Effects of soil pH on the growth, soil nutrient composition, and rhizosphere microbiome of Ageratina adenophora.

Ageratina adenophora is an invasive weed species found in many countries. Methods to control the spread of this weed have been largely unsuccessful. Soil pH is the most important soil factor affecting the availability of nutrients for plant and impacting its growth. Understanding the mechanisms of the influence of soil pH on the growth of A. adenophora may help to develop effective control measures. In this study, we artificially changed the soil pH in pot experiments for A. adenophora. We studied the effects of acidic (pH 5.5), weakly acidic (pH 6.5), neutral (pH 7.2), and alkaline (pH 9.0) soils on the growth, availability of soil nutrients, activity of antioxidant enzymes, levels of redox markers in the leaves, and the structure and diversity of the rhizosphere microbiome. Soil with a pH 7.2 had a higher (47.8%) below-ground height versus soils of pH 5.5 at day 10; plant had a higher (11.3%) above-ground height in pH 7.2 soils than pH 9.0 soils at day 90; no differences in the fresh and dry weights of its above- and belowground parts, plant heights, and root lengths were observed in plants growing in acid, alkaline, or neutral pH soil were observed at day 180. Correspondingly, the antioxidant enzymes SOD (superoxide dismutase), POD (peroxidase), CAT (catalase) and redox markers GSH (glutathione) and MDA (malondialdehyde) were measured in the leaves. Significant differences existed in the activities of CAT and the levels of GSH between those growing in acidic and alkaline soils and those in neutral pH soil at day 90; however, only lower (36.8%) CAT activities in those grown at pH 5.5 than those grown at pH 7.2 were found at day 180. Similarly, significant differences in available P (16.89 vs 3.04 mg Kg-1) and total K (3.67 vs 0.96 mg Kg-1), total P (0.37 vs 0.25 g Kg-1) and total N (0.45 vs 1.09 g Kg-1) concentrations were found between the rhizosphere soils of A. adenophora grown at pH 9.0 and 7.2 at day 90; no such differences were seen at day 180. High throughput analyses of the 16S rRNA and ITS fragments showed that the rhizosphere microbiome diversity and composition under different soil pH conditions changed over 180 days. The rhizosphere microbiomes differed in diversity, phylum, and generic composition and population interactions under acid and alkaline conditions versus those grown in neutral soils. Soil pH had a greater impact on the diversity and composition of the prokaryotic rhizosphere communities than those of the fungal communities. A. adenophora responded successfully to pH stress by changing the diversity and composition of the rhizosphere microbiome to maintain a balanced nutrient supply to support its normal growth. The unusual pH tolerance of A. adenophora may be one crucial reason for its successful invasion. Our results suggest that attempts use soil pH to control its invasion by changing the soil pH (for example, using lime) will fail.

Activation Mechanism of Strigolactone Receptors and Its Impact on Ligand Selectivity between Host and Parasitic Plants.

Parasitic weeds such as Striga have led to significant losses in agricultural productivity worldwide. These weeds use the plant hormone strigolactone as a germination stimulant. Strigolactone signaling involves substrate hydrolysis followed by a conformational change of the receptor to a "closed" or "active" state that associates with a signaling partner, MAX2/D3. Crystal structures of active and inactive AtD14 receptors have helped elucidate the structural changes involved in activation. However, the mechanism by which the receptor activates remains unknown. The ligand dependence of AtD14 activation has been disputed by mutagenesis studies showing that enzymatically inactive receptors are able to associate with MAX2 proteins. Furthermore, activation differences between strigolactone receptor in Striga, ShHTL7, and AtD14 could contribute to the high sensitivity to strigolactones exhibited by parasitic plants. Using molecular dynamics simulations, we demonstrate that both AtD14 and ShHTL7 could adopt an active conformation in the absence of ligand. However, ShHTL7 exhibits a higher population in the inactive apo state as compared to the AtD14 receptor. We demonstrate that this difference in inactive state population is caused by sequence differences between their D-loops and interactions with the catalytic histidine that prevent full binding pocket closure in ShHTL7. These results indicate that ligand hydrolysis would enhance the active state population by destabilizing the inactive state in ShHTL7 as compared to AtD14. We also show that the mechanism of activation is more concerted in AtD14 than in ShHTL7 and that the main barrier to activation in ShHTL7 is closing of the binding pocket.

Invasive alien plants and weeds in South Africa: A review of their applications in traditional medicine and potential pharmaceutical properties.

