Search Results (30)

Triazolopyrimidine sulfonamide herbicides, a prominent class of acetohydroxyacid synthase (AHAS) inhibitors, are exceptionally effective in controlling weeds in agricultural settings. To overcome metabolic resistance caused by the 5-demethylation of pyroxsulam, we sought to replace its 5-methoxy group on the triazolopyrimidine ring with alkyl substituents. This led to the synthesis of a series of N-(7-oxo-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)arylsulfon-amides, which displayed significant structural diversification potential, culminating in the identification of the herbicidal hit compound I-20. However, the suboptimal lipophilicity compromised its herbicidal efficacy. To rectify this limitation, we modified the 7-carbonyl group to a tert-butoxy group, resulting in the highly active compound I-29. This compound demonstrated herbicidal activity comparable to or exceeding that of penoxsulam against various tested weeds, establishing it as a promising new lead compound and a candidate herbicide for further investigation. Subsequent studies revealed that I-29 exhibited a receptor binding mode and herbicidal activity profiles that closely aligned with those of penoxsulam. Moreover, its spatial structure was found to be even more conducive to inhibiting flavin adenine dinucleotide (FAD)-mediated AHAS activity. This research not only sheds light on addressing the challenge of 5-demethylation metabolic resistance in triazolopyrimidine sulfonamide herbicides but also offers new avenues for the development of AHAS-inhibiting triazolopyrimidine sulfonamide herbicides. Full article

Florpyrauxifen-benzyl (FPB) is an auxin-mimic herbicide that controls selected grasses, sedges, and broadleaves in rice cropping systems. Field experiments were conducted in 2023 and 2024 to characterize the effects of FPB on crop safety and weed control when applied alone or in combination with other herbicides, and to assess whether FPB can provide season-long, effective weed management. Base treatments of benzobicyclon (BBC)/halosulfuron-methyl (HSM), clomazone (CLM), or thiobencarb (TBC) were applied on the day of seeding (DOS) or within the 2-leaf stage (LS) rice and followed by foliar treatments of FPB alone or in a mixture with bispyribac-sodium (BPS), penoxsulam (PNX)/cyhalofop-butyl (CHB), or propanil (PPL). Additionally, FPB was applied alone with no prior base treatment, in combination with a mixture partner, and as a sequential treatment, 14 days apart, with the first application made to 4- to 5-LS rice; in contrast, the second application was made to mid-tillering rice. The FPB applied alone or in sequential application showed results for more than 98% of watergrasses and 100% of ricefield bulrush, smallflower umbrella sedge, ducksalad, redstems, and all other broadleaves control at 56 days after treatment (DAT). When applied after the base treatments, the weed control increased to 100% for all weed species at 14 DAT. The sequential application of FPB achieved the highest yields of 7683 kg ha⁻¹ in 2023 and 11,249 kg ha⁻¹ in 2024, resulting in 3.6- and 6.4-fold increases in rice yield over the nontreated control. Owing to its excellent sedge and broadleaf weed control and good activity on troublesome grasses, such as barnyardgrass, FPB could be an essential part of the weed management programs in rice production systems. Full article

