Herbicidal Activity Research Articles

Structure-Based Design, Virtual Screening, and Discovery of Novel Patulin Derivatives as Biogenic Photosystem II Inhibiting Herbicides.

Computer-aided design usually gives inspirations and has become a vital strategy to develop novel pesticides through reconstructing natural lead compounds. Patulin, an unsaturated heterocyclic lactone mycotoxin, is a new natural PSII inhibitor and shows significant herbicidal activity to various weeds. However, some evidence, especially the health concern, prevents it from developing as a bioherbicide. In this work, molecular docking and toxicity risk prediction are combined to construct interaction models between the ligand and acceptor, and design and screen novel derivatives. Based on the analysis of a constructed patulin-Arabidopsis D1 protein docking model, in total, 81 derivatives are designed and ranked according to quantitative estimates of drug-likeness (QED) values and free energies. Among the newly designed derivatives, forty-five derivatives with better affinities than patulin are screened to further evaluate their toxicology. Finally, it is indicated that four patulin derivatives, D3, D6, D34, and D67, with higher binding affinity but lower toxicity than patulin have a great potential to develop as new herbicides with improved potency.

Scalable Total Synthesis of Acremolactone B.

Acremolactone B is a pyridine-containing azaphilone-type polyketide. The first total synthesis of this molecule was achieved on a gram scale, based on an aza-6π electrocyclization-aromatization strategy for construction of the tetra-substituted pyridine ring. A bicyclic intermediate was expeditiously prepared by using [2+2] photocycloaddition and chemoselective Baeyer-Villiger oxidation, which was further elaborated to a densely substituted aza-triene. An electrocyclization-aromatization cascade was utilized to forge the tetracyclic core of this natural product, and the side chain was introduced through diastereoselective acylation and reduction.

Scalable Total Synthesis of Acremolactone B

AbstractAcremolactone B is a pyridine‐containing azaphilone‐type polyketide. The first total synthesis of this molecule was achieved on a gram scale, based on an aza‐6π electrocyclization–aromatization strategy for construction of the tetra‐substituted pyridine ring. A bicyclic intermediate was expeditiously prepared by using [2+2] photocycloaddition and chemoselective Baeyer–Villiger oxidation, which was further elaborated to a densely substituted aza‐triene. An electrocyclization–aromatization cascade was utilized to forge the tetracyclic core of this natural product, and the side chain was introduced through diastereoselective acylation and reduction.

Enantiomeric purity determination of lactofen formulations through Chemometric Deconvolution of partially overlapped chromatographic profiles

Lactofen is a chiral restricted-use herbicide, classified as toxicity class I by the Environmental Protection Agency (EPA), commonly used to control broadleaved weeds. While the observed herbicidal activity mostly derives from the (S)-(+)-enantiomer, formulations have been manufactured as a mixture of both enantiomers. In this work, we present a quantitative method for the enantiomeric determination of lactofen in commercial formulations based on the development of a second-order calibration to assist the selectivity of chiral separation under reversed-phase liquid chromatographic mode coupled to diode array detection. Chromatographic conditions were aimed to minimize analysis time and solvent consumption. This approach is feasible because second-order calibration allows for the quantification of overlapping bands and analytes in the presence of interferences. Chromatographic-spectral matrices were processed by unfolded partial least-squares coupled to residual bilinearization. The proposed methodology was evaluated through validation samples, achieving relative errors of predictions of 2–4 %. Finally, commercial formulations were subjected to minimal sample treatment and analyzed, and figures of merit for real samples were determined. The described methodology results suitable for the determination of enantiomeric purity and quality control in commercial lactofen formulations.

Tautomerism of herbicides metribuzin, diclosulam and clethodim: evaluation of different parameters for structure assignation

