Thioacetic Acid Research Articles

Some Novel Series of 3-Alkylidene 3-Phenylthio-3-Chloro Azetidine -2-One Were Synthesized by The Staudinger Ketene-Imine Cycloaddition and Evaluation of Their Biological Activity

Various series of 3-alkylidene 3-Phenylthio-3-Chloro azetidine -2-one(5) synthesized by reaction of 1- (4'-Methoxyphenyl)-3-chloro-3-phenylthio-4,4-diethoxycarbonylazetidin-2-one (4) with thionyl chloride taking MDC as solvent while synthesis of Compound 4 carried out the reaction between phenyl thio acetic acid and N-(4-Methoxyphenyl)-1,1-diethoxycarbonylimine (2) while compound second synthesized by staring material diethyl keto malonate and p-anisidine. these newly synthesized compound were evaluate using different analytical tools These compounds were also evaluated for their anti- inflammatory and analgesic activities.

Synthesis, Characterization, and Antimicrobial Evaluation of Thiadiazole Derivatives Derived from 2-Amino-5-Thio-1,3,4-Thiadiazole

This manuscript introduces a series of novel Schiff base and heterocyc-licring compounds, focusing on derivatives of 1,3-oxazepine and thiazo-lidinone.The derivative (2-Hydroxy-N-(5-mercapto-[1,3,4] thiadiazol-2-yl)-2-phenyl-acetamide was created by reacting ethyl mandelate ester[M1] and 2-amino-5-thio-1,3,4-thiadiazole compound to produce new compound [M2] and after that, compound [M2] was reacted with hydrazine hydrate 99% in dry DMF solvent, yielding the compound (N-(5-Hydrazino-[1,3,4]thiadiazol-2-yl)-2-hydroxy-2-phenyl-acetamide [M3]. In contrast , the Schiff base compound [M4] were synthesized by reacting compound [M3] with aromatic heterocyclic aldehyde (furan-2-carbaldehyde) in the presence of glacial acetic acid as a catalyst, and then Schiff base [M4] was reacted with maleic anhydride in dry benzene as a solvent to produce (1,3-Oxazepine) derivative [M5]. Additionally, the thiazolidinone derivative [M6] was synthesized through the reaction of equimolar amounts of (N-[5-(N'-Furan-2-yl-methylene-hydrazino)-[1,3,4]thiadiazol-2-yl]-2-hydroxy-2-phenyl-acetamide [M4] with thioacetic acid compound in chloroform as a solvent. The structural formula of all derivatives was confirmed by FT-IR and (1HNMR, 13CNMR) spectroscopy. The synthesized derivatives [M1-M6] were screened for their evaluated for antibacterial activity against S. aureus, S. epidermidis, E. coli, Klebsiella sp., and the fungus Candida albicans. Dimethyl sulfoxide (DMSO) was used as the solvent. Also, the ampicillin compound was used as the standard drug for comparison.

Aluminum complexes with sulfur containing pyridine based ligands: Synthesis, structure and catalysis

New pyridinyl SN-bi- (1) and SNS-tridentate (3) ligands were obtained by hydrothiolation of substituted alkenes with thioacetic acid. A number of these, as well as the known SN- (2) and SNO- (4, 5) ligands were used in the synthesis of methylaluminum complexes. Molecular structure of the monoligand, [2,6-MePy(CH2CMe2S)]AlMe2 (1a), [2,6-MePy(CH2CH2CMe2S)]AlMe2 (2a), [2,6-Py(CH2CMe2S)2AlMe] (3a) and [2,6-Py(CH2CH2CMe2SH)(CH2CH2CMe2O)AlMe2]2 (5a), and the diligand, [2,6-MePy(CH2CMe2S)]2AlMe (1b), complexes were studied in solution (NMR spectroscopy) and in crystal (1a, XRD); the dependence between the ligand and the complex structure formed was established. The catalytic activity of 1-3a, 5a and 1b in the ring-opening polymerization of ε-caprolactone was studied in bulk, indicating high control of the process.

Direct Synthesis of α-Ketothioamide Derivatives through a One-Pot Reaction of Sulfur Ylides, Nitrosobenzenes, and Thioacetic Acid.