The specific objectives include three points: (1) to clarify the dynamic change laws of the contents of three key endogenous hormones, namely, indole-3-acetic acid (IAA), gibberellin (GA), and abscisic acid (ABA), in foxtail millet leaves after penoxsulam treatment, and their correlations with drug dose and treatment time; (2) to analyze the effects of different doses of penoxsulam on the antioxidant system of foxtail millet, specifically including the change characteristics of hydrogen peroxide (H₂O₂), superoxide anion (O₂⁻), reduced glutathione (GSH) content, and cell membrane permeability (MP); and (3) to reveal the correlation between endogenous hormone changes and antioxidant system indicators through correlation analysis so as to provide a direct experimental basis for the screening of safe doses of penoxsulam application in foxtail millet fields and the research on the herbicide stress resistance mechanism of foxtail millet. Using Jingu 21 as the test material, four penoxsulam dose levels were set through pot and field experiments. The changes in endogenous hormone content, antioxidant system indexes, and phenotypic indicators of foxtail millet were determined at different periods after treatment, and the correlation between endogenous hormones and antioxidant systems was analyzed. Compared with the control (P₀), the contents of IAA and GA in foxtail millet showed a “first increasing and then decreasing” trend, while the content of ABA showed a continuous increasing trend. With the increase in penoxsulam concentration, the contents of H₂O₂, O₂⁻, GSH, and MP in foxtail millet gradually increased. A correlation analysis showed that there was a significant correlation between leaf endogenous hormones and the defense capacity of the antioxidant system. After penoxsulam treatment, foxtail millet leaves showed dynamic changes of “first increasing and then decreasing” in IAA and GA contents, and a continuous increase in ABA contents. At the same time, H₂O₂, O₂⁻, GSH content, and MP increased significantly with the increase in the drug dose. It is speculated that foxtail millet may indirectly regulate the defense ability of the antioxidant system by regulating the content of endogenous hormones to alleviate the damage of herbicide stress. Full article

Foxtail millet is a characteristic miscellaneous grain crop with many benefits in current agricultural production and is crucial in the adjustment of the planting structure and the sustainable development of dry farming. However, the harmful effects of weeds have become a critical challenge, restricting the modern production of foxtail millet. The effect of penoxsulam on the chlorophyll metabolism pathway of foxtail millet and its physiological mechanism was studied. Spraying penoxsulam on foxtail millet leaves significantly reduced the content of chlorophyll synthesis precursors (5-aminolevulinic acid (ALA), Porphobilinogen (PBG), Protoporphyrin IX (ProtoIX), Mg-protoporphyrin IX (Mg-ProtoIX), and Protochlorophyllide (Pchlide)). Moreover, the activities of key synthetic enzymes (magnesium chelatase (MgCh) decreased compared to control, while the activities of degrading enzymes (pheophorbide a oxygenase (PAO) and pheophytinase activities (PPH) increased significantly. The study revealed the mechanism of penoxsulam inducing crop phytotoxicity by interfering with the dynamic balance of chlorophyll metabolism, which provided a theoretical basis for the scientific application of herbicides and the study of foxtail millet drug resistance. Full article

Fenoxaprop-P-ethyl (FE) can effectively control weeds in rice fields, but it has been found to cause phytotoxicity in rice. In this study, the phytotoxicity of FE was mitigated by perilla leaf essential oil (PEO) in rice seedlings. The injury recovery rates (IRRs) for shoot length and fresh weight treated with 800 mg/L of PEO were 101.51% and 99.05%, respectively. Moreover, the damage of s-metolachlor and pretilachlor was also alleviated when co-applied with 800 mg/L PEO; the IRR of s-metolachlor phytotoxicity was 26.07% and 27.34%, respectively, and the IRR of pretilachlor phytotoxicity was 127.27% and 124.39%, respectively. However, PEO had no significant effect on the phytotoxicity of pinoxaden, mesotrione, penoxsulam, mesosulfuron-methyl, and nicosulfuron. The results of GC–MS analysis showed that a total of 23 components were detected in PEO, among which linalool (36.49%), linalyl formate (26.96%), α-terpineol (10.63%), 2-hexanoylfuran (5.81%), geranyl acetate (4.13%), and neryl acetate (2.30%) were the primary components. Among them, 2-hexanoylfuran was the most effective component to alleviate FE damage, for which the IRR of shoot length and fresh weight was 73.17% and 73.02%, respectively, followed by the geranyl acetate, for which the IRR was 72.32% and 60.56%, respectively, and neryl acetate, for which the IRR was 65.28% and 58.11%, respectively. Furthermore, the application of 50 mg/L of 2-hexanofuran significantly improved the tolerance of shoot length and fresh weight to FE stress by factors of 5.32 and 5.35, respectively. This research demonstrates that PEO and 2-hexanoylfuran have the potential to serve as natural safeners to reduce phytotoxicity. Full article

