Growth inhibition of sourgrass as a function of period of darkness after diquat application

Photosystem-inhibiting herbicides, such as diquat, act by inducing oxidative stress. However, oxidative damage impairs translocation, resulting in regrowth of the plants. The aim was to evaluate the effectiveness of diquat in controlling the growth of sourgrass exposed to different periods of darkness after application of the herbicide, as well as to evaluate the photosynthetic activity and the production of reactive oxygen species. Two experiments (field and greenhouse) were conducted by applying diquat (200 g a.i. ha-1) on sourgrass plants at the 3 to 4 tiller stage. The treated plants were subjected to different periods of darkness after diquat application (0, 1, 2, 3, 4, 5, and 6 h), in addition to the control treatment without any application. Growth inhibition and mass evaluations of the sourgrass plants were performed in both experiments, whereas photosynthetic activity and H2O2 accumulation in the leaves were evaluated in the greenhouse experiment. The results showed an increase in the sourgrass growth inhibition with an increase in the period of darkness after application. There was a need for a minimum of 6 h of darkness after diquat application to fully inhibit growth (100%) of the sourgrass, whereas plants that remained in the sun since application exhibited less than 50% inhibition. The increase in the period of darkness after diquat application resulted in a reduction in photosynthetic activity and, consequently, lower accumulation of H2O2. Thus, the maintenance of sourgrass in the dark for at least 6 h enables total control of the growth of the plants, preventing regrowth.

ß-Resorcylic Acid Derivatives, with Their Phytotoxic Activities, from the Endophytic Fungus Lasiodiplodia theobromae in the Mangrove Plant Xylocarpus granatum.

Nine new ß-resorcylic acid derivatives, (15S)-de-O-methyllasiodiplodin (1), (13S,15S)-13-hydroxy-de-O-methyllasiodiplodin (2), (14S,15S)-14-hydroxy-de-O-methyllasiodiplodin (3), (13R,14S,15S)-13,14-dihydroxy-de-O-methyllasiodiplodin (4), ethyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (5), ethyl 2,4-dihydroxy-6-(8-hydroxyheptyl)benzoate (6), ethyl 2,4-dihydroxy-6-(4-methoxycarbonylbutyl)benzoate (7), 3-(2-ethoxycarbonyl-3,5-dihydroxyphenyl)propionic acid (8), and isobutyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (9), together with a known ethyl 2,4-dihydroxy-6-(8-oxononyl)benzoate (10) were obtained from Lasiodiplodia theobromae GC-22. The structures of these compounds were elucidated by extensive spectroscopic analyses. Compounds 1, 3, and 6 showed growth inhibitory effects against Digitaria ciliaris. Conversely, treatment with compounds 5, 6, 7, 9, and 10 stimulated elongation activity toward the root of Lactuca sativa. These data expand the repertoire of new ß-resorcylic acid derivatives that may function as lead compounds in the synthesis of new agrochemical agents.

Herbicidal Characteristics and Structural Identification of the Potential Active Compounds from Streptomyces sp. KRA17-580.

Weeds are notorious plant species exhibiting a harmful impact on crops. Biological weed control is an efficient and environmentally friendly technique, usually constitutes naturally derived compounds, including bioherbicidal metabolites produced by Streptomyces sp. The isolation and structural identification of phytotoxic compounds from Streptomyces have recently been proposed as an effective way to the discovery of novel bioherbicides. In the screening of bioherbicidal agents, isolated Streptomyces strain KRA17-580 demonstrated significant phytotoxic activity against Digitaria ciliaris. Phylogenetic analysis of the 16S rRNA sequence indicated that isolated KRA17-580 is similar to Streptomyces olivochromogenes. The bacterial culture conditions were optimized for temperature, agitation, and initial pH. Streptomyces strain KRA17-580 showed intense phytotoxic activity and high cell mass at an initial pH of 5.5-7.0, more than 150 rpm, and 25-30 °C. The herbicidal compounds isolated from the culture filtrate of strain KRA17-580 were purified by solvent partition, C18, Sephadex LH20 column chromatography, and high-performance liquid chromatography. By 1D-NMR, 2D-NMR, and electrospray ionization mass spectrometry analysis, the 580-H1 and 580-H2 compounds were identified as a cinnoline-4-carboxamide (MW, 173.0490; C9H7N3O2) and cinnoline-4-carboxylic acid (MW, 174.0503; C9H6N2O2), respectively. Only these two herbicidal compounds showed strong phytotoxic activity against D. ciliaris in foliar applications. However, compound 580-H2 was more phytotoxic than 580-H1 and the toxicity was dose-dependent. The herbicidal metabolite KRA17-580 produced by Streptomyces sp. is a new bioherbicidal candidate that may provide a new lead molecule for more efficient phytotoxic compounds.