A one-pot approach has been developed for the synthesis of α-ketothioamide derivatives from sulfur ylides, nitrosobenzenes, and thioacetic acid. This protocol is carried out under mild reaction conditions in generally moderate to excellent yields without any precious catalysts, affording the derivatives with structural diversity. Additionally, a possible mechanism for this chemical transformation is proposed.

New Protocol for the Synthesis of S-Thioesters from Benzylic, Allylic and Tertiary Alcohols with Thioacetic Acid.

A new one-pot solvent-less reaction to convert benzylic, allylic, ferrocenyl or tertiary alcohols into S-thioesters, bench-stable and less odorous precursors of the corresponding thiols, which is based on reactions in neat thioacetic acid in the presence of tetrafluoroboric acid, is presented. Reaction monitoring by NMR and GC of the benzyl alcohol conversion indicated the intermediate formation of benzyl acetate and benzyl thionoacetate (PhCH2 OC(S)CH3 ) prior to the slower conversion to the final S-benzyl thioacetate product. Increasing the HBF4 concentration enhanced the reaction rate, giving good to excellent yield (up to 99 %) for a large scope of alcohols. Control experiments, with support of DFT calculations, have revealed a thermodynamically favorable, though requiring HBF4 -activation, disproportionation of CH3 C(O)SH to CH3 C(O)OH and CH3 C(S)SH, the latter immediately decomposing to H2 S and (MeC)4 S6 but also generating the hitherto unreported [MeC(O)C(Me)S]2 (μ-S)2 . Kinetic investigations demonstrated that the rate of benzyl alcohol conversion is second-order in [PhCH2 OH] and second order in [HBF4 ], while the rate of conversion of the benzyl acetate intermediate to S-benzyl thioacetate is second order in [PhCOOMe] and fourth order in [HBF4 ]. The DFT calculations rationalize the need to two alcohol molecules and two protons to generate the reactive benzyl cation.

Synergistic Activation of Nitrite and Thiocarbonyl Compounds Affords NO and Sulfane Sulfur via (Per)thionitrite (SNO- /SSNO- ).

(Per)thionitrite (SNO- /SSNO- ) intermediates play vital roles in modulating nitric oxide (NO) and hydrogen sulfide (H2 S) dependent bio-signalling processes. Whilst the previous preparations of such intermediates involved reactive H2 S/HS- or sulfane sulfur (S0 ) species, the present report reveals that relatively stable thiocarbonyl compounds (such as carbon disulfide (CS2 ), thiocarbamate, thioacetic acid, and thioacetate) react with nitrite anion to yield SNO- /SSNO- . For instance, the reaction of CS2 and nitrite anion (NO2 - ) under ambient condition affords CO2 and SNO- /SSNO- . A detailed investigation involving UV/Vis, FTIR, HRMS, and multinuclear NMR studies confirm the formation of SNO- /SSNO- , which are proposed to form through an initial nucleophilic attack by nitrite anion followed by a transnitrosation step. Notably, reactions of CS2 and nitrite in the presence of thiol RSH show the formation of organic polysulfides R-Sn -R, thereby illustrating that the thiocarbonyls are capable of influencing the pool of bioavailable sulfane sulfurs. Furthermore, the availability of both NO2 - and thiocarbonyl motifs in the biological context hints at their synergistic metal-free activations leading to the generation of NO gas and various reactive sulfur species via SNO- /SSNO- .

Synergistic Activation of Nitrite and Thiocarbonyl Compounds Affords NO and Sulfane Sulfur via (Per)thionitrite (SNO−/SSNO−)

Abstract(Per)thionitrite (SNO−/SSNO−) intermediates play vital roles in modulating nitric oxide (NO) and hydrogen sulfide (H2S) dependent bio‐signalling processes. Whilst the previous preparations of such intermediates involved reactive H2S/HS− or sulfane sulfur (S0) species, the present report reveals that relatively stable thiocarbonyl compounds (such as carbon disulfide (CS2), thiocarbamate, thioacetic acid, and thioacetate) react with nitrite anion to yield SNO−/SSNO−. For instance, the reaction of CS2 and nitrite anion (NO2−) under ambient condition affords CO2 and SNO−/SSNO−. A detailed investigation involving UV/Vis, FTIR, HRMS, and multinuclear NMR studies confirm the formation of SNO−/SSNO−, which are proposed to form through an initial nucleophilic attack by nitrite anion followed by a transnitrosation step. Notably, reactions of CS2 and nitrite in the presence of thiol RSH show the formation of organic polysulfides R‐Sn‐R, thereby illustrating that the thiocarbonyls are capable of influencing the pool of bioavailable sulfane sulfurs. Furthermore, the availability of both NO2− and thiocarbonyl motifs in the biological context hints at their synergistic metal‐free activations leading to the generation of NO gas and various reactive sulfur species via SNO−/SSNO−.

