Chloroacetamide Research Articles (Page 1)

Chloroacetamides (CAAs) are an important class of synthetic herbicides long utilized in agriculture for their strong weed-control efficacy. However, their environmental and health impacts have raised significant concerns. Therefore, both the structural modification of known active compounds and the identification and design of new compounds with desirable properties and biological activity represent a significant challenge in pesticide chemistry. The bioactivity parameters of 18 new chloroacetamide derivatives were evaluated by using both in silico and chromatographic approaches. Correlation of chromatographic parameters with software-derived logP and EC50 values by linear regression analysis identified key structural factors affecting their lipophilicity and potential toxicity to non-target organisms. Multivariate analysis revealed and quantified that the total number of carbon atoms in the molecule (determines lipophilicity), along with the chemical nature of the hydrocarbon substituent (affects water solubility), plays a major role in shaping the biological profile of the tested derivatives. Moreover, it was found that the number of rotatable bonds significantly influences their toxicity. Furthermore, the results show that chromatographic parameter RM 0 can serve as an alternative measure of lipophilicity, while the parameter m can indicate toxicity of the analyzed CCAs'.

The reduction and alkylation steps are crucial in shotgun proteomics sample preparation to ensure efficient protein digestion and prevent the reformation of artefactual disulfide bonds following proteolysis. Excessive alkylation reagents can lead to overalkylation side reactions, compromising the quality of proteomics sample detection. Previous research has predominantly focused on comparing the effects of various types or concentrations of reducing agents or alkylating reagents for proteomic sample preparation. However, there is a lack of studies systematically comparing the utilization of quenching agents for alkylation reactions and investigating their specific impact on tryptic digestion activity in proteomics sample preparation under conditions of excessive alkylation reagents. In this study, we comprehensively compared the impacts of three different alkylation quenching methods (including cysteine quenching, dithiothreitol [DTT] quenching, and no quenching) on proteomic sample preparation. The upstream sample processing included reduction with DTT or tris(2-carboxyethyl)phosphine (TCEP), followed by alkylation with iodoacetamide (IAA) or chloroacetamide (CAA). Our study demonstrates that the choice of quenching method significantly affects the number of identified proteins and peptides, missed cleavage rates at lysine or arginine residues during trypsin digestion, and the occurrence of overalkylation side reactions. Importantly, our findings indicate that cysteine quenching effectively preserves trypsin activity, ensuring high-quality protein sample preparation. This study provides a systematic analysis of various alkylation quenching methods in proteomic sample preparation and offers optimized experimental protocols and valuable data references for proteomics studies.

This study explores the utilization of natural compounds, including zinc oxide (ZnO) derived from aloe vera, chitosan, and pandan leaves (Pandanus amaryllifolius Roxb) extract, for the development of antimicrobial-coated fabric textiles. The objectives of this research are to optimize the formulation, structural properties, and antimicrobial effectiveness of these textiles through comprehensive characterization techniques, including Fourier Transform Infrared Spectroscopy (FTIR), Particle Size Analysis (PSA), and Scanning Electron Microscopy-Energy Dispersive X-ray Spectroscopy (SEM-EDX). The addition of NaOH as a base at pH 13.0 played a crucial role in obtaining smaller particles with improved homogeneity. The XRD analysis confirmed the hexagonal crystalline structure of ZnO in the composite. The use of Chloroacetamide (CAA) binder and NaOH in different molar compositions influenced the coating of ZnO-Chitosan/Pandan leaf on cotton fibers. A molar ratio of 1:2 for CAA and NaOH resulted in the most substantial reduction in the intensity of the carbonyl absorption peak in the FT-IR spectrum, indicating a more complete and robust coating.

By reacting AlCl3 with chloroacetamide (CA) at the optimal mole ratio (2:1), a new type of ionic liquid was created in addition to the group of ionic liquids (aluminum chloride-amide). With an ionic conductivity of 0.34 mS/cm, the resultant clear brown ionic liquid demonstrated good thermal stability at ambient temperature in a glove box filled with nitrogen gas. Its coordination was established using FT-IR. Measurements have been made of additional physical characteristics including viscosity and cyclic voltammetry.