Pesticides are widely used in agriculture, and they can cause serious damage to human health and to the environment. In this work, three herbicides are studied regarding possible tautomeric equilibria: clethodim, diclosulam and metribuzin. Tautomerism is a key reaction that is directly related to action, disposition and toxicity of herbicides, and here lies the importance of this study. The specific aim of this work is to compare classical parameters (MAE and R2) with DP4+ method as a tool for obtaining relevant information about tautomeric equilibria in the three compounds, contrasting experimental NMR data with theoretical calculations carried out using DFT methods.1H and 13C NMR spectra of the three herbicides were recorded in DMSO‑d6. Additionally, HSQC and COSY spectra were obtained for clethodim. Theoretical calculations were carried out in order to obtain optimized geometries in vacuum (using B3LYP method at 6–31G(d,p) level of theory); and chemical shifts of nuclei corresponding to all possible tautomers of each herbicide were obtained by means of B3LYP-GIAO method using 6–311+G(2d,p) basis set.In the three cases, classical comparison parameters MAE and R2 fail in the assignation of tautomers since they gave doubtful or even inconsistent results. In the case of metribuzin, MAE values obtained from 1H and 13C point towards different structures. R2 and MAE values obtained from 1H and 13C are very close when comparing the two tautomers, and the assignation is not certain. The case of clethodim is more confusing, since the R2 and MAE values suggest that all signals correspond to the same structure. DP4+ method, on the other hand, gave more reliable results (within the set of proposed structures). It is important to remark that DP4+ method has been used before for tautomer assignation in only one case (to the best of our knowledge), and it has also proven successful in this context of use.We concluded that metribuzin and diclosulam exist in solution in one major tautomeric form (aminotriazinone and sulfonamide, respectively), while two tautomers of similar energy (E- and Z-ketoenolimine complexed with DMSO) are proposed for clethodim.

Two Cytochrome P450s, CYP709B1 and CYP704C1, Play Essential Roles in Metabolism-Based Multiple Herbicide Resistance in American Sloughgrass (Beckmannia syzigachne (Steud.) Fernald).

This study confirmed a field population of American sloughgrass (Beckmannia syzigachne (Steud.) Fernald) that developed simultaneously high levels of resistance (resistance index >10) to three divergent modes of action herbicides: fenoxaprop-P-ethyl, mesosulfuron-methyl, and isoproturon. The resistance phenotype observed in this population was not attributed to target-site alterations; rather, the resistant plants exhibited a significant increase in the activity of cytochrome P450s (P450s) and enhanced metabolism rates for all three herbicides. RNA sequencing revealed significant upregulation of two P450s, CYP709B1 and CYP704C1, in the resistant plants both before and after herbicide treatments. Molecular docking predicted that the homology models of these P450s should exhibit a binding affinity for a range of herbicides. The heterologous expression of the identified P450s in yeast cells indicated improved growth in the presence of all three of the aforementioned herbicides. Collectively, the increased expression of CYP709B1 and CYP704C1 likely contributed to the P450s-mediated enhanced metabolism, thereby conferring multiple herbicide resistance in B. syzigachne.

Allelopathic Potential of Volatile Oils from Mentha piperita and Chrysanthemum coronarium Growing in Western Algeria

Background: The allelopathic effects of the essential oils of M. piperita and C. coronarium on seed germination of two wheat species qualify them as bio-herbicides. Objective: In order to search for natural plant-based products that may have herbicidal action, we selected two plant species, M. piperita and C. coronarium, to evaluate the allelopathic potential of their essential oils on wheat seed germination of two wheat species. Methods: Aerials parts of M. piperita and C. Coronarium were subjected to hydrodistillation using a Clevenger-type apparatus to extract essential oils, followed by characterization using gas chromatography coupled with mass spectrometry. Bioassays were conducted with ethanol as the organic solvent, employing three concentrations (0.25, 0.5, and 0.75 μl/ml of oil/ethanol) to assess their effects on the seed and seedling growth of two wheat species. Results: Under laboratory conditions, extracts of Mentha piperita and Chrysanthemum coronarium oils at varying concentrations (0.25 μl, 0.5 μl, and 0.75 μl) were examined for their effects on two wheat species (Triticum durum L. and Triticum aestivum L.). The yields of the obtained oils were 1.19% and 0.25%, respectively. The chemical composition of the essential oils extracted from M. piperita and C. coronarium was dominated by oxygenated monoterpenes, representing 97.5% and 94.9%, respectively. The tested essential oils strongly inhibit seed germination and seedling growth (root length LR and shoot length LPA) of both wheat species studied. The inhibition increased as the oil concentration increased, although this increase differed between the two species. This study has shown that the tested essential oils possess an interesting inhibitory allelopathic potential. Conclusion: The findings of this study indicate that the tested essential oils possess promising allelopathic properties, suggesting them as natural bio-herbicides.