Activated cyanoacetamide in heterocyclic synthesis: Design, synthesis, antitumor activity and docking study of some new pyrimidine derivatives

The precursor cyanoacetamide derivatives (6) were achieved by the reaction of pyrimidine derivative 5 with cyanoacetic acid catalyzed by acetic anhydride. The reaction of cyanoacetamide derivative 6 with different reagents afforded many heterocyclic systems such as thioacetic acid (9), dithiolane derivatives (11) and (12), 1,8-naphthyridine (14), quinoline derivatives (17) and (18), pyridine derivatives 20, 22, 24, 26, and 27, pyridazine (30), pyranopyrimidine (32), and pyrazolopyrimidine (34). All the newly synthesized compounds were characterized with spectroscopic analyses. Compounds were tested for their anticancer activity against three human cancer cell lines: hepatocellular carcinoma (HepG-2), colon cancer (HCT-116), and mammary gland breast cancer (MCF-7). The studied compound's cytotoxic activity ranged from very strong to very weak. The most active compounds were 9, 10, 11, 27, and 34. The binding disposition of the docked compounds, in particular 9, 10, 11, 27, and 34, towards the binding site of AKT complexed with co-crystallized ligand was investigated using molecular docking (PDB = 4EJN).

Thioxanthonation of 2-naphthalene-thioacetic acid as a visible-light photoinitiator: The investigation of photophysical and photochemical properties

Thioxanthonation of naphthalene thioacetic acid (TXNPSCH2COOH) resulted a visible light photoinitiator with the high molar absorptivity (ε405: 5680 L.mol−1.cm−1) in the visible spectral region and made this compound an attractive photoinitiator for free radical polymerization reactions. Low fluorescence quantum yield (ΦF: 0.06 in 2-MeTHF) and comparatively low triplet energy (186 kJ/mol in 2-MeTHF) was in favorable for efficient intersystem crossing to the triplet state which is necessary for production of initiating radicals. Indeed, photopolymerization of methyl methacrylate along with TXNPSCH2COOH (1 × 10−3 M) and a tertiary amine namely MDEA yielded nearly 25% conversion of monomer to polymer. All spectrophotometric studies including laser flash photolysis which gives triplet lifetime of initiator which is very important information for initiation mechanism of photoinitiators, indeed a long enough triplet lifetime of TXNPSCH2COOH (τT: 1000 ns) allows for efficient reactions with co-initiators to generate radicals.

One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid

The direction of the reaction between substituted perfluorobenzenes and thioacetic acid depends on the location of the substituents in perfluoroaromatic ring. Hexafluorobenzene reacts at positions 1 and 4, perfluoro-m-xylene reacts at positions 4 and 6, while perfluoroindane reacts at positions 5 and 6 to give the corresponding dithiols with para-, meta- and ortho-location of the thiol groups, respectively. Domino-reaction of perfluoroindane-5-thiol and its acetyl thioester affords hexadecafluoro-2,12-dithia-pentacyclo[11.7.0.03,11.05,9.015,19]icosa-1(13),3,5(9),10,14,19-hexaene

Influence of organic acids on locomotor activity of Stratiolaelaps scimitus (Mesostigmata, Laelapidae)