Synthesis of Pyranopyrans Related to Diplopyrone and Evaluation as Antibacterials and Herbicides.

Stereoselective syntheses of new pyranopyrans that are related to the natural product diplopyrone, which is a phytotoxin implicated in cork oak decline, have been achieved from carbohydrate starting materials in two approaches that are based on C-glycosides as key intermediates. A C-alkynyl glycoside prepared by Ferrier rearrangement was used as the precursor to a new pyranopyran alkyne that showed potent antibacterial activity against the common bacterial pathogen Edwardsiella ictaluri that causes enteric septicemia in catfish. The C-alkynyl glycoside also showed herbicidal activity. New bioassay data for the pyranopyran nitrile (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one, the most potent of the pyranopyrans synthesized to date, were obtained in greenhouse studies that revealed additional herbicidal activity. Other new analogues that were synthesized included desmethylpyranopyrans that were prepared by Isobe C-alkynylation-rearrangement/reduction and RCM-based pyranopyran construction. The antibiotic and phytotoxic activities of the new pyranopyrans synthesized in this study highlight the importance of substituents on the nonlactone ring and demonstrate the potential of such compounds as antibiotics and herbicides.

Cytisus scoparius and Ulex europaeus Produce Volatile Organic Compounds with Powerful Synergistic Herbicidal Effects.

New herbicides based on natural products are claimed to address weed resistance and environmental concerns related to synthetic herbicides. In our previous studies, certain volatile organic compounds (VOCs) produced by Ulex europaeus and Cytisus scoparius were argued to be responsible for the phytotoxicity of both shrub species. Interactions among VOCs were hypothesized to explain the inconsistency between the effects of the identified pure compounds and those naturally emitted from fresh plant material. In this work, eugenol, verbenone, terpinen-4-ol, α-terpineol, and linalool were assayed as binary mixtures of Amaranthus retroflexus and Digitaria sanguinalis. Powerful synergistic inhibitory effects were revealed for germination and early growth. Only 3.1 ppm of verbenone was enough to inhibit A. retroflexus germination when paired to other VOCs. Eugenol was capable of exacerbating the effects of terpinen-4-ol on A. retroflexus, even though it was innocuous when acting alone at 12.5 ppm. The verbenone and linalool pair produced very significant synergistic effects in terms of D. sanguinalis germination. The synergistic effects were predominantly irreversible for D. sanguinalis, since seeds exposed to paired VOCs were unable to recover their germination capacity after removing the phytotoxins or produced damaged seedlings. Both shrub species have been revealed as sources of natural herbicide molecules, with promising synergistic modes of action that deserve to be studied in depth.

On the bioherbicide potential of Ulex europaeus and Cytisus scoparius: Profiles of volatile organic compounds and their phytotoxic effects.

The phytotoxic potential of the legume shrubs Ulex europaeus L. (gorse) and Cytisus scoparius (L.) Link. (Scotch broom) is studied in this work for the first time. On the basis of their richness in active principles, the previous evidence of biological activity, and the abundance of biomass in their native range and invaded areas, a question arose: can U. europaeus and C. scoparius be considered as potential sources of natural herbicides for sustainable agriculture? By means of volatile bioassays, the flowering fresh plant material of both shrub species was shown to produce and emit volatile organic compounds (VOCs) able to inhibit the germination and/or early growth of two agricultural weeds: Amaranthus retroflexus and Digitaria sanguinalis. Novel complete VOCs profiles from the volatile extracts of the shrub species were obtained by GC and GC/MS. A total of 20 compounds were identified from U. europaeus flowering biomass, theaspirane and eugenol, among others, being described in gorse for the first instance. The chemical profile of C. scoparius yielded 28 compounds and was rich in oxygenated monoterpenes such as terpinen-4-ol, verbenol, α-terpineol, and verbenone, which were also identified in this species for the first time. Using dose-response bioassays with pure compounds, these VOCs were argued to be involved in the phytotoxicity observed for the plant materials, even at very low concentrations. The phytotoxic effects were predominantly irreversible, particularly for D. sanguinalis, since the seeds exposed to the VOCs produced damaged seedlings, were unable to recover germination capacity after removing the phytotoxin or, when recovered, produced unviable seedlings. Our results extend the interest of the abundant U. europaeus and C. scoparius for the obtention of natural products with bioherbicide potential, or to be used as allelopathic biomass in the development of new sustainable agricultural practices.