Disinfection byproducts (DBPs) cause endocrine disruption via estrogenic or anti-estrogenic effects on estrogen receptors. However, most studies have focused on human systems, with little experimental data being presented on aquatic biota. This study aimed to compare the effects of nine DBPs on zebrafish and human estrogen receptor alpha (zERα and hERα). In vitro enzyme response-based tests, including cytotoxicity and reporter gene assays, were performed. Additionally, statistical analysis and molecular docking studies were employed to compare ERα responses. Iodoacetic acid (IAA), chloroacetonitrile (CAN), and bromoacetonitrile (BAN) showed robust estrogenic activity on hERα(maximal induction ratios of 108.7%, 50.3%, and 54.7%, respectively), while IAA strongly inhibited the estrogenic activity induced by 17β-estradiol (E2) in zERα (59.8% induction at the maximum concentration). Chloroacetamide (CAM) and bromoacetamide (BAM) also showed robust anti-estrogen effects in zERα (48.1% and 50.8% induction at the maximum concentration, respectively). These dissimilar endocrine disruption patterns were thoroughly assessed using Pearson correlation and distance-based analyses. Clear differences between the estrogenic responses of the two ERαs were observed, whereas no pattern of anti-estrogenic activities could be established. Some DBPs strongly induced estrogenic endocrine disruption as agonists of hERα, while others inhibited estrogenic activity as antagonists of zERα. Principal coordinate analysis (PCoA) showed similar correlation coefficients for estrogenic and anti-estrogenic responses. Reproducible results were obtained from computational analysis and the reporter gene assay. Overall, the effects of DBPs on both human and zebrafish highlight the importance of controlling their differences in responsiveness for estrogenic activities including the water quality monitoring and endocrine disruption, as DBPs have species-specific ligand-receptor interactions.

In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β–oxoanilides as readily obtainable compounds. In this study, treatment of 3-Oxobutanamides 1 with phenyl isocyanate at room temperature in basic medium and DMF afforded thiocarbamoyl derivative 3 through intermediate 2 upon treatment with dilute HCl. The non-isolable potassium salt 2 was allowed to react with α-halo carbonyl compounds such as ethyl chloroacetate and chloroacetonitrile in dry DMF at room temperature to furnished thiophene 6 and thiazole derivative 9 respectively. Compound 6 was treated with hydrazine hydrate in ethanol to yield thiophene-5-carbohydrazide derivative 7. Also, compound 1 reacted with malononitrile and sulfur element in refluxing absolute ethanol and triethylamine to yield thiophene derivative 11, which reacted with formic acid and α-chloro acetylchloride to give thieno[2,3-d]pyrimidine derivative 12 and chloro acetamide derivative 13. Treatment of compound 13 with ammonium thiocyanate led to thiazolo[3,2-a]thieno[2,3-d]pyrimidine derivative 15 through non-isolable 14. Also, condensation of 1 with malononitrile and ethylene diamine afforded the pyridine derivative 17 and 1,4-diazepine derivative 18. The structures and formulas of all the synthesized compounds were supported by spectral data. Some of the synthesized compounds were evaluated for their antibacterial and antioxidant activity. These compounds showed different degrees of activity.

Abstract A string of novel heterocyclic mono azo dyes were synthesized and their utilization in dyeing different fabrics as wool and nylon were discussed. Thienopyridine azo dyes 4 and 6were prepared by reaction of chloro acetamidederivative 2 with diamino compounds to yield 3 and 5, followed by reaction with NaNO2/HCl and coupling with nucleophilic reagent. One‐pot reaction of chloro acetamide 2 with ammonium thiocyanat in solvent ethanol gave the unexpected thienopyrimidine derivative 7, which contain two active sites, the former is primary amine that was able to form diazonium salt that coupled with N,N‐dimethylaniline, resorcinol, and/or self‐coupling to afford the azo dyes 8‐10, and the latter is active methylene group that underwent coupling with different diazonium salts to give the azo thienopyrimidine derivative dye 11‐15. The dyeing performance of these azo dyes had been investigated in terms of their dyeing behavior and fastness properties on different fabrics. Results showed that the color strength (K/S) values, as well as, washing, rubbing, and resistance to acid, alkali and light showed high efficiency of these heterocyclic mono azo dyes to dye wool rather than nylon fibers.

