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Propylparaben (PrP) and dichloropropylparaben (diClPrP) are found in soil worldwide, mainly due to the incorporation of urban sludge in crop soils and the use of non-raw wastewater for irrigation. Studies on the adverse effects of PrP on plants are incipient and not found for diClPrP. PrP and diClPrP were evaluated at concentrations 4, 40, and 400 µg/L for their phytotoxic potential to seeds of Allium cepa (onion), Cucumis sativus (cucumber), Lycopersicum sculentum (tomato), and Lactuca sativa (lettuce), and cytotoxic, genotoxic potential, and for generating oxygen-reactive substances in root meristems of A. cepa bulbs. PrP and diClPrP caused a significant reduction in seed root elongation in all four species. In A. cepa bulb roots, PrP and diClPrP resulted in a high prophase index; in addition, PrP at 400 µg/L and diClPrP at the three concentrations significantly decreased cell proliferation and caused alterations in a significant number of cells. Furthermore, diClPrP concentrations induced the development of hooked roots in onion bulbs. The two chemical compounds caused significant changes in the modulation of catalase, ascorbate peroxidase, and guaiacol peroxidase, disarming the root meristems against hydroxyl radicals and superoxides. Therefore, PrP and diClPrP were phytotoxic and cytogenotoxic to the species tested, proving dangerous to plants.

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Avobenzone (AVO) is a sunscreen with high global production and is constantly released into the environment. Incorporating sewage biosolids for fertilization purposes, the leaching from cultivated soils, and the use of wastewater for irrigation explain its presence in the soil. There is a lack of information about the impact of this sunscreen on plants. In the present study, the ecotoxicity of AVO was tested at concentrations 1, 10, 100, and 1,000 ng/L. All concentrations caused a reduction in root growth of Allium cepa, Cucumis sativus, and Lycopersicum esculentum seeds, as well as a mitodepressive effect, changes in the mitotic spindle and a reduction in root growth of A. cepa bulbs. The cell cycle was disturbed because AVO disarmed the enzymatic defense system of root meristems, leading to an accumulation of hydroxyl radicals and superoxides, besides lipid peroxidation in cells. Therefore, AVO shows a high potential to cause damage to plants and can negatively affect agricultural production and the growth of non-cultivated plants.

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BACKGROUND: Faced with the need to develop new herbicides with modes of action different to those observed for existing agrochemicals, one of the most promising strategies employed by synthetic chemists involves the structural modification of molecules found in natural products. Molecules containing amides, imides, and epoxides as functional groups are prevalent in nature and find extensive application in synthesizing more intricate compounds due to their biological properties. In this context, this paper delineates the synthesis of N-phenylnorbornenesuccinimide derivatives, conducts biological assays, and carries out in silico investigation of the protein target associated with the most potent compound in plant organisms. The phytotoxic effects of the synthesized compounds (2-29) were evaluated on Allium cepa, Bidens pilosa, Cucumis sativus, Sorghum bicolor, and Solanum lycopersicum. RESULTS: Reaction of endo-bicyclo[2.2.1]hept-5-ene-3a,7a-dicarboxylic anhydride (1) with aromatic amines led to the N-phenylnorbornenesuccinic acids (2-11) with yields ranging from 75% to 90%. Cyclization of compounds (2-11) in the presence of acetic anhydride and sodium acetate afforded N-phenylnorbornenesuccinimides (12-20) with yields varying from 65% to 89%. Those imides were then subjected to epoxidation reaction to afford N-phenylepoxynorbornanesuccimides (21-29) with yields from 60% to 90%. All compounds inhibited the growth of seedlings of the plants evaluated. Substance 23 was the most active against the plants tested, inhibiting 100% the growth of all species in all concentrations. Cyclophilin was found to be the enzymatic target of compound 23. CONCLUSION: These findings suggest that derivatives of N-phenylnorbornenesuccinimide are promising compounds in the quest for more selective and stable agrochemicals. This perspective reinforces the significance of these derivatives as potential innovative herbicides and emphasizes the importance of further exploring their biological activity on weeds. © 2024 Society of Chemical Industry.

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Numerous factors lead to the use of water with saline levels above those suitable for plant development, resulting in negative consequences on crops. Studies have sought techniques that aim to mitigate such consequences and the use of vitamins is promising, since these compounds improve the development conditions of vegetables. Thus, the study aimed to verify the ability of vitamins to mitigate the deleterious effects of using saline water, applied via irrigation during the formation of cucumber seedlings. Cucumber seeds were subjected to imbibition in three vitamin solutions (100 mg L-1thiamine; 100 mg L-1niacin; 50 mg L-1thiamine + 50 mg L-1niacin), in addition to two controls, both with water imbibition . After sowing, irrigation was carried out with saline water (100 mM NaCl), for all treatments, except for one of the controls. It was found that irrigation with saline water affected all variables studied, without, however, having a positive effect from the application of vitamins. Thus, it was concluded that the vitamins were not able to mitigate the deleterious effects caused by the application of saline water under the conditions in which the study was carried out and that future studies should be carried out to evaluate different concentrations and forms of application of the vitamins.