Varietal Tolerance of Cucurbitaceous Crops with S-metolachlor Applied Postemergence

Cucurbit crops comprise ∼25% of the vegetable acreage in the mid-Atlantic and Northeastern United States. However, options for postemergence weed control in these crops are limited. Overlapping herbicides is a technique that involves sequential applications of soil-applied residual herbicides to lengthen herbicidal activity before the first herbicide dissipates. Residual herbicides such as S-metolachlor will not control emerged weeds, but weed control efficacy may be extended if these herbicides are applied after crop emergence, but before weed emergence occurs. Currently S-metolachlor is not labeled for broadcast applications over cucurbit crops. Greenhouse studies were conducted to evaluate pumpkin, cucumber, and summer squash variety response to varying S-metolachlor rates. S-metolachlor was applied at 1.42 and 2.85 lb/acre at the two-leaf stage of pumpkin and 0.71, 1.42, 2.85, and 5.7 lb/acre at the two-leaf stage of cucumber and summer squash. Cucumber showed a greater response to S-metolachlor with up to 67% injury observed at 5.70 lb/acre. S-metolachlor applications to pumpkin and summer squash resulted in less than 6% injury, regardless of application rate or crop variety. S-metolachlor applied at 2.85 lb/acre reduced pumpkin and cucumber dry weight 6% and 19%, respectively, but did not reduce squash dry weight. S-metolachlor reduced cucumber dry weight 78% for all varieties. Pumpkin varieties ‘Munchkin’ and ‘Baby Bear’ exhibited a 23% difference in dry weight, but no other differences were observed among other varieties because of S-metolachlor applications. Summer squash varieties ‘Respect’ and ‘Golden Glory’ exhibited a 31% difference in dry weight, but no other differences were observed among other varieties. Results show that pumpkin and summer squash demonstrated good crop safety when S-metolachlor was applied as a broadcast treatment after crop emergence. However, caution should be urged when applying this herbicide to cucumber.

English

The use of allelopathic bacteria to combat weed infestation in crops is regarded as an effective technology for sustainable agriculture and environment. In this regard, six bacterial strains from the genus Pseudomonas were selected for their ability to inhibit the germination and growth of Leptochloa chinensis (L.) and Dactyloctenium aegyptium (L.) while promoting the growth of rice. These strains were applied to the target weeds and rice using different application methods viz. seed priming, liquid application, and foliar application. The results showed that all strains possessed herbicidal activity and significantly reduced growth of L. chinensis. Shoot length, root length, and fresh biomass of D. aegyptium were also significantly reduced in all strains by 60, 55, and 76%, respectively, with the exception of R15-4. Additionally, the growth suppression of both weed species was more prominent in the liquid application. The selected allelopathic strains also demonstrated plant growth-promoting traits and improved the growth and physiological parameters of rice in all three application methods, with the best results achieved with liquid and foliar applications. The survival efficiency of the bacterial strains was also tested using four different carrier materials, where the press mud was found the best carrier for controlling L. chinensis and D. aegyptium.

Discovery of novel Propionamide-Pyrazole-Carboxylates as Transketolase-inhibiting herbicidal candidates.

Transketolase (TKL, EC 2.2.1.1) is a key enzyme in the pentose phosphate pathway and Calvin cycle, and is expected to act as a herbicidal site-of-action. On the basis of TKL, we designed and synthesized a series of 1-oxy-propionamide-pyrazole-3-carboxylate analogues and evaluated their herbicidal activities. Methyl 1-methyl-5-((1-oxo-1-((4-(trifluoromethyl)phenyl)amino)propan-2-yl)oxy)-1H-pyrazole-3-carboxylate (C23) and methyl 1-methyl-5-((1-oxo-1-((perfluorophenyl)amino)propan-2-yl)oxy)-1H-pyrazole-3-carboxylate (C33) were found to provide better growth-inhibition activities against Digitaria sanguinalis root than those of nicosulfuron, mesotrione and pretilachlor at 200 mg L-1 using the small-cup method. These compounds were also identified as promising compounds in pre-emergence and postemergence herbicidal-activity experiments, with relatively good inhibitory effects toward Amaranthus retroflexus and D. sanguinalis at 150 g ai ha-1. In addition, enzyme inhibition assays and molecular docking studies revealed that C23 and C33 interact favourably with SvTKL (Setaria viridis TKL). C23 and C33 are promising lead TKL inhibitors for the optimization of new herbicides. © 2024 Society of Chemical Industry.

Discovery of Novel N-Phenyltriazinone Derivatives Containing Oxime Ether or Oxime Ester Moieties as Promising Protoporphyrinogen IX Oxidase Inhibitors.

Protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) is one of the most important targets for the discovery of green herbicides. In order to find novel PPO inhibitors with a higher herbicidal activity, a series of novel N-phenyltriazinone derivatives containing oxime ether and oxime ester groups were designed and synthesized based on the strategy of pharmacophore and scaffold hopping. Bioassay results revealed that some compounds showed herbicidal activities; especially, compound B16 exhibited broad-spectrum and excellent 100% herbicidal effects to Echinochloa crusgalli, Digitaria sanguinalis, Setaria faberii, Abutilon juncea, Amaranthus retroflexus, and Portulaca oleracea at a concentration of 37.5 g a.i./ha, which were comparable to trifludimoxazin. Nicotiana tabacum PPO (NtPPO) enzyme inhibitory assay indicated that B16 showed an excellent enzyme inhibitory activity with a value of 32.14 nM, which was similar to that of trifludimoxazin (31.33 nM). Meanwhile, compound B16 revealed more safety for crops (rice, maize, wheat, peanut, soybean, and cotton) than trifludimoxazin at a dose of 150 g a.i./ha. Moreover, molecular docking and molecular dynamics simulation further showed that B16 has a very strong and stable binding to NtPPO. It indicated that B16 can be used as a potential PPO inhibitor and herbicide candidate for application in the field.

Oxime chemistry in crop protection.

An overview is given on the significance of the oxime moiety in crop protection chemistry. This review focuses on the two most important aspects of agrochemical oximes, which are the occurrence and role of oxime groups in compounds with herbicidal, fungicidal and insecticidal activity, as well as the application of oxime derivatives as intermediates in the synthesis of crop protection agents not bearing any oxime function. Especially noteworthy is the fact, that in the synthesis of agrochemicals, oximes can be cyclized to isooxazoline, isoxazole, oxadiazole, oxazine, pyrrole, isothiazole and imidazole rings. © 2024 Society of Chemical Industry.

Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals.

Scaffold structures, new mechanisms of action, and targets present enormous challenges in the discovery of novel pesticides. The discovery of new scaffolds is the basis for the continuous development of modern agrochemicals. Identification of a good scaffold such as triazole, carbamate, methoxy acrylate, pyrazolamide, pyrido-pyrimidinone mesoionic, and bisamide often leads to the development of a new series of pesticides. In addition, pesticides with the same target, including the inhibitors of succinate dehydrogenase (SDH), oxysterol-binding-protein, and p-hydroxyphenyl pyruvate dioxygenase (HPPD), may have the same or similar scaffold structure. Recent years have witnessed significant progress in the discovery of new pesticides using natural products as scaffolds or bridges. In recent years, there have been increasing reports on the application of natural benzopyran compounds in the discovery of new pesticides, especially osthole and coumarin. A systematic and comprehensive review of benzopyran active compounds in the discovery of new agricultural chemicals is helpful to promote the discussion and development of benzopyran active compounds. Therefore, this work systematically reviewed the research and application of benzopyran derivatives in the discovery of agricultural chemicals, summarized the antiviral, herbicidal, antibacterial, fungicidal, insecticidal, nematicidal and acaricidal activities of benzopyran active compounds, and discussed the structural-activity relationship and mechanism of action. In addition, some active fragments were recommended to further optimize the chemical structure of benzopyran active compounds based on reference information.

Discovery of Novel Pyridazine Herbicides Targeting Phytoene Desaturase with Scaffold Hopping.

Phytoene desaturase (PDS) is a critical functional enzyme in blocking ζ-carotene biosynthesis and is one of the bleaching herbicide targets. At present, norflurazon (NRF) is the only commercial pyridazine herbicide targeting PDS. Therefore, developing new and diverse pyridazine herbicides targeting PDS is urgently required. In this study, diflufenican (BF) was used as the lead compound, and a scaffold-hopping strategy was employed to design and synthesize some pyridazine derivatives based on the action mode of BF and PDS. The preemergence herbicidal activity tests revealed that compound 6-chloro-N-(2,4-difluorophenyl)-3-(3-(trifluoromethyl)phenoxy)pyridazine-4-carboxamide (B1) with 2,4-diF substitution in the benzeneamino ring showed 100% inhibition rates against the roots and stems of Echinochloa crus-galli and Portulaca oleracea at 100 μg/mL, superior to the inhibition rates of BF. Meanwhile, compound B1 demonstrated excellent postemergence herbicidal activity against broadleaf weeds, which was similar to that of BF (inhibition rate of 100%) but superior to that of NRF. This indicated that 6-Cl in the pyridazine ring is the key group for postemergence herbicidal activity. In addition, compound B1 could induce downregulation of PDS gene expression, 15-cis-phytoene accumulation, and Y(II) deficiency and prevent photosynthesis. Therefore, B1 can be considered as a promising candidate for developing high-efficiency PDS inhibitors.