Weak magnetic field accelerates chloroacetamide removal by zero-valent iron in drinking water

Aim. Optimization of reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles. Materials and methods of research. The methods of organic synthesis, instrumental methods of organic compound analysis were used. Results. A scheme for the synthesis of 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles by the interaction of 5-amino-4-arylsulfonyl-3-methylthiopyrazoles 1a-b with chloroacetone, phenacyl bromide and 2-chlorocyclohexanone was developed. In contrast to the previously described interaction of substituted 5-aminopyrazoles with chloro (N-aryl) acetamides proceeding exclusively with the release of N 1 -alkylation products, in this reaction a mixture of N 1 - and N 2 -isomeric alkylation products is formed. The ratio of isomers depends on the nature of the reagents and, according to the 1H NMR-spectroscopy, is about 60:40 %.The developed technique allows with one of the synthetic procedure to carry out N 1 -alkylation of 5-aminopyrazoles 1a-b and the cyclization of products 2 in imidazo[1,2-b]pyrazoles 4a-c without isolating the N 2 -alkylation product. The purity of the obtained compounds is proved chromatographically, the structure is confirmed by the data of 1H NMR-spectroscopy. Conclusions. Optimized reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles for targeted synthesis of the novel agents for the pharmaceutical practice

Chloroacetamide (CAA) is a preservative used in various cosmetic, personal care and household products. Due to the hazard potential for allergic reaction and reproductive toxicity, CAA is being considered a high priority for screening assessment and toxicological re-evaluation. This study describes the development of a highly specific and sensitive atmospheric pressure chemical ionization tandem mass spectrometry method for the determination of CAA in rat plasma and its application to a topical bioavailability study. Chromatographic separations were achieved on a C8 column using a highly aqueous mobile phase with a binary gradient elution. The assay was linear in the concentration range of 5-2,500 ng/mL (r ≥ 0.995) using a small sample volume (100 µL). Applicability of the assay was demonstrated in a bioavailability study in rats after i.v. injection (0.5 or 2 mg/kg) and topical application (7.02 mg/kg). Average elimination half-life and clearance ranged from 26.6 to 30.5 min and 53.9 to 57.3 mL/min/kg, respectively. Upon topical application, CAA was slowly but steadily absorbed for a prolonged time period (12 h). The topical bioavailability was 53.5 and 48.3% for emulsion and lotion, respectively. The developed assay may be useful to examine the relationship between exposure and toxic potential of CAA in risk assessment.

A novel series of selenolo [2, 3-b] tetrahydroquinoline derivatives were synthesized by the reaction of NaSeH with 2-chloro-3-cyano-4-(4-methoxyphenyl)-5, 6, 7, 8-tetrahydroquinoline 2 followed by reactions with chloro acetone, chloro acetonitrile, ethyl chloroacetate and chloro acetamide to yield 9 and 11a-c respectively. Reactions of 11c with acetic anhydride, cyclohexanone and aromatic aldehyde affording derivatives 12-14 respectively. Spectroscopic (IR, 1HNMR, 13CNMR and MS) were confirmed the structure of the synthesized compounds. Compounds 5a-c, 9, 11a-c, 12, 13 and 14 were investigated for their anti-inflammatory and analgesic activities; in addition, the most active compounds were tested for their acute toxicity. Keywords : Tetrahydro Quinolines; Pharmacological Screening; Pyrimidoselenolo Tetrahydroquinolines; Spirocyclohaxanepyrimidoselenolo Tetrahydroquinoline.

