays special attention to immunological research on the resistance of crops and new varieties to diseases, as well as protecting plants from pests and diseases. Phytosanitary monitoring, assessment and selection of resistant genotypes are carried every years. One of the important theoretical and practical problems solved at the institution is the development of environmentally friendly products based on preparations obtained from plants with a high content of biologically active compounds with adaptogenic properties. In the center, a new direction of research in traditional breeding has received significant development - the creation of varieties of vegetable plants with an increased content of biologically active substances and antioxidants, on the basis of which functional products are created. The persistence of modern varieties and hybrids of table carrots, depending on the biochemical composition, has been studied. Methods for enriching vegetable plants with micronutrients are being developed. A large amount of scientific research is being carried out on the development of technologies for the cultivation of new varieties and hybrids, as well as technologies for their seed production. At the branches located in different soil and climatic conditions, hospitals were established to study the interaction of factors controlling soil fertility and the productivity of vegetable crops in agrocenoses (crop rotation, soil treatment systems, fertilizers and plant protection). In general, at the FSBSI FSVC, all research is aimed at developing and improving methods in breeding and seed production of vegetable crops, creating new breeding achievements and developing varietal technologies for their cultivation.


2021 ◽  
pp. 58-64
Author(s):  
I. S. Mastyaev ◽  
A. F. Agafonov ◽  
L. V. Krivenkov

Relevance. The success of breeding work is largely determined by the source material, the search and creation of which for target breeding begins with the collection and study of collectible samples for the alignment of morphological features; for the precocity and amity of maturation; for the keeping quality and transportability of bulbs; for the quality of vegetable products (high content of biologically active substances and antioxidants); for resistance to biotic and abiotic stressors of a specific growing zone.Materials and methods. On the basis of the North Caucasus branch FSBSI FSVC, 90 samples of spring onions from 26 countries of the world were evaluated in the number nursery for the period from 2017 to 2019, 71 of them were varieties and 19 were F1 hybrids. In a hybrid nursery, 25 hybrid combinations obtained from FSBSI FSVC (VNIISSOK) were evaluated. The laying and placement of experiments, agricultural techniques of cultivation, accounting and evaluation of economically valuable traits, biochemical analyses were carried out according to generally accepted methods. The standards are the new Primo and Ampex varieties of the selection of the FSBSI FSVC and the Italian F1 hybrid Ranko, which were placed every 10 collection samples.Results.According to the results of the assessment, among the studied F1 varieties and hybrids, sources of economically valuable traits such as yield (20-27 t/ha), precocity (80-90 days), preservation (more than 85%) when laid for long-term storage up to 7 months, purple, white and pink color of bulbs, as well as sources of long-shaped bulbs were identified. The greatest interest for breeding for yield is represented by 9 promising varieties and 9 F1 hybrids of onions of various origins, as well as 4 hybrid combinations that were distinguished by high yields, the yield of marketable products and the mass of marketable bulbs. These samples are recommended for use in the breeding process as sources for the creation of new varieties and hybrids with high yields for the agro-climatic conditions of the foothill zone of the North Caucasus.r breeding


2021 ◽  
Vol 447 (3) ◽  
pp. 70-75
Author(s):  
P.N. Naguman ◽  
A.A. Zhorabek ◽  
A.S. Amanzholova ◽  
I.V. Kulakov ◽  
A.N. Rakhimbaeva

