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1.
Sci Rep ; 14(1): 10544, 2024 05 08.
Artículo en Inglés | MEDLINE | ID: mdl-38719860

RESUMEN

The increasing amount of weeds surviving herbicide represents a very serious problem for crop management. The interaction between microbial community of soil and herbicide resistance, along with the potential evolutive consequences, are still poorly known and need to be investigated to better understand the impact on agricultural management. In our study, we analyzed the microbial composition of soils in 32 farms, located in the Northern Italy rice-growing area (Lombardy) with the aim to evaluate the relationship between the microbial composition and the incidence of resistance to acetolactate synthase (ALS) and acetyl-CoA carboxylase (ACCase) inhibiting herbicides in Echinochloa species. We observed that the coverage of weeds survived herbicide treatment was higher than 60% in paddy fields with a low microbial biodiversity and less than 5% in those with a high microbial biodiversity. Fungal communities showed a greater reduction in richness than Bacteria. In soils with a reduced microbial diversity, a significant increase of some bacterial and fungal orders (i.e. Lactobacillales, Malasseziales and Diaporthales) was observed. Interestingly, we identified two different microbial profiles linked to the two conditions: high incidence of herbicide resistance (H-HeR) and low incidence of herbicide resistance (L-HeR). Overall, the results we obtained allow us to make hypotheses on the greater or lesser probability of herbicide resistance occurrence based on the composition of the soil microbiome and especially on the degree of biodiversity of the microbial communities.


Asunto(s)
Acetolactato Sintasa , Acetil-CoA Carboxilasa , Echinochloa , Resistencia a los Herbicidas , Herbicidas , Microbiología del Suelo , Italia/epidemiología , Herbicidas/farmacología , Acetolactato Sintasa/antagonistas & inhibidores , Acetolactato Sintasa/genética , Echinochloa/efectos de los fármacos , Acetil-CoA Carboxilasa/genética , Acetil-CoA Carboxilasa/antagonistas & inhibidores , Malezas/efectos de los fármacos , Microbiota/efectos de los fármacos , Biodiversidad , Bacterias/efectos de los fármacos , Bacterias/genética , Bacterias/aislamiento & purificación , Bacterias/clasificación , Suelo/química , Hongos/efectos de los fármacos , Hongos/aislamiento & purificación , Hongos/genética
2.
J Agric Food Chem ; 72(19): 10772-10780, 2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38703122

RESUMEN

Protoporphyrinogen IX oxidase (PPO, E.C. 1.3.3.4) plays a pivotal role in chlorophyll biosynthesis in plants, making it a prime target for herbicide development. In this study, we conducted an investigation aimed at discovering PPO-inhibiting herbicides. Through this endeavor, we successfully identified a series of novel compounds based on the pyridazinone scaffold. Following structural optimization and biological assessment, compound 10ae, known as ethyl 3-((6-fluoro-5-(6-oxo-4-(trifluoromethyl)pyridazin-1(6H)-yl)benzo[d]thiazol-2-yl)thio)propanoate, emerged as a standout performer. It exhibited robust activity against Nicotiana tabacum PPO (NtPPO) with an inhibition constant (Ki) value of 0.0338 µM. Concurrently, we employed molecular simulations to obtain further insight into the binding mechanism with NtPPO. Additionally, another compound, namely, ethyl 2-((6-fluoro-5-(5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1(6H)-yl)benzo[d]thiazol-2-yl)thio)propanoate (10bh), demonstrated broad-spectrum and highly effective herbicidal properties against all six tested weeds (Leaf mustard, Chickweed, Chenopodium serotinum, Alopecurus aequalis, Poa annua, and Polypogon fugax) at the dosage of 150 g a.i./ha through postemergence application in a greenhouse. This work identified a novel lead compound (10bh) that showed good activity in vitro and excellent herbicidal activity in vivo and had promising prospects as a new PPO-inhibiting herbicide lead.


Asunto(s)
Diseño de Fármacos , Inhibidores Enzimáticos , Herbicidas , Nicotiana , Proteínas de Plantas , Protoporfirinógeno-Oxidasa , Piridazinas , Protoporfirinógeno-Oxidasa/antagonistas & inhibidores , Protoporfirinógeno-Oxidasa/metabolismo , Protoporfirinógeno-Oxidasa/química , Protoporfirinógeno-Oxidasa/genética , Piridazinas/química , Piridazinas/farmacología , Herbicidas/farmacología , Herbicidas/química , Herbicidas/síntesis química , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/síntesis química , Relación Estructura-Actividad , Nicotiana/metabolismo , Nicotiana/enzimología , Proteínas de Plantas/química , Proteínas de Plantas/metabolismo , Proteínas de Plantas/antagonistas & inhibidores , Proteínas de Plantas/genética , Simulación del Acoplamiento Molecular , Estructura Molecular , Malezas/efectos de los fármacos , Malezas/enzimología , Cinética
3.
J Environ Sci Health B ; 59(6): 350-360, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38736380

RESUMEN

The aim of this study was to assess the efficacy of herbicides in association to control Rottboellia exaltata and Ipomoea quamoclit during pre-emergence while also to evaluate the potential impact on the sugarcane. The experimental design employed a randomized block with seven treatments and four replications. The treatments were: 1 - no herbicide application; 2 - indaziflam + sulfentrazone; 3 - indaziflam + diclosulam; 4 - indaziflam + tebuthiuron; 5 - flumioxazin + diclosulam, 6 - flumioxazin + pyroxasulfone and 7 - clomazone + sulfentrazone. The evaluated parameters were: percentage of weeds control, green coverage percentage (Canopeo® system), weed biomass (g m-2), itchgrass height, and sugarcane tiller. Several herbicide associations have been proven effective alternatives for managing itchgrass and cypressvine morningglory. The most successful treatments for itchgrass control were indaziflam + tebuthiuron (100%) and indaziflam + diclosulam (97%), whereas for cypressvine morningglory, the betters were indaziflam + sulfentrazone (97%), indaziflam + diclosulam (98%), indaziflam + tebuthiuron (97%), flumioxazin + diclosulam (94%), and clomazone + sulfentrazone (96%). All treatments reduced the weed biomass, with indaziflam + tebuthiuron being the safest option for protecting sugarcane.