Bioactive Resorcylic Acid Lactones with Different Ring Systems from Desert Plant Chaetosphaeronema hispidulum. [corrected].

Five new resorcylic acid lactones (RALs) hispidulactones A-E (1, 4, 5, 8, and 9), a new natural product (2), and four known ones (3, 6, 7, and 10) with different ring systems were isolated from the desert plant Chaetosphaeronema hispidulum. [corrected]. The new compounds were characterized by NMR data, CD spectra, and X-ray experiment. The new natural product (2) displayed strongly biological effects on the seedlings growth of Arabidopsis thaliana, Digitaria sanguinalis, and Echinochloa crusgalli with a dose-dependent relationship. Compounds 1, 2, and 6 were also tested cytotoxic activities against three cancer cell lines HCT116, Hela, and MCF7 and only did the new natural product (2) display biological activities with IC50 values at 54.86 ± 1.52, 4. 90 ± 0.02, and 20.04 ± 4.00 µM, respectively, whereas the IC50 values of the positive control cis-platinum were 11.36 ± 0.42, 3.54 ± 0.12, and 14.32 ± 1.01 µM, respectively.

Soil heavy metal contamination and health risks associated with artisanal gold mining in Tongguan, Shaanxi, China.

Soil contamination with heavy metals due to mining activities poses risks to ecological safety and human well-being. Limited studies have investigated heavy metal pollution due to artisanal mining. The present study focused on soil contamination and the health risk in villages in China with historical artisanal mining activities. Heavy metal levels in soils, tailings, cereal and vegetable crops were analyzed and health risk assessed. Additionally, a botany investigation was conducted to identify potential plants for further phytoremediation. The results showed that soils were highly contaminated by residual tailings and previous mining activities. Hg and Cd were the main pollutants in soils. The Hg and Pb concentrations in grains and some vegetables exceeded tolerance limits. Moreover, heavy metal contents in wheat grains were higher than those in maize grains, and leafy vegetables had high concentrations of metals. Ingestion of local grain-based food was the main sources of Hg, Cd, and Pb intake. Local residents had high chronic risks due to the intake of Hg and Pb, while their carcinogenic risk associated with Cd through inhalation was low. Three plants (Erigeron canadensis L., Digitaria ciliaris (Retz.) Koel., and Solanum nigrum L.) were identified as suitable species for phytoremediation.

The disposal of a lime water treatment residue on soil and spoil material from a coalmine: a glasshouse investigation.

Eragrostis tef (Zucc.), Cenchrus ciliaris L., and Digitaria eriantha Steud. were grown in a soil (Psammentic Haplustalf) and spoil material from a coalmine both treated with a lime water treatment residue (WTR) at rates of 0, 50, 100, 200, and 400 g kg(-1). The yield of the grasses, from the sum of the three harvests, and concentrations of B, Ca, Cu, K, Fe, Mg, Mn, N, Na, P, and Zn in foliage from the second harvest were determined. The yield of grasses grown in the soil decreased exponentially as WTR application increased. The yields of C. ciliaris, D. eriantha, and E. tef (in the 400 g kg(-1) WTR treated soil) decreased by 74.4, 78.7, and 59.8%, respectively, when compared with the control treatments. In the spoil, the yield of E. tef and D. eriantha decreased by 13.6% and and D. eriantha by 23.9%, while an increase was observed for C. ciliaris (45.4%), at the highest WTR application rate. No relationship existed between yield of E. tef and WTR application rate when grown in the spoil, while a weak negative linear relationship (p < 0.05) was found for D. eriantha and a positive linear relationship existed for C. ciliaris. Magnesium concentrations of the grasses were positively correlated to WTR application rate. Grasses grown in the soil had higher Na concentrations, while those grown in the spoil typically had higher B, N, and Zn concentrations. The decreases in yield were attributed to nutrient deficiencies (notably Zn), induced by high WTR application rates that led to high substrate pH. Disposal of high rates of WTR on the mine materials was not recommended.