Grass damage has become an important factor restricting foxtail millet production; chemical weeding can help resolve this issue. However, special herbicides in foxtail millet fields are lacking. Penoxsulam has a broad weed control spectrum and a good control effect. In this project, Jingu 21 was used as the test material, and five different concentrations of penoxsulam were used for spraying test in the three–five leaf stage. In this experiment, the effects on the growth of foxtail millet were discussed by measuring the agronomic characters and antioxidant capacity of foxtail millet after spraying penoxsulam. The results showed that: (1) penoxsulam is particularly effective in controlling Amaranthus retroflexus L. (A. retroflexus) and Echinochloa crus-galli (L.) Beauv. (E. crus-galli), but is ineffective in controlling Chenopodium album L. (C. album) and Digitaria sanguinalis (L.) Scop. (D. sanguinalis); (2) the stem diameter, fresh weight, and dry weight of the above-ground parts decreased with the increase in spraying amount; (3) as the spraying dosage increased, the superoxide (SOD), peroxidase (POD), and catalase (CAT) activities in the foxtail millet initially increased and subsequently decreased; the malonaldehyde (MDA) content increased. Our experiment found that 1/2X and 1X spraying dosages had certain application value in controlling gramineous weeds in foxtail millet field. Other spraying dosages are not recommended as they may harm the crops. Our findings provide reference for identifying new herbicides in the foxtail millet field. Full article

In this study, we aimed to identify suitable herbicides for quinoa fields in Anhui Province and explore the value of their potential application in order to achieve the sustainable weed management of the crop and tackle the global issue of unregistered herbicides in quinoa fields. Employing a pre-emergence seed soaking method, we evaluated the effects of different herbicides, such as anilofos, prometryn, pendimethalin, and atrazine on the germination inhibition rate of quinoa seeds, as well as their impacts on the growth indicators of quinoa seedlings. Our findings show that, while these herbicides initially suppressed quinoa seed germination, this effect decreased over time, allowing for the successful germination of all seeds, suggesting the existence of a recovery mechanism in quinoa. An increase in herbicide concentration was correlated with significant decreases in the germination vigor and index of quinoa seeds, along with a decrease in plant height, root length, and fresh weight. Notably, anilofos, prometryn, pendimethalin, and atrazine demonstrated significant inhibitory effects on quinoa seedlings, thus providing critical insights into the sensitivity of quinoa to these chemicals. Greenhouse pot experiments showed that pre-emergence herbicides, such as napropamide, pretilachlor, s-metolachlor, and anilofos, and post-emergence herbicides, including fluroxypyr, penoxsulam, clethodim, quizalofop-P-ethyl, oxaziclomefone, metamifop, benzobicyclon, nicosulfuron, and pinoxaden, are safe for quinoa and suitable for further field trials, broadening the options for integrated weed management strategies. The results of the mixture experiments indicated that penoxsulam and metamifop are safe for quinoa at a ratio of 1:4.6, and their combined activities against dominant weeds in quinoa fields in Anhui Province, such as Digitaria sanguinalis, Cyperus iria, and Amaranthus viridis, were higher than those of single-agent doses, with fresh weight inhibition rates ranging from 66.98% to 92.16% and selectivity indexes ranging from 176.88 to 3282.17. Therefore, this mixture offers a promising approach to enhanced weed control in a sustainable manner. Full article