Asunto(s)
Herbicidas , Saccharum , Control de Malezas , Herbicidas/farmacología , Control de Malezas/métodos , Malezas/efectos de los fármacos , Ipomoea/efectos de los fármacos
4.
J Agric Food Chem ; 72(20): 11405-11414, 2024 May 22.
Artículo en Inglés | MEDLINE | ID: mdl-38717990

RESUMEN

This study investigated the multiple herbicide resistance (MHR) mechanism of one Echinochloa crus-galli population that was resistant to florpyrauxifen-benzyl (FPB), cyhalofop-butyl (CHB), and penoxsulam (PEX). This population carried an Ala-122-Asn mutation in the acetolactate synthase (ALS) gene but no mutation in acetyl-CoA carboxylase (ACCase) and transport inhibitor response1 (TIR1) genes. The metabolism rate of PEX was 2-fold higher, and the production of florpyrauxifen-acid and cyhalofop-acid was lower in the resistant population. Malathion and 4-chloro-7-nitrobenzoxadiazole (NBD-Cl) could reverse the resistance, suggesting that cytochrome P450 (CYP450) and glutathione S-transferase (GST) contribute to the enhanced metabolism. According to RNA-seq and qRT-PCR validation, two CYP450 genes (CYP71C42 and CYP71D55), one GST gene (GSTT2), two glycosyltransferase genes (rhamnosyltransferase 1 and IAAGLU), and two ABC transporter genes (ABCG1 and ABCG25) were induced by CHB, FPB, and PEX in the resistant population. This study revealed that the target mutant and enhanced metabolism were involved in the MHR mechanism in E. crus-galli.


Asunto(s)
Sistema Enzimático del Citocromo P-450 , Echinochloa , Resistencia a los Herbicidas , Herbicidas , Mutación , Proteínas de Plantas , Resistencia a los Herbicidas/genética , Herbicidas/farmacología , Herbicidas/metabolismo , Echinochloa/genética , Echinochloa/efectos de los fármacos , Echinochloa/metabolismo , Echinochloa/crecimiento & desarrollo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Sistema Enzimático del Citocromo P-450/genética , Sistema Enzimático del Citocromo P-450/metabolismo , Acetil-CoA Carboxilasa/genética , Acetil-CoA Carboxilasa/metabolismo , Malezas/efectos de los fármacos , Malezas/genética , Malezas/metabolismo , Acetolactato Sintasa/genética , Acetolactato Sintasa/metabolismo , Butanos , Nitrilos , Sulfonamidas , Uridina/análogos & derivados
5.
Funct Plant Biol ; 512024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38769679

RESUMEN

The two stresses of weed competition and salt salinity lead to crop yield losses and decline in the productivity of agricultural land. These constraints threaten the future of food production because weeds are more salt stress tolerant than most crops. Climate change will lead to an increase of soil salinity worldwide, and possibly exacerbate the competition between weeds and crops. This aspect has been scarcely investigated in the context of weed-crop competition. Therefore, we conducted a field experiment on green beans (Phaseolus vulgaris ) to investigate the combined impact of weed competition and salt stress on key morpho-physiological traits, and crop yield. We demonstrated that soil salinity shifted weed composition toward salt tolerant weed species (Portulaca oleracea and Cynodon dactylon ), while it reduced the presence of lower tolerance species. Weed competition activated adaptation responses in green bean such as reduced leaf mass per area and biomass allocation to the stem, unchanged stomatal density and instantaneous water use efficiency, which diverge from those that are typically observed as a consequence of salt stress. The morpho-physiological modifications caused by weeds is attributed to the alterations of light intensity and/or quality, further confirming the pivotal role of the light in crop response to weeds. We concluded that higher yield loss caused by combined salt stress and weed competition is due to impaired morpho-physiological responses, which highlights the negative interaction between salt stress and weed competition. This phenomenon will likely be more frequent in the future, and potentially reduce the efficacy of current weed control methods.


Asunto(s)
Adaptación Fisiológica , Phaseolus , Malezas , Estrés Salino , Phaseolus/fisiología , Phaseolus/efectos de los fármacos , Malezas/efectos de los fármacos , Malezas/fisiología , Hojas de la Planta/fisiología , Hojas de la Planta/efectos de los fármacos , Productos Agrícolas/crecimiento & desarrollo , Salinidad , Suelo/química , Biomasa
6.
Physiol Plant ; 176(3): e14324, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38705866