Inúmeros fatores levam à utilização de água com teores salinos acima daqueles adequados ao desenvolvimento vegetal, acarretando consequências negativas sobre os cultivos. Estudos têm buscado técnicas que visem amenizar tais consequências e a utilização de vitaminas é promissora, uma vez que esses compostos melhoram as condições de desenvolvimento dos vegetais. Assim, o estudo teve como objetivo verificar a capacidade das vitaminas em mitigar os efeitos deletérios da utilização de água salina, aplicada via irrigação durante a formação de mudas de pepino. Sementes de pepineiro foram submetidas à embebição em três soluções vitamínicas (100 mg L-1tiamina; 100 mg L-1niacina; 50 mg L-1tiamina + 50 mg L-1niacina), além dois controles, ambos com embebição em água. Após a semeadura a irrigação foi realizada comágua salina (100 mM de NaCl), para todos os tratamentos, com exceção de um dos controles. Verificou-se que a irrigação com água salina afetou todas as variáveis estudas, sem que, no entanto, houvesse efeito positivo da aplicação das vitaminas. Dessa maneira, concluiu-se que as vitaminas não foram capazes de mitigar os efeitos deletérios causados pela aplicação de água salina nas condições em que o estudo foi realizado e que estudos futuros devem ser realizados para avaliar diferentes concentrações e formas de aplicação das vitaminas.

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Numerous factors lead to the use of water with saline levels above those suitable for plant development, resulting in negative consequences on crops. Studies have sought techniques that aim to mitigate such consequences and the use of vitamins is promising, since these compounds improve the development conditions of vegetables. Thus, the study aimed to verify the ability of vitamins to mitigate the deleterious effects of using saline water, applied via irrigation during the formation of cucumber seedlings. Cucumber seeds were subjected to imbibition in three vitamin solutions (100 mg L-1thiamine; 100 mg L-1niacin; 50 mg L-1thiamine + 50 mg L-1niacin), in addition to two controls, both with water imbibition . After sowing, irrigation was carried out with saline water (100 mM NaCl), for all treatments, except for one of the controls. It was found that irrigation with saline water affected all variables studied, without, however, having a positive effect from the application of vitamins. Thus, it was concluded that the vitamins were not able to mitigate the deleterious effects caused by the application of saline water under the conditions in which the study was carried out and that future studies should be carried out to evaluate different concentrations and forms of application of the vitamins.(AU)

Inúmeros fatores levam à utilização de água com teores salinos acima daqueles adequados ao desenvolvimento vegetal, acarretando consequências negativas sobre os cultivos. Estudos têm buscado técnicas que visem amenizar tais consequências e a utilização de vitaminas é promissora, uma vez que esses compostos melhoram as condições de desenvolvimento dos vegetais. Assim, o estudo teve como objetivo verificar a capacidade das vitaminas em mitigar os efeitos deletérios da utilização de água salina, aplicada via irrigação durante a formação de mudas de pepino. Sementes de pepineiro foram submetidas à embebição em três soluções vitamínicas (100 mg L-1tiamina; 100 mg L-1niacina; 50 mg L-1tiamina + 50 mg L-1niacina), além dois controles, ambos com embebição em água. Após a semeadura a irrigação foi realizada comágua salina (100 mM de NaCl), para todos os tratamentos, com exceção de um dos controles. Verificou-se que a irrigação com água salina afetou todas as variáveis estudas, sem que, no entanto, houvesse efeito positivo da aplicação das vitaminas. Dessa maneira, concluiu-se que as vitaminas não foram capazes de mitigar os efeitos deletérios causados pela aplicação de água salina nas condições em que o estudo foi realizado e que estudos futuros devem ser realizados para avaliar diferentes concentrações e formas de aplicação das vitaminas.(AU)

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BACKGROUND: Given the weed resistance to various herbicides with different mechanisms of action, the search for new compounds that are more effective and exhibit low levels of impact to other species in nature has been imperative in the field of the agriculture. For this purpose, 16 phthalides, and furan-2(5H)-one were synthetized and evaluated for their effectiveness as herbicides in seeds of Sorghum bicolor (sorghum), Cucumis sativus (cucumber), and Allium cepa (onion). Furthermore, a preliminary in silico study was carried out to identify the enzyme target of the most active compounds. RESULTS: In the assays with S. bicolor, the mixture rac-(3aR,4R,5S,6S,7S,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one + rac-(3aR,4R,5R,6R,7S,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one (15a + 15b) showed comparable inhibitory activity to (S)-metolachlor, which was used as control herbicide at concentrations ranging from 50 µm to 1000 µm. The developments of the seeds evaluated were altered by all 17 compounds, either stimulating or inhibiting. The best results were presented by compounds 15a, and 15b, either in their pure form or as a mixture. CONCLUSION: The results presented by 15a, and 15b were superior to the activity of the commercial herbicide (S)-metolachlor in the assays with C. sativus, and A. cepa. The in silico study provides strong evidence that the most active compounds bind to strigolactones esterases D14 through the same binding site of (5R)-5-hydroxy-3-methylfuran-2(5H)-one (H3M), which is one of the strigolactones (SLs) cleavage products. © 2019 Society of Chemical Industry.