A new series of selenolo[2,3-b]quinoline, pyrimido[4′,5′:4,5]selenolo[2,3-b]quinoline, pyrimido[4′,5′:4,5]selenolo[2,3-b]-[1,2,4′triazolo[1,5-c]quinoline, and pyrimido[4′,5′:4,5]selenolo[2,3-b][1,2,4]triazolo[4,3-c]quinoline derivatives were prepared starting from diquinolinyl diselenide or 3-cyano-4-methylquinoline-2(1H)selenone with chloro acetonitrile or chloro acetamide. Elemental analysis, IR, 1H NMR, 13C NMR, and mass spectral data confirmed the structure of the newly synthesized compounds. In addition, the most active compounds were tested for their acute toxicity. Moreover, some of the tested compounds were screened for their antibacterial and antifungal activities. The minimum inhibitory concentration (MIC) of the most active compounds was 100 mg mL−1. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Abstract Herbicidal chloroacetamides cause a very sensitive inhibition of fatty acid incorporation into an insoluble cell wall fraction of Scenedesmus acutus. The molecular basis was investigated in more detail. After incubation of the algae with [14C]oleic acid and saponification, the remaining pellet was solubilized and fractionated consecutively with chloroform / methanol, phosphate buffer, amylase, pronase, and finally with dioxane/HCl. By acid hydrolysis in dioxane a part of the cell wall residue was solubilized showing inhibition of exogenously applied oleic acid and other labelled precursors such as stearic acid, palmitic acid, and acetate. After extraction of this dioxane-soluble subfraction with hexane, HPLC could separate labelled metabolites less polar than oleic acid. T heir formation was completely inhibited by chloroacetam ides, e.g. 1 μᴍ metazachlor. This effect was also observed with the herbicidally active 5-enantiomer of metolachlor while the inactive R-enantiomer had no influence. These strongly inhibited metabolites could be characterized by radio-HPLC /MS as very long chain fatty acids (VLCFAs) with a carbon chain between 20 and 26. Incubating am etazachlor-resistant cell line of S. acutus (Mz-1) with [14C]oleic acid, V LCFA s could not be detected in the dioxane/ HCl-subfraction. Furthermore, comparing the presence of endogenous fatty acids in wildtype and mutant Mz-1 the VLCFA content of the mutant is very low, while the content of long chain fatty acids (C16 -18) is increased, particularly oleic acid. Obviously, the phytotoxicity of chloroacetam ides in S. acutus is due to inhibition of VLCFA synthesis. The resistance of the mutant to metazachlor has a bearing on the higher amount of long chain fatty acids replacing the missing VLCFAs in essential membranes or cell wall components.

Resting cell suspensions of the soil methylotroph Methylosinus trichosporium OB-3b rapidly metabolize acetonitrile (ACN) and chloroacetonitrile (CCN) to bicarbonate. Formate, a natural substrate for this organism, is a major metabolite in both cases. The first step in these processes, established with 13C-labeled substrates and NMR analysis, is an oxygen insertion into the C−H bond to yield the corresponding cyanohydrins. With acetonitrile, the loss of HCN from the initially formed cyanohydrin (HOCH2CN) produces formaldehyde. The latter is rapidly converted to formate and CO2. With chloroacetonitrile, the first formed cyanohydrin [HOCHCl(CN)] may lose HCN to produce formyl chloride or lose HCl to yield formyl nitrile. The generation of CO, in addition to formate, implicates formyl chloride and/or formyl nitrile as intermediates. With neither ACN nor CCN is the nitrile moiety directly attacked or hydrolyzed. In particular, the nitrile hydrolysis products from CCN, chloroacetamide (CAM), and chloroacetic acid (CA) are not detected. In addition, hydrolysis of the C−Cl moiety of CCN does not occur. In contrast, incubation of CAM and CA with this organism does result in the corresponding hydroxy amide and acid directly. The slower dehalogenation of the amide and acid entail a direct microbial hydroxylation of the C−Cl bond. Based upon this study and related work with methylene and ethylene halides, it may be concluded that in the series ClCH2X (X = Cl, Br, CN) oxygen insertion is the initial step in dehalogenation by this organism. However, in the series ClCH2Y (Y = CH2Cl, CO2H, CONH2), the dehalogenation is the result of a direct hydrolysis of the C−Cl bond. This organism also transforms cyanide ion, but incubations with K13CN resulted in no detectable products.

Establishing the general reactivity of any segment of the terrestrial environment can be an important means of characterizing it. The sites capacity for transformation may reflect its environmental health, and knowing this capacity can provide a basis for estimating the rates and nature of the transformations that may occur there. However, no direct means for measuring this reactivity has been available. This work expands upon preliminary efforts to develop reactivity probes for the environment. The 13C-labeled compounds chloroacetic acid (CA), chloroacetamide (CAM), and chloroacetonitrile (CCN) have been synthesized and tested as site reactivity probes (SRPs). The reactivity of activated sludge, a dump site soil, coastal marine water and sediments, and lake water and sediments was assessed by the probes. A simple protocol for employing the SRPs entails incubation with a 2-mL slurry, centrifugation/filtration at a desired time, followed by direct NMR analysis of products. The results indicate a broad capa...

A new allergen responsible for shoe allergy: chloroacetamide

Chloroacetamide photocyclization. Synthesis of 20-deethylcatharanthine

Herbicidal activitiy of chloroacetamides and pyridazinones on sugarbeets and weeds

Notes - Reactions of <i>unsym</i>-Dimethylhydrazine with Acrylonitrile and with Chloroacetamide