RESUMEN

Broomrape (Orobanche cumana) negatively affects sunflower, causing severe yield losses, and thus, there is a need to control O. cumana infestation. Brassinosteroids (BRs) play key roles in plant growth and provide resilience to weed infection. This study aims to evaluate the mechanisms by which BRs ameliorate O. cumana infection in sunflower (Helianthus annuus). Seeds were pretreated with BRs (1, 10, and 100 nM) and O. cumana inoculation for 4 weeks under soil conditions. O. cumana infection significantly reduced plant growth traits, photosynthesis, endogenous BRs and regulated the plant defence (POX, GST), BRs signalling (BAK1, BSK1 to BSK4) and synthesis (BRI1, BR6OX2) genes. O. cumana also elevated the levels of malondialdehyde (MDA), hydroxyl radical (OH-), hydrogen peroxide (H2O2) and superoxide (O2 •-) in leaves/roots by 77/112, 63/103, 56/97 and 54/89%, as well as caused ultrastructural cellular damages in both leaves and roots. In response, plants activated a few enzymes, superoxide dismutase (SOD), peroxidase (POD) and reduced glutathione but were unable to stimulate the activity of ascorbate peroxidase (APX) and catalase (CAT) enzymes. The addition of BRs (especially at 10 nM) notably recovered the ultrastructural cellular damages, lowered the production of oxidative stress, activated the key enzymatic antioxidants and induced the phenolic and lignin contents. The downregulation in the particular genes by BRs is attributed to the increased resilience of sunflower via a susceptible reaction. In a nutshell, BRs notably enhanced the sunflower resistance to O. cumana infection by escalating the plant immunity responses, inducing systemic acquired resistance, reducing oxidative or cellular damages, and modulating the expression of BR synthesis or signalling genes.


Asunto(s)
Brasinoesteroides , Helianthus , Orobanche , Semillas , Helianthus/efectos de los fármacos , Helianthus/inmunología , Helianthus/fisiología , Brasinoesteroides/farmacología , Brasinoesteroides/metabolismo , Orobanche/fisiología , Orobanche/efectos de los fármacos , Semillas/efectos de los fármacos , Semillas/inmunología , Malezas/efectos de los fármacos , Malezas/fisiología , Enfermedades de las Plantas/parasitología , Enfermedades de las Plantas/inmunología , Inmunidad de la Planta/efectos de los fármacos , Regulación de la Expresión Génica de las Plantas/efectos de los fármacos , Fotosíntesis/efectos de los fármacos , Raíces de Plantas/inmunología , Raíces de Plantas/efectos de los fármacos , Peróxido de Hidrógeno/metabolismo , Hojas de la Planta/efectos de los fármacos , Hojas de la Planta/inmunología , Proteínas de Plantas/metabolismo , Proteínas de Plantas/genética , Malondialdehído/metabolismo
7.
Sci Rep ; 14(1): 10356, 2024 05 06.
Artículo en Inglés | MEDLINE | ID: mdl-38710732

RESUMEN

Herbicide use may pose a risk of environmental pollution or evolution of resistant weeds. As a result, an experiment was carried out to assess the influence of different non-chemical weed management tactics (one hoeing (HH) at 12 DAS followed by (fb) one hand weeding at 30 DAS, one HH at 12 DAS fb Sesbania co-culture and its mulching, one HH at 12 DAS fb rice straw mulching @ 4t ha-1, one HH at 12 DAS fb rice straw mulching @ 6 t ha-1) on weed control, crop growth and yield, and economic returns in direct-seeded rice (DSR). Experiment was conducted during kharif season in a split-plot design and replicated thrice. Zero-till seed drill-sown crop (PN) had the lowest weed density at 25 days after sowing (DAS), while square planting geometry (PS) had the lowest weed density at 60 DAS. PS also resulted in a lower weed management index (WMI), agronomic management index (AMI), and integrated weed management index (IWMI), as well as higher growth attributes, grain yield (4.19 t ha-1), and net return (620.98 US$ ha-1). The cultivar Arize 6444 significantly reduced weed density and recorded higher growth attributes, yield, and economic return. In the case of weed management treatments, one HH at 12 DAS fb Sesbania co-culture and its mulching had the lowest weed density, Shannon-weinner index and eveness at 25 DAS. However, one hoeing at 12 DAS fb one hand weeding at 30 DAS (HH + WH) achieved the highest grain yield (4.85 t ha-1) and net returns (851.03 US$ ha-1) as well as the lowest weed density at 60 DAS. PS × HH + WH treatment combination had the lowest weed persistent index (WPI), WMI, AMI, and IWMI, and the highest growth attributes, production efficiency, and economic return.


Asunto(s)
Productos Agrícolas , Oryza , Malezas , Control de Malezas , Oryza/crecimiento & desarrollo , Control de Malezas/métodos , Malezas/crecimiento & desarrollo , Malezas/efectos de los fármacos , Productos Agrícolas/crecimiento & desarrollo , Agricultura/métodos , Semillas/crecimiento & desarrollo , Semillas/efectos de los fármacos , Herbicidas/farmacología , Producción de Cultivos/métodos
8.
Chemosphere ; 358: 142087, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38657696

RESUMEN

Bidens pilosa is classified as an invasive plant and has become a problematic weed to many agricultural crops. This species strongly germinates, grows and reproduces and competing for nutrients with local plants. To lessen the influence of Bidens pilosa, therefore, converting this harmful species into carbon materials as adsorbents in harm-to-wealth and valorization strategies is required. Here, we synthesized a series of magnetic composites based on MFe2O4 (M = Ni, Co, Zn, Fe) supported on porous carbon (MFOAC) derived from Bidens pilosa by a facile hydrothermal method. The Bidens pilosa carbon was initially activated by condensed H3PO4 to increase the surface chemistry. We observed that porous carbon loaded NiFe2O4 (NFOAC) reached the highest surface area (795.7 m2 g-1), followed by CoFe2O4/AC (449.1 m2 g-1), Fe3O4/AC (426.1 m2 g-1), ZnFe2O4/AC (409.5 m2 g-1). Morphological results showed nanoparticles were well-dispersed on the surface of carbon. RhB, MO, and MR dyes were used as adsorbate to test the adsorption by MFOAC. Effect of time (0-360 min), concentration (5-50 mg L-1), dosage (0.05-0.2 g L-1), and pH (3-9) on dyes adsorption onto MFOAC was investigated. It was found that NFOAC obtained the highest maximum adsorption capacity against dyes, RhB (107.96 mg g-1) < MO (148.05 mg g-1) < MR (153.1 mg g-1). Several mechanisms such as H bonding, π-π stacking, cation-π interaction, and electrostatic interaction were suggested. With sufficient stability and capacity, NFOAC can be used as potential adsorbent for real water treatment systems.