Discovery of a New Class of Lipophilic Pyrimidine-Biphenyl Herbicides Using an Integrated Experimental-Computational Approach.

Herbicides are useful tools for managing weeds and promoting food production and sustainable agriculture. In this study, we report on the development of a novel class of lipophilic pyrimidine-biphenyl (PMB) herbicides. Firstly, three PMBs, Ia, IIa, and IIIa, were rationally designed via a scaffold hopping strategy and were determined to inhibit acetohydroxyacid synthase (AHAS). Computational simulation was carried out to investigate the molecular basis for the efficiency of PMBs against AHAS. With a rational binding mode, and the highest in vitro as well as in vivo potency, Ia was identified as a preferable hit. Furthermore, these integrated analyses guided the design of eighteen new PMBs, which were synthesized via a one-step Suzuki-Miyaura cross-coupling reaction. These new PMBs, Iba-ic, were more effective in post-emergence control of grass weeds compared with Ia. Interestingly, six of the PMBs displayed 98-100% inhibition in the control of grass weeds at 750 g ai/ha. Remarkably, Ica exhibited ≥ 80% control against grass weeds at 187.5 g ai/ha. Overall, our comprehensive and systematic investigation revealed that a structurally distinct class of lipophilic PMB herbicides, which pair excellent herbicidal activities with new interactions with AHAS, represent a noteworthy development in the pursuit of sustainable weed control solutions.

Known and potential benefits of applying herbicides with glutathione S-transferase inhibitors and inducers – a review

Abstract Weed resistance to herbicides has increased exponentially during the past 30 to 40 years, consequently reducing the number of effective products available to control certain species and populations. Future efforts should target not only the discovery of new protein binding sites and the development of new molecules, but also the revival of old molecules with reduced efficacy due to widespread herbicide resistance. The addition of herbicide synergists that inhibit metabolic pathways or enhance intrinsic plant stress is a possible solution to ameliorate the negative effects caused by the lack of new herbicide chemistries. Glutathione S-transferase (GST) enzymes are involved with numerous herbicide detoxification reactions and plant stress responses. This review approaches the potential use of natural and synthetic GST-inhibitors to enhance herbicidal activity or induce crop safety to provide effective, sustainable weed management strategies in the future.

Synthesis, Characterization and Evaluation of the Antimicrobial and Herbicidal Activities of Some Transition Metal Ions Complexes with the Tranexamic Acid.

New tranexamic acid (TXA) complexes of ferric(III), cobalt(II), nickel(II), copper(II) and zirconium(IV) were synthesized and characterized by elemental analysis (CHN), conductimetric (Λ), magnetic susceptibility investigations (μeff), Fourier transform infrared (FT-IR), proton nuclear magnetic resonance (1H-NMR), ultraviolet visible (UV-vis.), optical band gap energy (Eg) and thermal studies (TG/DTG and DTA). TXA complexes were established in 1 : 2 (metal: ligand) stoichiometric ratio according to CHN data. Based on FT-IR and 1H-NMR data the disappeared of the carboxylic proton supported the deprotonating of TXA and linked to metal ions via the carboxylate group's oxygen atom as a bidentate ligand. UV-visible spectra and magnetic moment demonstrated that all chelates have geometric octahedral structures. Eg values indicated that our complexes are more electro conductive. DTA revealed presence of water molecules in inner and outer spheres of the complexes. DTA results showed that endothermic and exothermic peaks were identified in the degradation mechanisms. The ligand and metal complexes were investigated for their antimicrobial and herbicidal efficacy. The Co(II) and Ni(II) complexes showed antimicrobial activity against some tested species. The obtained results showed a promising herbicidal effect of TXA ligand and its metal complexes particularly copper and zirconium against the three tested plants.