Increasing the activity of zoophage Acari in agrocenoses, for example luring them to concentrations of harmful insects, could be effectively performed using attractants, for example organic acids that people use in households and industry. In our experiment, we studied the influence of organic acids on the locomotor activity of Stratiolaelaps scimitus (Womersley, 1956) (Mesostigmata, Laelapidae). Different organic acids caused certain reactions in those zoophages. Acetic acid encouraged this mite to activity and attracted it, while thioacetic acid inhibited and repelled it. Fatty acids such as tridecylic and oleic acids had an activating effect on the locomotor activity of S. scimitus. Three isomers of valeric acid inhibited locomotor activity, and the mites exerted negative chemostasis to them. Maximum locomotor activity of the mites was observed when using asparagine, ornithine, propionic acid, tridecanoic acid, boric acid, and arginine. Locomotor activity of the mites was inhibited by 3,3-dimethylbutanoic acid, thioacetic acid, pivalic acid, maleic acid, formic acid, succinic acid, 2-methylbutanoic acid, isovaleric acid, 6-aminohexanoic acid, and 2-oxoglutaric acid. We propose using attractiveness coefficient and coefficient of migratory activity, which reflect the effects of aroma compounds on mites. Those coefficients are helpful in identification of a behaviour model for mites exposed to aroma compound: attack, motionless state or escape. High attractiveness and migratory-activity coefficients mean attack on victim; low coefficients indicate motionless mites; high migratory activity and low attractiveness coefficient mean escape reaction. Our results indicate complexity of behaviour reactions of mites, which were sensitive to volatile chemical compounds in the environment. We found a high potential of using those compounds in attracting zoophages during their introduction in agrocenoses of greenhouses and open plots.

Synthesis of Three Novel Silane-Based Carboxylic Acids for Application in Methacrylated Epoxy-Based Oligomers and Their Ability to Improve the Properties of UV Curable Hybrid Coatings

Improvement of thermal stability of silicone-based coatings was the main objective of this study. In this study bromoacetic acid (BAA) was reacted with 3-(mercaptopropyl) trimethoxy silane (MPTS) and trimethoxy silyl propyl thioacetic acid (TSTA) was produced. Also, bromoacetic acid (BAA) was reacted with 3-(triethoxysilyl) propylamine (APTS) and triethoxysilyl propylamino acetic acid (TSPA) was synthesized. Finally, from a reaction between trimellitic anhydride (TMA) and APTS, trimellitylimidopropyl triethoxysilane (TMIS) resulted. Compounds containing carboxylic acids and trimethyl silane were obtained in all of these reactions. Furthermore, hybrid coatings based on methacrylated bisphenol A epoxy (MBAE) and the synthesized carboxylic acids were obtained by photopolymerization. Polycarbonate substrates were utilized for preparation of the transparent hybrid films. Then the solvent resistance, hardness and gel content, as well as the adhesion of the coatings, were measured as physical and mechanical properties. According to the obtained results, these properties of the hybrid coatings were improved with the increase in alkoxysilanes and sol–gel precursor contents. The surface morphology was characterized by scanning electron microscopy (SEM). The results showed that silica particles were not dispersed homogenously at the molecular level in the hybrid system. Also, the thermogravimetric analysis results indicated that alkoxysilanes enhanced the thermal oxidative stability of the hybrid coatings.

Gas Phase Reaction of Ketene with H2S in Troposphere: Catalytic Effects of Water and Ammonia