Asunto(s)
Bidens , Carbono , Colorantes , Compuestos Férricos , Adsorción , Bidens/química , Porosidad , Carbono/química , Compuestos Férricos/química , Colorantes/química , Níquel/química , Contaminantes Químicos del Agua/química , Zinc/química , Malezas/efectos de los fármacos , Cobalto/química
9.
Pestic Biochem Physiol ; 201: 105911, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38685231

RESUMEN

Ammannia auriculata Willd. is a noxious broadleaf weed, commonly infesting rice ecosystems across southern China. A putative resistant A. auriculata population (AHSC-5) was sampled from a rice field of Anhui Province, where bensulfuron-methyl (BM) was unable to control its occurrence. This study aimed to determine the sensitivities of the AHSC-5 population to common-use herbicides, and to investigate the underlying resistance mechanisms. The bioassays showed that the AHSC-5 population was 138.1-fold resistant to BM, compared with the susceptible population (JSGL-1). Pretreatment of malathion reduced the resistance index to 19.5. ALS sequencing revealed an Asp376Glu substitution in the AHSC-5 population, and in vitro ALS activity assays found that 50% activity inhibition (I50) of BM in AHSC-5 was 75.4 times higher than that of JSGL-1. Moreover, the AHSC-5 population displayed cross-resistance to pyrazosulfuron-ethyl (10.6-fold), bispyribac­sodium (3.6-fold), and imazethapyr (2.2-fold), and was in the process of evolving multiple resistance to synthetic auxin herbicides fluroxypyr (2.3-fold) and florpyrauxifen-benzyl (3.1-fold). This study proved the BM resistance in A. auriculata caused by the Asp376Glu mutation and P450-regulated metabolism. This multi-resistant population can still be controlled by penoxsulam, MCPA, bentazone, and carfentrazone-ethyl, which aids in developing targeted and effective weed management strategies.


Asunto(s)
Acetolactato Sintasa , Sistema Enzimático del Citocromo P-450 , Resistencia a los Herbicidas , Herbicidas , Acetolactato Sintasa/genética , Acetolactato Sintasa/antagonistas & inhibidores , Herbicidas/farmacología , Resistencia a los Herbicidas/genética , Sistema Enzimático del Citocromo P-450/genética , Sistema Enzimático del Citocromo P-450/metabolismo , Malatión/farmacología , Compuestos de Sulfonilurea/farmacología , Malezas/efectos de los fármacos , Malezas/genética , Sustitución de Aminoácidos
10.
Pestic Biochem Physiol ; 201: 105908, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38685229

RESUMEN

The inclination toward natural products has led to the onset of the discovery of new bioactive metabolites that could be targeted for specific therapeutic or agronomic applications. Despite increasing knowledge coming to light of plant-derived materials as leads for new herbicides, relatively little is known about the mode of action on herbicide-resistant weeds. Cyanamide (CA) is a naturally occurring herbicide synthesized by hairy vetch (Vicia villosa Roth.). However, it has not been experimentally verified whether CA suppresses target plants via sustained discharge at low concentrations, as is often the case with most plant-derived materials. This study aimed to detect the toxicity and the mode of action of CA to alfalfa (Medicago sativa L.) and redroot pigweed (Amaranthus retroflexus L.). The toxicity of CA toward the alfalfa and redroot pigweed by three different exposure patterns was compared: low-concentration repeated exposure with 0.3 g/L CA (LRE), high-concentration single exposure with 1.2 g/L CA (HSE), and distilled water spray as control. The results showed that CA had a stronger inhibitory effect on redroot pigweed growth compared to alfalfa under both LRE and HSE exposure modes, with leaves gradually turning yellow and finally wilting. Beyond that, field trials were conducted to corroborate the toxicity of CA to alfalfa and redroot pigweed. The results have also shown that CA could inhibit the growth of redroot pigweed without significant adverse effects on alfalfa. The outcomes concerning electrolyte permeability, root activity, and malondialdehyde (MDA) content indicated that CA suppressed the growth of redroot pigweed by interfering with the structure of the cell membrane and impacting cellular osmotic potential. CA could destroy the cell membrane structure to inhibit the growth of the redroot pigweed by both LRE and HSE exposure modes, which provides a theoretical basis for preventing and controlling redroot pigweed in alfalfa fields.