Endothall and 2,4-D Activity in Milfoil Hybrid (Myriophyllum spicatum × M. sibiricum) when Applied Alone and in Combination

Abstract Eurasian watermilfoil (Myriophyllum spicatum L.) is an invasive aquatic plant that can hybridize with the native Northern watermilfoil (Myriophyllum sibiricum Kom.). These milfoil hybrids (M. spicatum × M. sibiricum) are becoming more prevalent in many lakes where the invasive and the native milfoil co-occur. Hybrid plants are more vigorous than either parent with a faster growth rate and lower sensitivity to some herbicides. The aquatic herbicides, endothall and 2,4-D, provide two effective modes of action (MOA) for management of the hybrids. For more than a decade, these two herbicides have been used in combination as an effective control option and a resistance management strategy. How this combination impacts herbicide movement and efficacy is unknown. Therefore, the objective of this research was to determine the activity of endothall and 2,4-D combined compared to activity applied alone. Absorption and translocation of endothall, 2,4-D and the combination was determined in hybrid plants over a 96-h time course. Endothall bioaccumulation was not impacted when these herbicides were applied in combination; however, 2,4-D accumulation increased by 80%, relative to when 2,4-D was applied alone. Endothall translocation from shoots to roots decreased by almost 50% when applied in combination with 2,4-D (alone = 16.7% ± 2.6; combination = 9.2% ± 1.2). Shoot-to-root translocation of 2,4-D also decreased when the two herbicides were applied in combination (24.8% ± 2.6 when applied alone to only 3.93% ± 0.4 when in the presence of endothall). This research demonstrates that combining herbicides can significantly impact herbicide activity in plants. Future research is needed to determine if this reduced translocation negatively impacts operational effectiveness when these herbicides applied in combination.

Design, Synthesis, and Biological Activity of Novel Triketone-Containing Phenoxy Nicotinyl Inhibitors of HPPD.

4-Hydroxyphenylpyruvate dioxygenase (HPPD) is a crucial target enzyme in albino herbicides. The inhibition of HPPD activity interferes with the synthesis of carotenoids, blocking photosynthesis and resulting in bleaching and necrosis. To develop herbicides with excellent activity, a series of 3-hydroxy-2-(6-substituted phenoxynicotinoyl)-2-cyclohexen-1-one derivatives were designed via active substructure combination. The title compounds were characterized via infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopies, and high-resolution mass spectrometry. The structure of compound III-17 was confirmed via single-crystal X-ray diffraction. Preliminary tests demonstrated that some compounds had good herbicidal activity. Crop safety tests revealed that compound III-29 was safer than the commercial herbicide mesotrione in wheat and peanuts. Moreover, the compound exhibited the highest inhibitory activity against Arabidopsis thaliana HPPD (AtHPPD), with a half-maximal inhibitory concentration of 0.19 μM, demonstrating superior activity compared with mesotrione (0.28 μM) in vitro. A three-dimensional quantitative structure-activity relationship study revealed that the introduction of smaller groups to the 5-position of cyclohexanedione and negative charges to the 3-position of the benzene ring enhanced the herbicidal activity. A molecular structure comparison demonstrated that compound III-29 was beneficial to plant absorption and conduction. Molecular docking and molecular dynamics simulations further verified the stability of the complex formed by compound III-29 and AtHPPD. Thus, this study may provide insights into the development of green and efficient herbicides.

Novel Uracilphenyl sulfonamide-based inhibitors of protoporphyrinogen oxidase: Design, synthesis, and herbicidal activity

Herein, we aimed to develop effective herbicidal compounds by synthesizing 26 novel uracil derivatives containing sulfonamide groups based on the active group splicing principle, with saflufenacil as the reference compound. The structures of the final products were confirmed through 1H NMR, 13C NMR, and HRMS analyses. According to the results, 21 and 19 compounds exhibited outstanding (80 %-100 %) and 60–100 % control efficacies against broadleaf weeds (Zinnia elegans and Abutilon theophrasti) at concentrations of 150 g/hm2 and 37.5 g/hm2, respectively. Notably, compound 2a demonstrated 100 % control efficacy against Zinnia elegans even at the lowest tested concentration of 9.375 g/hm2. On the other hand, the examined compounds exhibited minimal efficacy against other grass weeds, such as Setaria glauca and Echinochloa crusgalli. Furthermore, molecular docking analysis revealed that compound 2a formed hydrogen bonds with Protoporphyrinogen Oxidase (PPO).Studies of the electrostatic potential analysis of the molecular surface showed that the highly active compounds 2a and saflufenacil have similar charge distributions, which may play an important role in the docking of the compounds with their target receptors.These findings offer valuable insights and guidance for developing more effective herbicides, paving the way for future advances in weed control tactics.