Aquatic ecosystems can suffer inadvertent contamination from widely used herbicides. This study delves into the relative toxicity of 36 herbicides on green algae, exploring 11 distinct modes of action and 25 chemical structure classes. Through a 72-h algal growth inhibition test, it was found that herbicides targeting acetolactate synthase (ALS), photosystem II (PSII inhibitors), microtubule assembly, very-long-chain fatty acid (VLCFA) synthesis, and lipid synthesis exhibited high toxicity, with 72-h EC50 (half-maximal effective concentration) values ranging from 0.003 mg/L to 24.6 mg/L. Other pesticide types showed moderate to low toxicity, with EC50 values ranging from 0.59 mg/L to 143 mg/L. Interestingly, herbicides sharing the same mode of action but differing in chemical composition displayed significantly varied toxicity. For instance, penoxsulam and pyribenzoxim, both ALS inhibitors, demonstrated distinct toxicity levels. Similarly, terbuthylazine and bentazone, both PSII inhibitors, also exhibited differing toxicities. Notably, herbicides approved for rice cultivation showed lower toxicity to green algae compared to those intended for terrestrial plants. These data offer valuable insights for assessing the potential risks posed by these chemicals to aquatic organisms. Additionally, to prevent or minimize herbicide residual effects, modern management practices were reviewed to offer practical guidance. Full article

Foxtail millet planting has a long history and profound role in agricultural civilization. However, weeds have become one of the obstacles restricting the development of the foxtail millet industry. Penoxsulam, as an early post-emergence herbicide for controlling gramineous weeds in paddy fields, is effective for some broadleaf weeds. In this study, six different doses (CK, 0.5X, 1X, 2X, 3X, 4X) of penoxsulam were sprayed at the 3–5 leaf stage of the conventional variety Jingu 21 to study its effect on the growth and development of foxtail millet, in order to screen out the appropriate spraying concentration. The main results are as follows: Within 15 days after spraying penoxsulam, the plant height and leaf area of foxtail millet decreased with the increase in spraying dose, and gradually recovered 15–25 days after spraying, but there were still significant differences compared with CK. The photosynthetic pigment content, net photosynthetic rate (Pn), transpiration rate (Tr), stomatal conductance (Gs), the maximum photochemical efficiency (Fv/Fm), photosynthetic system II actual photochemical efficiency (Y(II)), and photochemical quenching coefficient (qP) of foxtail millet decreased with an increase in the penoxsulam spraying dose, while the intercellular CO₂ concentration (Ci) and non-photochemical quenching coefficient (NPQ) showed an upward trend. There was almost no significant difference in each index between the spraying dose of 0.5X and 1X and CK, but the photosynthesis of foxtail millet leaves was still significantly inhibited under a spraying dose of 3X and 4X. Penoxsulam had certain growth-inhibiting effects on Echinochloa crus-galli (L.) Beauv. (E. crus-galli), Digitaria sanguinalis (L.) Scop. (D. sanguinalis), Chenopodium album L. (C. album), and Amaranthus retroflexus L. (A. retroflexus) which increased as the spraying dosage increased. Our study found that spraying dose groups of 0.5X and 1X penoxsulam were safe for foxtail millet growth and could be used to control gramineous weeds in fields. Other spraying doses are not recommended in the field due to their serious phytotoxicity to foxtail millet, which provides a new measure for weed control in foxtail millet fields. Full article

A spectral image analysis has the potential to replace traditional approaches for assessing plant responses to different types of stresses, including herbicides, through non-destructive and high-throughput screening (HTS). Therefore, this study was conducted to develop a rapid bioassay method using a multi-well plate and spectral image analysis for the diagnosis of herbicide activity and modes of action. Crabgrass (Digitaria ciliaris), as a model weed, was cultivated in multi-well plates and subsequently treated with six herbicides (paraquat, tiafenacil, penoxsulam, isoxaflutole, glufosinate, and glyphosate) with different modes of action when the crabgrass reached the 1-leaf stage, using only a quarter of the recommended dose. To detect the plant’s response to herbicides, plant spectral images were acquired after herbicide treatment using RGB, infrared (IR) thermal, and chlorophyll fluorescence (CF) sensors and analyzed for diagnosing herbicide efficacy and modes of action. A principal component analysis (PCA), using all spectral data, successfully distinguished herbicides and clustered depending on their modes of action. The performed experiments showed that the multi-well plate assay combined with a spectral image analysis can be successfully applied for herbicide bioassays. In addition, the use of spectral image sensors, especially CF images, would facilitate HTS by enabling the rapid observation of herbicide responses at as early as 3 h after herbicide treatment. Full article