Asunto(s)
Amaranthus , Cianamida , Herbicidas , Medicago sativa , Medicago sativa/efectos de los fármacos , Herbicidas/toxicidad , Herbicidas/farmacología , Amaranthus/efectos de los fármacos , Cianamida/farmacología , Malondialdehído/metabolismo , Malezas/efectos de los fármacos
11.
J Agric Food Chem ; 72(18): 10218-10226, 2024 May 08.
Artículo en Inglés | MEDLINE | ID: mdl-38666644

RESUMEN

In this work, a series of pyrrolidinone-containing 2-phenylpyridine derivatives were synthesized and evaluated as novel protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) inhibitors for herbicide development. At 150 g ai/ha, compounds 4d, 4f, and 4l can inhibit the grassy weeds of Echinochloa crus-galli (EC), Digitaria sanguinalis (DS), and Lolium perenne (LP) with a range of 60 to 90%. Remarkably, at 9.375 g ai/ha, these compounds showed 100% inhibition effects against broadleaf weeds of Amaranthus retroflexus (AR) and Abutilon theophrasti (AT), which were comparable to the performance of the commercial herbicides flumioxazin (FLU) and saflufenacil (SAF) and better than that of acifluorfen (ACI). Molecular docking analyses revealed significant hydrogen bonding and π-π stacking interactions between compounds 4d and 4l with Arg98, Asn67, and Phe392, respectively. Additionally, representative compounds were chosen for in vivo assessment of PPO inhibitory activity, with compounds 4d, 4f, and 4l demonstrating excellent inhibitory effects. Notably, compounds 4d and 4l induced the accumulation of reactive oxygen species (ROS) and a reduction in the chlorophyll (Chl) content. Consequently, compounds 4d, 4f, and 4l are promising lead candidates for the development of novel PPO herbicides.


Asunto(s)
Diseño de Fármacos , Inhibidores Enzimáticos , Herbicidas , Simulación del Acoplamiento Molecular , Malezas , Protoporfirinógeno-Oxidasa , Pirrolidinonas , Protoporfirinógeno-Oxidasa/antagonistas & inhibidores , Protoporfirinógeno-Oxidasa/química , Protoporfirinógeno-Oxidasa/metabolismo , Herbicidas/farmacología , Herbicidas/química , Herbicidas/síntesis química , Malezas/efectos de los fármacos , Malezas/enzimología , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/síntesis química , Relación Estructura-Actividad , Pirrolidinonas/química , Pirrolidinonas/farmacología , Pirrolidinonas/síntesis química , Proteínas de Plantas/química , Proteínas de Plantas/antagonistas & inhibidores , Piridinas/química , Piridinas/farmacología , Piridinas/síntesis química , Amaranthus/efectos de los fármacos , Amaranthus/química , Echinochloa/efectos de los fármacos , Echinochloa/enzimología , Digitaria/efectos de los fármacos , Digitaria/enzimología , Digitaria/química , Lolium/efectos de los fármacos , Lolium/enzimología , Estructura Molecular
12.
Pest Manag Sci ; 80(6): 2639-2646, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38288581

RESUMEN

BACKGROUND: The discovery of lead compounds is fundamental to herbicide innovation, yet the limited availability of valuable lead compounds has impeded their progress in recent years. The study presents a novel molecular scaffold that exhibits remarkably potent herbicidal activity. RESULTS: Through a scaffold-hopping strategy, a highly potent lead compound for herbicides, namely 3-(2-pyridinyl)-benzothiazol-2-one, was unexpectedly discovered during attempts to structurally modify haloxyfop, a commercial aryl-oxy-phenoxy-propionate herbicide. To investigate the structure-activity relationship (SAR) of the newly discovered herbicidal chemicals, a series of 2-(2-oxo-3-(pyridin-2-yl)-2,3-dihydrobenzo[d]thiazol-6-yloxy)propanoic acid derivatives, I-01 ~ I-27, were designed and synthesized. SAR analysis revealed that trifluoromethyl at the 5-position of pyridine is crucial for herbicidal activity, whereas additional fluorine or Cl atom at the 3-position of pyridine significantly enhances activity. Carboxylic ester derivatives exhibit superior herbicidal activity compared with amide derivatives. Moreover, the activity of carboxylic ester derivatives decreases with C chain extension, but the introduction of O atoms in the side chain benefits activity enhancement. Pot experiments conducted in a glasshouse demonstrated that I-01 and I-09 exhibited potent postemergence herbicidal activity against broadleaf weeds, and completely inhibited growth of Amaranthus retroflex, Abutilon theophrasti and Portulaca oleracea at a dosage of 75 g ha-1. CONCLUSION: Despite the initial goal of scaffold-hopping not being achieved, we have successfully identified a novel molecular scaffold exhibiting exceptional herbicidal activity, thereby presenting innovative prospects for herbicide development. © 2024 Society of Chemical Industry.


Asunto(s)
Herbicidas , Malezas , Herbicidas/farmacología , Herbicidas/síntesis química , Herbicidas/química , Relación Estructura-Actividad , Malezas/efectos de los fármacos , Propionatos/farmacología , Propionatos/síntesis química , Propionatos/química
13.
Sci Rep ; 12(1): 13476, 2022 08 05.
Artículo en Inglés | MEDLINE | ID: mdl-35931689

RESUMEN

Plant species with allelopathic effects against weeds have emerged as a potential strategy for the development of ecologically friendly bioherbicides. In this study, the allelopathic effects of the plant species Dipteryx lacunifera Ducke, Ricinus communis L., Piper tuberculatum Jacq., and Jatropha gossypiifolia L. on the weed Bidens bipinnata L. were investigated. In vitro bioassays revealed that aqueous extracts of selected plant species were able to inhibit seed germination and seedling growth of B. bipinnata, highlighting the strongest allelopathic effect evidenced by R. communis. The phytotoxicity of the aqueous extracts was evaluated in pot experiments, which indicated that the foliar application of R. communis and P. tuberculatum extracts on B. bipinnata plants caused yellowing of leaves, affecting the chlorophyll content and reducing growth. The discrimination of the plant extracts by attenuated total reflectance Fourier transform mid-infrared (ATR FT-MIR) spectroscopy combined with principal component analysis (PCA) indicated the presence of allelochemical compounds, such as phenolics and terpenoids, which may be associated with allelopathic activity. Overall, this study provides valuable information about the substantial allelopathic inhibitory effects of the plant species R. communis and P. tuberculatum on the weed B. bipinnata, which may be used for the development of eco-friendly bioherbicides.