Everyone knows that forest air is very good for health, and one of the most important reasons for this is the presence of phytoncides in it, which kill or suppress pathogens and have a healing effect. Also, phytoncides are one of the factors of the natural immunity of plants (plants sterilize themselves with the products of their vital activity). Their large number is allocated by plants. One of them is the common bird cherry. Cherry-a representative of the genus of plums of the Rosaceae family. The view includes low trees and shrubs. Cheremukha-forest orderly. Its flowers and leaves are rich in phytoncides, thanks to which they exude an alluring aroma. However, when they break down, they release prussic acid, which is dangerous for all living things. This gave them the opportunity to attract and destroy pests. Phytoncides are volatile biologically active substances formed by plants that kill or inhibit the growth and development of bacteria, microscopic fungi, and protozoa. In addition to all of the above, bird cherry has exceptional properties. The strong, somewhat intoxicating scent of flowers and leaves cleanses the air of germs. Antimicrobial properties of phytoncides have led to a large number of studies on their use in medicine, veterinary medicine, plant protection, storage of fruit and vegetable products, in the food industry and other areas of practice. Almost all parts of the plant have bactericidal, fungicidal and insecticidal properties. In folk medicine, bird cherry has long been used as an astringent, fixing, anti-inflammatory and anti-scurvy agent. Bird cherry produces the most powerful phytoncides containing prussic acid. Protozoa die under the influence of bird cherry phytoncides in 5 minutes. On the basis of numerous studies, the time of death of protozoa after noncontact exposure to phytoncidal plants has been established. Especially a lot of phytoncides are released by young leaves in spring and summer, in autumn phytoncides are released much less. The presence of tannins and essential oil in the fruit has an anti-inflammatory effect, which is used to treat inflammatory processes in the gastrointestinal tract and dysentery. The infusion of cherry fruits has a destructive effect on microorganisms. Preparations of the fruits of the common cherry have an antiseptic effect. They are used in dental practice in the treatment of inflammatory processes of the oral mucosa, paradontosis, toothache and hypovitaminosis.


Author(s):  
M. SBANCA ◽  
C. JIANU ◽  
I. JIANU

.Colloidal features [foaming capacity (FC); foam stability (FS) and foam density (FD)] of conditioning auxiliaries (additives) of plant protection active principles constitute, together with toxicity, a decisive technical index in forming administering receipts in modern ecological agriculture and foodstuff processing all during the agroalimentary processing and consumption chain. In this paper we show the results of a study on a new class of superficial active compounds salefied polyether ( = 3 – 20) primary amides. As diderived glymes, they have a guided regulation capacity of the HLB balance through the change of the medium degree of oligomerisation ( ) of the polyoxyethylene chain (PEO). Can thus obtain a wide range of structures such as micellar solute, dispersion, emulsion, and foaming agents, etc., through the cyanoethylation of polyethoxylated nonylphenols with a medium degree of oligomerisation ( ) between 3 and 20 structural oxyethylene units (EO) in alkaline catalysis with monomer acrylonitrile, followed by a classical hydrogenation in heterogeneous catalysis of intermediary nitrile thus obtained, and finally partial hysrolysis and salefied with HCOOH; CH3COOH. These are biodegradable in water plants, which ensure special ecologlcal features and high compatibility within the restrictive legal ensemble of a foodstuff processing integrated in an extremely polluted environment. Structures have real bacteriostatical abilities compared to a wide spectrum of microrganisms (tested in studies related to this paper). Low toxicity of polyoxyethylene chains (PEO) together with that of other structural units in this polyether primary amides provide the studied glymes with a high compatibility in relation to environment and to plant and animal organisms of the food chain.


2021 ◽  
Author(s):  
Yueting Xu ◽  
Yanfei Zhao ◽  
Fengtao Zhang ◽  
Yuepeng Wang ◽  
Ruipeng Li ◽  
...  

Alcoholysis of propylene oxide is achieved over azolate ionic liquids at room temperature by hydrogen-bonding catalysis, accessing glycol ethers in moderate to high yields with selectivity of >99%.


2020 ◽  
Vol 22 (16) ◽  
pp. 9074-9085 ◽  
Author(s):  
Thamires A. Lima ◽  
Vitor H. Paschoal ◽  
Rafael S. Freitas ◽  
Luiz F. O. Faria ◽  
Zhixia Li ◽  
...  

The THz dynamics of ionic liquids based on tetraalkylammonium cations were investigated by a combined usage of inelastic neutron scattering (INS), Raman, and far-infrared (FIR) spectroscopies and the power spectrum calculated by molecular dynamics (MD) simulations.


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