Penoxsulam is an acetolactate synthase (ALS)-inhibiting herbicide usually applied by post-emergence foliar spraying (PFS) for the control of Echinochloa crus-galli and numerous annual weeds in paddy fields. Herbicides applied by foliar spraying can have negative impacts on the environment, ecosystems, and human health. In this study, the response of E. crus-galli and rice to the PFS and post-emergence water-dispersal (PWD) applications of penoxsulam, and the differences in the detoxification displayed by them between the two treatment methods were compared. The results showed that the PWD application of penoxsulam provides a similar control efficacy against E. crus-galli as PFS at the 1-, 3-, and 5-leaf stages. Meanwhile, the PWD application had a higher safety for the rice. After being treated with 30 g a.i. ha⁻¹ penoxsulam, residues were not detected in the rice treated by the PWD application method, whereas, with the PFS treatment, there was 59.0 µg/kg penoxsulam remaining. With the PFS application, there were many more residues of penoxsulam in the E. crus-galli than with the PWD method; the amount of residues was 32-fold higher 12 h after treatment. The in vitro enzyme activity assays revealed that the activities of ALS, glutathione-S-transferase (GST), and cytochrome P450 monooxygenases (P450) were increased in the PWD treatments, and were 1.5-, 1.3-, and 2.3-fold higher than with PFS 72 h after treatment. The real-time quantitative PCR (qRT-PCR) revealed that the GST1 and P450 genes, CYP81A14, CYP81A12, CYP81A18, and CYP81A21 were upregulated with the PWD application versus PFS in the E. crus-galli. In summary, these results demonstrate that the herbicidal activity was not affected by the upregulation of target and metabolic enzyme activities with the PWD application of penoxsulam. This research could contribute to application strategies reducing the risk of rice injury and environmental impacts by using water-dispersal formulations of penoxsulam. Full article

Shepherd’s-purse (Capsella bursa-pastoris), a globally distributed noxious weed species often found in wheat, has evolved resistance to ALS-inhibiting herbicides mainly due to single mutations in the ALS gene. In the present study, dose–response bioassays showed that a shepherd’s-purse population (R), collected from Xinghua, Jiangsu Province, China, had high level of resistance to the ALS-inhibiting herbicide, mesosulfuron-methyl (800-fold), and even much higher resistance levels to other reported ALS-inhibiting herbicides, tribenuron-methyl (1313-fold), bensulfuron-methyl (969-fold) and penoxsulam (613-fold). Sequencing of the open reading frame of the ALS gene revealed a double ALS gene mutation (Pro197-Ser plus Trp574-Leu) conferring the high resistance in the R plants. Docking analysis of the ALS protein and mesosulfuron-methyl predicts that the two amino acid substitutions in the R samples reduces the binding energy to the herbicide by decreasing the hydrogen bonds (H-bonds) and other interactions, thus endowing resistance to ALS-inhibiting herbicides. These results demonstrate that the double ALS mutation confers high resistance levels to ALS-inhibiting herbicides. To our knowledge, this is the first evidence of the double ALS mutation in shepherd’s-purse endowing ALS-inhibiting herbicide resistance. Full article

A study was carried out to determine the ALS (acetolactate synthase)-inhibitor herbicide resistance in the Mexican grass Ixophorus unisetus, a troublesome weed in corn crops in Mexico. First, the resistance was confirmed in field screening assays. Eight populations that survived nicosulfuron treatment at a field rate of 40 g ai ha⁻¹ were labeled as putative-resistant. Dose–response trials demonstrated a high resistance in the eight populations (GR₅₀ from 140.33 to 245.46 g ai ha⁻¹). The synergism of malathion plus nicosulfuron demonstrated that the non-target-site resistance (NTSR) mechanism based on cytochrome P450 (Cyt-P450) was involved in five populations of I. unisetus. Molecular studies revealed that a single-nucleotide change occurs in the amino acid at position 376 (from GAT to GAG), which codifies from Asp-376 to Glu-376. This is the first time that Asp-376-Glu has been reported in this species. Assays in vitro and in vivo demonstrated I. unisetus cross-resistance to flucarbazone, penoxsulam, bispyribac-Na, and imazamox. No multiple resistance was found in two resistant populations exposed to different herbicides. Our results indicate that the lack of good control over Mexican grass in corn with ALS inhibitors is due to target-site mutation and NTSR mechanisms (Cyt-P450-mediated metabolism). A strategy should be established in Mexican fields to continue controlling this weed, including mechanical control practices and a good combination of the available pre- and post-emergence herbicides. Full article