Asunto(s)
Alelopatía , Bidens , Herbicidas , Bidens/efectos de los fármacos , Germinación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Malezas/efectos de los fármacos
14.
Sci Rep ; 12(1): 2518, 2022 02 15.
Artículo en Inglés | MEDLINE | ID: mdl-35169256

RESUMEN

Stacking multiple genes into cotton crop to cop up multiple biotic stresses such as insects and weeds is a promising tool to save crop from losses. Transgenic cotton variety, VH-289, with double Bt and cp4EPSPS genes under the control of 35S promoter was used for the expression analyses and biosafety studies. The transgenic cotton plants were screened through PCR amplification of fragments, 1.7 kb for Cry1Ac, 582 bp for Cry2A and 250 bp for cp4EPSPS; which confirmed the presence of all genes transformed in transgenic cotton. The Cry1Ac + Cry2A and cp4EPSPS proteins were quantified through ELISA in transgenic cotton plants. The Glyphosate assay performed by spraying 1900 mL per acre of glyphosate Roundup further confirmed complete survival of transgenic cotton plants as compared to the non-transgenic cotton plants and all weeds. Similarly, insect infestation data determined that almost 99% insect mortality was observed in controlled field grown transgenic cotton plants as compared to the non-transgenic control plants. Evaluation of effect of temperature and soil nutrients availability on transgene expression in cotton plants was done at two different cotton growing regions, Multan and Lahore, Pakistan and results suggested that despite of higher temperature in Multan field, an increased level of Cry and cp4EPSPS proteins was recorded due to higher soil organic matter availability compared to Lahore field. Before commercialization of any transgenic variety its biosafety study is mandatory so, a 90 days biosafety study of the transgenic cotton plants with 40% transgenic cottonseeds in standard diet showed no harmful effect on wister rat model when studied for liver function, renal function and serum electrolyte.


Asunto(s)
Glicina/análogos & derivados , Gossypium/efectos de los fármacos , Gossypium/genética , Resistencia a los Herbicidas/genética , Herbicidas/farmacología , Lepidópteros , Malezas/efectos de los fármacos , Animales , Dieta/métodos , Endotoxinas/genética , Endotoxinas/metabolismo , Glicina/farmacología , Gossypium/metabolismo , Proteínas Hemolisinas/genética , Proteínas Hemolisinas/metabolismo , Larva , Pruebas de Función Hepática , Masculino , Modelos Animales , Pakistán , Hojas de la Planta/genética , Hojas de la Planta/metabolismo , Plantas Modificadas Genéticamente/efectos de los fármacos , Plantas Modificadas Genéticamente/metabolismo , Ratas , Ratas Wistar , Medición de Riesgo , Semillas/genética , Semillas/metabolismo , Transgenes , Glifosato
15.
BMC Plant Biol ; 22(1): 84, 2022 Feb 24.
Artículo en Inglés | MEDLINE | ID: mdl-35209839

RESUMEN

BACKGROUND: Certain Fusarium exometabolites have been reported to inhibit seed germination of the cereal-parasitizing witchweed, Striga hermonthica, in vitro. However, it is unknown if these exometabolites will consistently prevent S. hermonthica incidence in planta. The study screened a selection of known, highly phytotoxic Fusarium exometabolites, in identifying the most potent/efficient candidate (i.e., having the greatest effect at minimal concentration) to completely hinder S. hermonthica seed germination in vitro and incidence in planta, without affecting the host crop development and yield. RESULTS: In vitro germination assays of the tested Fusarium exometabolites (i.e., 1,4-naphthoquinone, equisetin, fusaric acid, hymeglusin, neosolaniol (Neo), T-2 toxin (T-2) and diacetoxyscirpenol (DAS)) as pre-Striga seed conditioning treatments at 1, 5, 10, 20, 50 and 100 µM, revealed that only DAS, out of all tested exometabolites, completely inhibited S. hermonthica seed germination at each concentration. It was followed by T-2 and Neo, as from 10 to 20 µM respectively. The remaining exometabolites reduced S. hermonthica seed germination as from 20 µM (P < 0. 0001). In planta assessment (in a S. hermonthica-sorghum parasitic system) of the exometabolites at 20 µM showed that, although, none of the tested exometabolites affected sorghum aboveground dry biomass (P > 0.05), only DAS completely prevented S. hermonthica incidence. Following a 14-d incubation of DAS in the planting soil substrate, bacterial 16S ribosomal RNA (rRNA) and fungal 18S rRNA gene copy numbers of the soil microbial community were enhanced; which coincided with complete degradation of DAS in the substrate. Metabolic footprinting revealed that the S. hermonthica mycoherbicidal agent, Fusarium oxysporum f. sp. strigae (isolates Foxy-2, FK3), did not produce DAS; a discovery that corresponded with underexpression of key genes (Tri5, Tri4) necessary for Fusarium trichothecene biosynthesis (P < 0.0001). CONCLUSIONS: Among the tested Fusarium exometabolites, DAS exhibited the most promising herbicidal potential against S. hermonthica. Thus, it could serve as a new biocontrol agent for efficient S. hermonthica management. Further examination of DAS specific mode of action against the target weed S. hermonthica at low concentrations (≤ 20 µM), as opposed to non-target soil organisms, is required.