Background: Additions of water monomer (H2O) to simplest ketene, i.e., H2C=C=O (mentioned as ketene, henceforth) in the Earth's atmosphere results in the formation of acetic acid. However, this reaction is not feasible under tropospheric conditions due to the high reaction barrier amounting to nearly 40 kcal mol-1. A Significant reduction of the barrier height (below 20 kcal mol-1) is achieved upon addition of another H2O molecule as a catalyst. It is worth mentioning that like H2O and ammonia (NH3), H2S could also play an important role in the “loss mechanism” of various atmospherically important species such as ketones and aldehydes. Aims: This study aims to get insight into the energetics and kinetics of a reaction between ketene and H2S in the troposphere which has not been done before. Objective: Due to close similarity of H2O and H2S, studying the sulfolysis reaction between ketene and H2S could provide some interesting insights into the nature of various hydrogen bonded complexes of ketene as well as the impact on the products formed under the atmospheric conditions. Methods: The water and ammonia catalyzed gas-phase addition reactions of ketene with H2S has been investigated using CCSD(T)-F12a/cc-pVTZ-F12a//M06-2X/6-311++G** level of theory. In this study, rate constants for all possible reaction channels are calculated using transition state theory. Results: It is found that, under tropospheric conditions at 298 K and 1 atm, the rates via catalyzed reaction channels are significantly faster than those via uncatalyzed reactions. Between the two catalysts, ammonia acts as far better catalyst than water for this reaction. However, since the concentration of water is significantly larger than ammonia, the effective rate of water catalyzed reaction becomes higher than that of ammonia catalyzed reaction. Combustion is a major source of ketene in atmosphere. Under combustion conditions such as in the presence of air and at or above ignition temperature, the ammonia catalyzed channel is faster below 1500 K, while the uncatalyzed reaction channel becomes faster above that temperature. Conclusion: Results from the present study show that the barrier for thioacetic acid formation through uncatalyzed sulfolysis of ketene via faster C=O addition pathway is substantially high as 40.6 kcal mol-1. The barrier height of the two transition states TS1 and TS2 are 19.7 and 13.8 kcal mol-1 for water catalyzed reaction and 14.4 and 7.2 kcal mol-1 for ammonia catalyzed reaction. Thus, ammonia has appreciably lowered the barrier height compared to water as catalyst. It has been observed that the hydrolysis reaction is more probable than the sulfolysis reaction under atmospheric conditions in the troposphere, but the ammonia catalysed sulfolysis is the fastest one at 298 K. The effective rate constant of the water catalysed hydrolysis reaction is found to be more than the ammonia catalysed reaction due to the higher monomer concentration of water than ammonia. Ammonia catalyzed reaction rate increases monotonously with increasing temperature. Further rate coefficient for uncatalyzed reaction is found to be dominant under combustion conditions, i.e., above 1500 K.

Interaction between Cu and Thiols of Biological and Environmental Importance: Case Study Using Combined Spectrophotometric/Bathocuproine Sulfonate Disodium Salt Hydrate (BCS) Assay.

Considering the biological and ecological importance of Cu-thiol interactions and the discrepancies in previous research, this study focuses on Cu interactions with biologically and ecologically relevant thiols: glutathione (GSH), L-cysteine (L-cys), 3-mercaptopropionic acid (MPA), and thioacetic acid (TAA) in aqueous solution. The addition of Cu(II) to a thiol-containing solution led to a rapid reduction of Cu(II) and the formation of a Cu(I)-thiol complex. The mechanism of Cu(II) reduction and Cu(I) complex formation as well as the kinetics of Cu(I) oxidation strongly depend on the structural properties of the individual thiols investigated. The reducing power of the investigated thiols can be summarized as follows: L-cys ≅ GSH > MPA > TAA. The reaction order, with respect to Cu(I) oxidation, also changes over the time of the reaction course. The deviation of the reaction kinetics from the first order with respect to Cu(I) in the later stages of the reaction course can be attributed to a Fenton-like reaction occurring under low thiol concentration conditions. At high Cu:thiol ratios, in the case of GSH, L-cys, and MPA, the early stage of the reaction course is characterized by high Cu(I) stability, most likely as a result of Cu(I) complexation by the thiols present in excess in the reaction mixture.

Serendipitous late-stage modification of dipeptide by using AIBN and thioacetic acid

Post-assembly peptide modifications have become an integral part of medicinal chemistry nowadays. This exercise is useful in finding novel bioconjugates, therapeutic peptides and protein labelling. Therefore, in our attempts towards the modification of peptides, we have tried to insert thiophene moiety in dipropargyl dipeptide in the presence of AIBN and thioacetic acid. Surprisingly, instead of thiophene group introduction, we observe the serendipitous functionalization of amide group i.e. –NHCOCH3 is converted into –NHCHO group.

Condition-Controlled O-Acylation and N–O Bond Reduction of Hydroximic Acids with Thioacetic Acid

Condition-dependent transformations between hydroximic acids and thioacetic acid were achieved. Using NH4HCO3 in the ethanol solvent, efficient N-O bond cleavage of hydroxamic acids occurred to afford primary amides with high functional group compatibility. The reaction was switched to O-acylation when NEt3 and H2O were used as the base and solvent, respectively. These facile transformations could be scaled up to the gram level smoothly. Preliminary mechanistic studies suggested that the N-O bond cleavage involves a cascade process of acylation/reduction.

Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction

The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or a decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different reaction conditions. The use of solid Cs2CO3 leads unexpectedly to the synthesis of new D-A cyclopropane derivatives via a decyanation reaction, followed by diastereoselective acetylation, whereas the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, the use of tailored reaction conditions allows one to obtain either cyclic or open-chain products in moderate to good yields.

Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials

A series of poly(thiourethanes) (PTUs) from biobased monomers have been synthesized. Limonene and squalene were transformed into polyfunctional thiols by thiol-ene reaction with thioacetic acid and further saponification. They were then reacted in different proportions with hexamethylene diisocyanate (HDI) in the presence of a catalyst to prepare bio-based poly(thiourethane) vitrimer-like materials. The different functionalities of squalene and limonene thiols (six and two, respectively) allow for changing the characteristics of the final material by only varying their relative proportions in the reactive mixture. The proportions of thiol and isocyanate groups were stoichiometric in all the formulations tested. An acidic and a basic catalyst were tested in the preparation of the networked polymers. As the acidic catalyst, we selected dibutyltin dilaurate (DBTDL), and as the basic catalyst, a tetraphenylborate salt of 1,8-diazabicyclo(5.4.0)undec-7-ene (BGDBU), which has the advantage of only releasing the base at high temperatures. The materials obtained were characterized by thermogravimetry and thermomechanical analysis. The vitrimeric-like behavior was evaluated, and we could see that higher proportions of the limonene derivative in the formulations led to faster stress relaxation of the material. The use of the base catalyst led to a much shorter relaxation time. The materials obtained demonstrated good self-healing efficiency.

Chemical studies of chromanone-thiadiazole, pyridazine and thiosulfin hybrid

3-Chlorochromanon derivatives 4a,b are reacted with hydrazine hydrate to afford 3-hydrazino-2-tetrahydro(pyran or thiopyran)chroman-4-ones 5a,b. Then compound 5a,b is reacted with carbon disulfide and acetylacetone to give 5'-thiolo - 2-tetrahydro(pyrane or thiopyran)- spiro[chroman-3,2'- [1,3,4]-thiadiazole]-4-one 6a,b and 3', 5'-dimethyl- 2-tetrahydro(pyran or thiopyran) spiro [chroman-3,2'- piprazine]-4-one 7a,b, respectively. α-Chlorosulfenyl chlorides 2a,b are treated with thioacetic acid to form α-chloroalkyl disulfides 8a,b, the latter compounds 8a,b were treated with morpholine to furnish a mixture of 1,3,4-oxadithiins 9a,b, 1,3,4,5,6-oxatetrathiocins 10a,b, 1,2,4-trithiolanes 11a,b (cis- and trans-), 1,2,4,5-tetrathiins (cis- and trans-) 12a,b. The formation of the new compounds are confirmed by spectral (IR, 1H NMR, and MS) analysis.

Design, synthesis and screening of herbicidal activity for new phenyl pyrazole-based protoporphyrinogen oxidase-inhibitors (PPO) overcoming resistance issues.

Whilst there are several methods to control weeds, which continuously plague farmers around the globe, the application of small molecular compounds is still the most effective technology to date. Plants can evolve to become resistant to PPO-inhibitors, a class of herbicides in commercial use since the 1960s. It is therefore essential to continuously develop new herbicides based on this mode-of-action with enhanced intrinsic activity, an improved resistance profile and favourable physicochemical properties. Based on an Amaranthus PPO crystal structure and subsequent modelling studies, halogen-substituted pyrazoles have been investigated as isosteres of uracil-based PPO-inhibitors. By combining structural features from the commercial PPO-inhibitors tiafenacil and pyraflufen-ethyl and by investigating receptor-binding properties, we identified new promising pyrazole-based lead structures showing strong activity in vitro and in vivo against economically important weeds of the Amaranthus genus: A.retroflexus, and resistant A.palmeri and A.tuberculatus. The present work covers a series of novel PPO-inhibiting compounds that contain a pyrazole ring and a substituted thioacetic acid sidechain attached to the core phenyl group. These compounds show good receptor fit in line with excellent herbicidal activity against weeds that plague corn and rice crops with low application rates. This, in combination with promising selectivity in corn, have the potential to mitigate and affect weeds that have become resistant to some of the current market standards. Remarkably, some of the novel PPO-inhibitors outlined herein show efficacies against economically important weeds that were superior to recently commercialized and structurally related tiafenacil. © 2023 Society of Chemical Industry.