Effect of crabgrass (Digitaria ciliaris) hay harvest interval on forage quality and performance of growing calves fed mixed diets.

Twelve 0.81-ha crabgrass (Digitaria ciliaris [Retz.] Koel.) hay fields were harvested at 21, 35, and 49 d of regrowth (average phonological growth stage of 30, 51, and 56, respectively). Increased harvest interval exhibited a linear decrease (P < 0.01) in CP (14.1, 13.7, and 10.6% of DM, respectively) and increase (P < 0.01) in NDF (65.3, 70.6, and 70.2% of DM, respectively) and ADF (35.7, 38.9, and 42.7% of DM, respectively). Hays were incorporated into 3 diets that contained 20% (DM basis) crabgrass hay, ground corn (33%), and soybean hulls (32%). Diets contained 14.4, 14.4, and 13.6% CP; 1.83, 1.72, and 1.81 Mcal of NE(m)/kg; and 1.21, 1.10, and 1.17 Mcal of NE(g)/kg; respectively. Diets were fed to beef calves in 12 pens at a rate of 2.3% (DM basis) of BW in 1 experiment (n = 120, initial BW 210 +/- 4.4 kg) and ad libitum in another experiment (n = 60, initial BW 207 +/- 4.4 kg). To measure passage rate of the hay and concentrate portions of the diets, 12 heifer calves (BW = 145 +/- 4.5 kg) were individually fed at 2.3% of BW for 14 d and dosed with Dy-labeled soybean hulls and Yb-labeled hay. In situ DM digestibility of the hays and diets were determined using 3 ruminally cannulated steers (BW = 584 +/- 10.4 kg). Harvest interval did not affect (P > or = 0.11) ADG of limit-fed calves during the diet acclimation or growing phases (average 0.32 and 0.80 kg, respectively) or ADG of calves fed ad libitum (average 1.21 kg). Dry matter intake of calves fed ad libitum averaged 7.9 kg/d (3.28% of BW) and was not affected (P > or = 0.22) by harvest interval. Gain:feed was not affected (P > or = 0.20) by harvest interval (0.13 and 0.15 for limit-fed and ad libitum-fed calves, respectively). Increased harvest interval linearly increased (P < 0.01) ruminal retention time of the hay and tended (P = 0.06) to linearly increase ruminal retention time of the concentrate portions of the diet. Harvest interval linearly decreased (P < or = 0.05) the extent of degradability and effective degradability of DM and NDF of hays, but DM disappearance of the total diet did not differ (P > or = 0.35). In the conditions of this study, increasing harvest interval of crabgrass hay from 21 to 49 d had no deleterious impact on animal performance or efficiency of gain when fed to growing calves in a high-concentrate mixture.

Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop.

The objective of this research was to study population dynamics of the weed crabgrass, genus Digitaria, submitted to selection pressure by herbicides currently applied in sugarcane crops in Brazil. In the first experiment two crabgrass species (Digitaria nuda and Digitaria ciliaris) and eight herbicide treatments applied in preemergence were used, and control percentage was evaluated at 7, 14, and 21 days after herbicide application (DAA). In the second experiment the level of tolerance through dose-response curve was determined for the species D. nuda and D. ciliaris, to the herbicides imazapyr, tebuthiuron, ametryne, and metribuzin. All the herbicides studied were efficient in controlling D. ciliaris, however, for D. nuda the best results were obtained only with ametryne, metribuzin, and isoxaflutole. The relation (T/S) between the rate required to reduce plant dry biomass (GR50) at 21 DAA of D. nuda and D. ciliaris was 16 for imazapyr and 6.3 for tebuthiuron, showing differential susceptibility of species; however for ametryne the rate T/S of 1.1 showed that D. nuda was not tolerant to this herbicide. For metribuzin, at 1.92 kg a.i. ha(-1), reduction of dry biomass was 80 and 90% to D. nuda and D. ciliaris, respectively. Even being controlled by metribuzin, D. nuda presented a higher level of tolerance to this herbicide, what was confirmed by the relationship T/S 14.4. As general conclusion of the research, it can be stated that the species D. nuda is more tolerant to ALS inhibiting herbicides and substituted urea, when compared with D. ciliaris; probably, D. nuda was selected by repetitive use of these herbicides.