Asunto(s)
Fusarium/metabolismo , Herbicidas/farmacología , Malezas/efectos de los fármacos , Tricotecenos/farmacología , Germinación/efectos de los fármacos , Semillas/efectos de los fármacos , Microbiología del Suelo , Striga , Tricotecenos/metabolismo
16.
PLoS One ; 17(1): e0262586, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35085310

RESUMEN

Synthetic fertilizer and herbicides encompass the largest share in nutrient and weed management on food grain crops that create serious environmental issues. Integrated nutrient and non-chemical weed management approaches may help to reduce the chemical load in the environment, maintaining higher weed control efficiency and yield. A field experiment was conducted for two consecutive monsoon seasons during 2015 and 2016 in farm fields to develop a profitable and sustainable rice production system through integrated nutrient and weed management practices. A varied combination of nutrients either alone or integrated with chemical and non-chemical weed management were tested on transplanted rice in a factorial randomized block design with three replications. The results showed that the integration of concentrated organic manures with chemical fertilizer effectively inhibited weed growth and nutrient removal. Integration of nutrient and weed management practices significantly enhanced 9% biomass growth, 10% yield of the rice crop along with 3-7% higher nutrient uptake. Brassicaceous seed meal (BSM) and neem cake also had some influence on weed suppression and economic return. Thus, the integrated nutrient and weed management practices in rice cultivation might be an effective way to achieve economic sustainability and efficient rice cultivation in eastern India. Shortages of farmyard manure and vermicompost could be supplemented by BSM and neem cake in the integrated module.


Asunto(s)
Oryza/efectos de los fármacos , Oryza/crecimiento & desarrollo , Malezas/efectos de los fármacos , Malezas/crecimiento & desarrollo , Suelo/química , Agricultura/métodos , Biomasa , Carbono/química , Productos Agrícolas/efectos de los fármacos , Fertilidad/efectos de los fármacos , Fertilizantes , Herbicidas/farmacología , India , Estiércol , Nitrógeno/química , Nutrientes/química , Fósforo/química , Semillas/efectos de los fármacos , Semillas/crecimiento & desarrollo
17.
Plant Physiol ; 188(2): 1369-1384, 2022 02 04.
Artículo en Inglés | MEDLINE | ID: mdl-34850204

RESUMEN

The obligate hemiparasitic weed Striga hermonthica grows on cereal roots and presents a severe threat to global food security by causing enormous yield losses, particularly in sub-Saharan Africa. The rapidly increasing Striga seed bank in infested soils provides a major obstacle in controlling this weed. Striga seeds require host-derived strigolactones (SLs) for germination, and corresponding antagonists could be used as germination inhibitors. Recently, we demonstrated that the common detergent Triton X-100 is a specific inhibitor of Striga seed germination by binding noncovalently to its receptor, S. hermonthica HYPO-SENSITIVE TO LIGHT 7 (ShHTL7), without blocking the rice (Oryza sativa) SL receptor DWARF14 (OsD14). Moreover, triazole ureas, the potent covalently binding antagonists of rice SL perception with much higher activity toward OsD14, showed inhibition of Striga but were less specific. Considering that Triton X-100 is not suitable for field application and by combining structural elements of Triton and triazole urea, we developed two hybrid compounds, KK023-N1 and KK023-N2, as potential Striga-specific germination inhibitors. Both compounds blocked the hydrolysis activity of ShHTL7 but did not affect that of OsD14. Binding of KK023-N1 diminished ShHTL7 interaction with S. hermonthica MORE AXILLARY BRANCHING 2, a major component in SL signal transduction, and increased ShHTL7 thermal specificity. Docking studies indicate that KK023-N1 binding is not covalent but is caused by hydrophobic interactions. Finally, in vitro and greenhouse tests revealed specific inhibition of Striga seed germination, which led to a 38% reduction in Striga infestation in pot experiments. These findings reveal that KK023-N1 is a potential candidate for combating Striga and a promising basis for rational design and development of further Striga-specific herbicides.


Asunto(s)
Grano Comestible/parasitología , Germinación/efectos de los fármacos , Reguladores del Crecimiento de las Plantas , Malezas/efectos de los fármacos , Malezas/crecimiento & desarrollo , Semillas/crecimiento & desarrollo , Striga/efectos de los fármacos , Striga/crecimiento & desarrollo , Agentes de Control Biológico , Productos Agrícolas/parasitología , Semillas/efectos de los fármacos , Control de Malezas/métodos
18.
Molecules ; 26(21)2021 Nov 08.
Artículo en Inglés | MEDLINE | ID: mdl-34771155

RESUMEN

The phytotoxicity and eco-compatibility of essential oils (EOs) from Eucalyptus gunnii (EG) and E. pulverulenta 'Baby Blue' (EP), cultivated in Italy for their cut foliage, were investigated. Leaf micromorphology, EOs phytochemical characterization, and phytotoxicity were analysed. EP revealed a significantly higher oil gland density and a higher EO yield with respect to EG. In both EOs, 1,8-cineole was the major compound (~75%), followed by α-pinene in EG (13.1%) and eugenol in EP (7.5%). EO phytotoxicity was tested on both weeds (Lolium multiflorum, Portulaca oleracea) and crops (Raphanus sativus, Lactuca sativa, Lepidium sativum, Solanum lycopersicum, Pisum sativum, Cucumis sativus). EG EO inhibited germination of P. oleracea, R. sativus, and S. lycopersicum seeds (ranging from 61.5 to 94.6% for the higher dose used), while affecting only radical elongation in S. lycopersicum (ranging from 66.7 to 82.6%). EP EO inhibited germination of P. oleracea and R. sativus (ranging from 41.3 to 74.7%) and affected radical elongation of L. sativum and L. multiflorum (ranging from 57.4 to 76.0%). None of the EOs affected the germination and radical growing of L. sativa, P. sativum, and C. sativus. Moreover, EP EO was more active than EG EO in inhibiting α-amylase, a key enzyme for seed growth regulation. Brine shrimp lethality assay showed that both EOs are safe for aquatic organisms, suggesting their high eco-compatibility. The data collected provide useful information for future applications of these EOs in agriculture as safe and selective bioherbicides.