Water hyacinth (Eichhornia crassipes (Mart). Solms) is a rapidly growing plant that can easily invade water bodies and negatively impact aquatic ecosystems. Cangkuang Lake is currently facing a major issue due to the increased proliferation of this plant species. Although herbicide can be used to manage weeds in aquatic ecosystems to save labor and time, their impact and toxicity on the environment must be considered. Therefore, this study aims to determine the effectiveness of the Florpyrauxifen-benzyl herbicide in controlling water hyacinth in Cangkuang Lake, Garut Regency, West Java, and its impact on water quality. A randomized block design (RBD) was used with eight treatments, and each treatment was replicated four times to obtain a total of 32 experimental plots with a size of 1 m × 1 m. Each plot contained water hyacinth weeds, with a range of 8–10 leaves and a weight range of 250–300 g. The treatment consisted of herbicide with active ingredients Florpyrauxifen-benzyl (5, 15, 25, 35, and 45 g a.i./ha), 2,4-D Dimethyl Amine (DMA) (1200 g a.i./ha), Penoxsulam (25 g a.i./ha), and the control. The study also measured several water quality parameters, including dissolved oxygen (DO), pH, total dissolved solids (TDS), and ammonia levels. The results showed that Florpyrauxifen-benzyl, starting at a dose of 15 g a.i./ha, was effective in controlling E.crassipes weeds with a growth reduction percentage of up to 100% and no weed regrowth at 42 DAA (day after application). However, all water quality parameters were within the standard threshold for the Government Regulation of the Republic of Indonesia No. 22/2021. This study suggests that Florpyrauxifen-benzyl can be an effective herbicide for controlling water hyacinth in Cangkuang Lake, and that its use did not have a negative impact on water quality. However, this study also highlights the importance of considering the potential environmental impact and toxicity of herbicides before their use in aquatic ecosystems. Full article

Smallflower umbrella sedge (Cyperus difformis L.) is an invasive weed, and infestations of C. difformis are increasing in rice (Oryza sativa L.) fields in China. Bensulfuron-methyl is a widely used sulfonylurea herbicide that inhibits the acetolactate synthase (ALS) enzyme and has been used in recent years for effectively controlling annual weeds in the Cyperaceae family. In this study, a suspected resistant population of C. difformis (BBHY1) was collected from a rice field in Huaiyuan County, Anhui Province, China, that survived treatment with bensulfuron-methyl at the field-recommended rate (FRR). Single-dose tests and whole-plant bioassays confirmed that the BBHY1 population was resistant to bensulfuron-methyl and had evolved a high level of resistance, with a resistance index (RI) of 12.87. Sequencing of the ALS gene revealed a CCT to CAT point mutation at codon 197, which caused a P-to-H substitution in the resistant plants. Analysis of the relative expression of ALS revealed no significant differences between the resistant and susceptible populations. Inhibiting the activity of cytochrome P450s (P450s) or glutathione S-transferases (GSTs) had no significant effect on bensulfuron-methyl resistance. The BBHY1 population exhibited cross-resistance to pyrazosulfuron-ethyl, penoxsulam, and bispyribac-sodium, with RIs ranging from 5.48 to 20.63, but remained susceptible to MCPA sodium, florpyrauxifen-benzyl, and bentazon, with RIs of <1.00. These herbicides could be potentially used as alternatives for controlling resistant populations and managing herbicide resistance in other aggressive weeds in rice fields. Full article