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BACKGROUND: Despite the need to develop new herbicides with different modes of action, due to weed resistance, many important classes of compounds have been studied poorly for this purpose. Benzoxazoles are considered privileged structures because of their biological activities, but their phytotoxic activities have not received a lot of attention until now. RESULTS: Double vinylic substitution reactions were carried out to furnish four 2-nitromethylbenzoxazoles and one oxazolidine. Benzoxazol-2-ylmethanamine was obtained by reduction of compound 3a. These compounds were evaluated for their phytotoxicity in Allium cepa (onion), Solanum lycopersicum (tomato), Cucumis sativus (cucumber) and Sorghum bicolor (sorghum). Comparison with oxazolidine analogue allowed us to understand that the benzoxazolic structure is very important for the herbicidal activity. CONCLUSION: All the synthesized compounds exhibited biological activity on seed germination. The four 2-nitromethylbenzoxazoles showed phytotoxic activity and the 5-chloro-2-(nitromethyl)benzo[d]oxazole (3b) exhibited higher inhibition than the commercial herbicide against all four plant species tested. © 2018 Society of Chemical Industry.

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The aim of this work was to determine the persistence of auxinic herbicides applied on tropical pasture and toxicity for succeeding crops. The herbicides were applied in an area of dystrophic red‒yellow latosol with pasture infested of weeds. At 40, 80, and 280 days after application of herbicide, the soil samples were collected at depths of 0 to 20 cm. Soil with residues of 2,4-D, 2,4-D + picloram, triclopyr, and a soil without herbicide application were analyzed with six replicates. Seven crops were cultivated in these soils: cucumber (Cucumis sativus L.), velvet bean [Mucuna pruriens (L.) DC.], pigeon pea [Cajanus cajan (L.) Millsp.], alfalfa (Medicago sativa L.), lablab bean [Lablab purpureus (L.) Sweet], corn (Zea mays L.), and sorghum [Sorghum bicolor (L.) Moench]. The plants of cucumber, pigeon pea, and alfalfa were the most susceptible to the auxinic herbicide residues. However, the lablab bean was the only one among the dicot evaluated that showed tolerance to the 2,4-D + picloram residual when cultivated in soils at 280 days after application of herbicide. Corn and sorghum showed lower chlorophyll content in soils with 2,4-D + picloram residual up to 80 days after application of herbicide.

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BACKGROUND: In the context of the demand for more efficient herbicides, the aim of the present work was to synthesize anilides via simple methods, and evaluate their herbicidal activities through seed germination assays. In silico studies were carried out to identify the enzyme target sites in plants for the most active anilides. RESULTS: A total of 18 anilides were prepared via one-pot reaction in yields that varied from 36 to 98% through reactions of anilines with sorbic chloride and hexanoic anhydride. According to seed germination assays in three dicotyledonous and one monocotyledonous plant species, the most active anilides showed root and shoot growth inhibition superior to that of Dual (S-metolachlor). In silico studies indicated that histone deacetylase was the probable enzyme target site in plants for these substances. The affinities of the most active anilides for the binding sites of this enzyme were equal to or higher than those calculated for its inhibitors. CONCLUSION: Anilides 4d, 4e, 4 g, and 4 h are promising candidates for the development of novel herbicides. According to in silico studies, they inhibit histone deacetylase in plants, which can be exploited for the development of new weed control methods. © 2018 Society of Chemical Industry.

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This study evaluated the phytotoxic effects of raw and treated effluents from a swine slaughterhouse on cucumber and lettuce seeds and determined correlations among physicochemical characteristics of such effluents and the germination of seeds used as bioindicators. Physicochemical parameters were characterized for both effluents and their phytotoxicity was determined through the germination index (GI), the root length (RL) and the number of germinated seeds (SG) for both plant species. The effluents treatment system was efficient to reduce the concentration of some physicochemical parameters to levels within those recommended by the Brazilian legislation, except for P, ammoniacal N and TKN concentration. Although phytotoxicity of the treated effluent was less in comparison to the raw effluent, the GI for cucumber and lettuce seeds submitted to each of the tested effluents was lower than 80%. Thus, both effluents were phytotoxic for the tested bioindicators (p<0.05). For lettuce seeds, the GI presented negative correlations (p<0.05) with the total Kjeldahl N (-0.93) and the surfactants concentration (-0.83) in the raw effluent. The Zn concentration in the treated effluent showed a negative correlation (p<0.05) with the GI of both lettuce (-0.63) and cucumber seeds (-0.64). Therefore, effluents from swine slaughterhouses may impair the germination of the evaluated plant species if used for agricultural purposes.

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