Asunto(s)
Productos Agrícolas/efectos de los fármacos , Eucalyptus/química , Herbicidas/farmacología , Aceites Volátiles/farmacología , Fitoquímicos/farmacología , Malezas/efectos de los fármacos , Animales , Artemia , Germinación/efectos de los fármacos , Herbicidas/química , Herbicidas/aislamiento & purificación , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación
19.
Pak J Biol Sci ; 24(9): 989-996, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34585552

RESUMEN

<b>Background and Objective:</b> Boron is one of the principal elements required for plant's growth but extreme amounts of boron are toxic to humans, animals and plants. This study aimed to utilized growth rates, dry biomass and antioxidant enzyme activities to evaluate the potential of <i>Spirodela polyrhiza</i> L., in which <i>S. polyrhiza</i> produced for 120 hrs in water containing control, 10, 20, 40 and 80 mg L<sup>1</sup> of Boron and sodium chloride (NaCl) concentrations changing from 0-50 mM. <b>Materials and Methods:</b> In this study, we have done with <i>S. polyrhiza</i>, Boron and NaCl applications were continued for 120 hrs. After 120 hrs, the plants were harvested, cleaned with pure water, frozen at fluid nitrogen and stored at -80°C until further usage for enzymes activity. To determine the amount of Boron in <i>S. polyrhiza</i>, the samples were dried at 70 and then measured with Thermo ICP-MS. <b>Results:</b> The results indicated that the Boron accumulation capacity of <i>S. polyrhiza</i> diminished with accelerating salinity. <i>Spirodela polyrhiza</i> may have utilized various mechanisms to collecting Boron in high and low salt concentrations. As a conclusion of the study, it was stated that the growth rate of <i>S. polyrhiza</i> and total chlorophyll synthesis were considerably obstructed when NaCl amounts reached 50 mM. <b>Conclusion:</b> Our results indicate that CAT, APX and SOD can serve as substantial biomarkers in Boron-rich habitats. This <i>S. polyrhiza</i> is a very beneficial exemplary plant for phytoremediation advancement of contaminated wastewater with low Boron content.


Asunto(s)
Antioxidantes/metabolismo , Boro/farmacología , Malezas/efectos de los fármacos , Cloruro de Sodio/farmacología , Antioxidantes/fisiología , Boro/efectos adversos , Cloruro de Sodio/efectos adversos
20.
Mol Plant ; 14(12): 2115-2125, 2021 12 06.
Artículo en Inglés | MEDLINE | ID: mdl-34509639

RESUMEN

In modern agriculture, frequent application of herbicides may induce the evolution of resistance in plants, but the mechanisms underlying herbicide resistance remain largely unexplored. Here, we report the characterization of rtp1 (resistant to paraquat 1), an Arabidopsis mutant showing strong resistance to the widely used herbicides paraquat and diquat. The rtp1 mutant is semi-dominant and carries a point mutation in the gene encoding the multidrug and toxic compound extrusion family protein DTX6, leading to the change of glycine to glutamic acid at residue 311 (G311E). The wild-type DTX6 with glycine 311 conferred weak paraquat and diquat resistance when overexpressed, while mutation of glycine 311 to a negatively charged amino acid (G311E or G311D) markedly increased the paraquat and diquat resistance of plants, whereas mutation to a positively charged amino acid (G311R or G311K) compromised the resistance, suggesting that the charge property of residue 311 of DTX6 is critical for the paraquat and diquat resistance of Arabidopsis plants. DTX6 is localized in the endomembrane trafficking system and may undergo the endosomal sorting to localize to the vacuole and plasma membrane. Treatment with the V-ATPase inhibitor ConA reduced the paraquat resistance of the rtp1 mutant. Paraquat release and uptake assays demonstrated that DTX6 is involved in both exocytosis and vacuolar sequestration of paraquat. DTX6 and DTX5 show functional redundancy as the dtx5 dtx6 double mutant but not the dtx6 single mutant plants were more sensitive to paraquat and diquat than the wild-type plants. Collectively, our work reveals a potential mechanism for the evolution of herbicide resistance in weeds and provides a promising gene for the manipulation of plant herbicide resistance.


Asunto(s)
Aminoácidos Acídicos/metabolismo , Arabidopsis/genética , Dihidropiridinas/toxicidad , Resistencia a los Herbicidas , Mutación/genética , Paraquat/toxicidad , Arabidopsis/efectos de los fármacos , Regulación de la Expresión Génica de las Plantas/efectos de los fármacos , Hojas de la Planta/efectos de los fármacos , Hojas de la Planta/genética , Hojas de la Planta/metabolismo , Raíces de Plantas/efectos de los fármacos , Raíces de Plantas/genética , Raíces de Plantas/metabolismo , Malezas/efectos de los fármacos
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