ETHNOPHARMACOLOGICAL RELEVANCE: Traditional pharmacopoeias are constantly evolving and adapting, hence the assimilation of alien plants and weeds into traditional systems of healing. Invasive plants are detrimental to the ecosystem, however they are also potential sources of secondary metabolites with useful biological activities. AIM OF THE REVIEW: The aim of this review was to investigate published reports of traditional use and biological activity of declared invasive alien plants and other weeds in South Africa. MATERIALS AND METHODS: Information was retrieved from scientific databases including Scopus, Web of Science, ScienceDirect, Google Scholar, PubMed, Chemical Abstracts Services and books, theses, dissertations and technical reports. Keywords used for the search engines were "South Africa" or "southern Africa" in conjunction with "(native weeds OR alien invasive)" AND "medicinal". Separate searches were conducted on the individual invasive plant species recorded as having been used in ethnobotanical surveys to determine their known biological activities and chemical components. RESULTS: A total of 89 plant species regarded as invasive species or weeds in South Africa were identified as being used in traditional medicine. The most commonly mentioned plant family was the Asteraceae with a total of 15 species followed by the Fabaceae and Solanaceae with 6 species each. Of the 89 species recorded, 68% were reported to have traditional usage with both phytochemical and biological data available. A history of traditional usage coupled with biological data was available for 12% of species. Records of traditional usage alone were linked to 11% of species. Invasive alien species comprised 61% of recorded species, while native and non-invasive alien weeds formed the remaining 39%. CONCLUSIONS: The exploration of alternative uses for weeds and particularly invasive plants, whether native or alien, as medicines for possible commercialisation may lead to innovative mechanisms for putting such species to good use.

Effective methane production from the Japanese weed Gyougi-shiba (Cynodon dactylon) is accomplished by colocalization of microbial communities that assimilate water-soluble and -insoluble fractions.

Weed, an abundant biomass, is considered unsuitable as a raw material for methane production. There are few reports on the anaerobic digestion of weeds without the addition of other organic wastes. To solve this problem, a methane-producing microbial community with weed as a sole feedstock was established. This study mainly focused on the degree of contribution between water-soluble and -insoluble fractions of the weed to methane production; thus, methane production from both fractions was tested separately. Methane production after 80-day batch cultures with whole weed, water-soluble and water-insoluble fractions was 184.5, 96.8 and 26.5 NmL g-1 dry matter (DM), respectively. The results of 16S rRNA gene amplicon sequence analysis revealed that Proteiniphilum saccharofermentans and several Methanobacterium species commonly dominated all cultures, whereas the population dynamics of minor species differed in every culture. Moreover, the remixed culture of microbial communities adapted to water-soluble and -insoluble fractions recovered methane production (252.4 NmL g-1 DM). Based on these results, it can be strongly inferred that colocalizing the minor species in water-soluble and -insoluble fractions is important for effective methane production.

Chemical composition and phytotoxicity of essential oil from invasive plant, Ambrosia artemisiifolia L.

Essential oils have been evaluated as appropriate phytotoxins with mechanisms of action that are different from those of synthetic herbicides applied in weed management activities, but little is known about the effect of Ambrosia artemisiifolia essential oil (EO) on weeds. Here, the chemical composition of A. artemisiifolia EO was analyzed using a Gas Chromatography-Mass Spectrometry system. and the phytotoxic activities of the EO against monocot (Poa annua, Setaria viridis) and dicot (Amaranthus retroflexus, Medicago sativa) species are evaluated under laboratory and green-house conditions for the first time. The EO was rich in sesquiterpenes (62.51%), with germacrene D (32.92%), ß-pinene (15.14%), limonene (9.90%), and caryophyllene (4.49%) being the major compounds based on Gas Chromatography-Mass Spectrometry analysis results. A. artemisiifolia EO inhibited seed germination and seedling development significantly in the tested species even at low concentrations (0.25 mg mL-1). In addition, bioassay results for the activities of superoxide dismutase (SOD) and peroxidase (POD) increased and then decreased with an increase in EO concentration. Unlike the enzymatic activity, root cell viability declined significantly in the tested weeds in all EO treatments. Besides, a foliar spray experiment resulted in visible injury in leaves and a decrease in chlorophyll content and eventually led to wilting of all tested weeds. The EO (0.25-5.00 mg mL-1) altered Allium cepa root tip cells with a decline in mitotic index and an increase in chromosomal aberrations after 24 h treatment. The cytotoxic evaluation confirmed the mitotic inhibitory effect of EO, although the intensity varied under different concentrations. According to the results, A. artemisiifolia EO has the potential applications as a natural herbicide owing to its phytotoxic activity; which also helps to explain their potential involvement in allelopathic interaction of volatile compounds present in the EO that facilitate the invasion success of the exotic species.

Betacyanins and Betaxanthins in Cultivated Varieties of Beta vulgaris L. Compared to Weed Beets.

There are 11 different varieties of Beta vulgaris L. that are used in the food industry, including sugar beets, beetroots, Swiss chard, and fodder beets. The typical red coloration of their tissues is caused by the indole-derived glycosides known as betalains that were analyzed in hypocotyl extracts by UV/Vis spectrophotometry to determine the content of betacyanins (betanin) and of betaxanthins (vulgaxanthin I) as constituents of the total betalain content. Fields of beet crops use to be also infested by wild beets, hybrids related to B. vulgaris subsp. maritima or B. macrocarpa Guss., which significantly decrease the quality and quantity of sugar beet yield; additionally, these plants produce betalains at an early stage. All tested B. vulgaris varieties could be distinguished from weed beets according to betacyanins, betaxanthins or total betalain content. The highest values of betacyanins were found in beetroots 'Monorubra' (9.69 mg/100 mL) and 'Libero' (8.42 mg/100 mL). Other beet varieties contained less betacyanins: Sugar beet 'Labonita' 0.11 mg/100 mL; Swiss chard 'Lucullus,' 0.09 mg/100 mL; fodder beet 'Monro' 0.15 mg/100 mL. In contrast with weed beets and beetroots, these varieties have a ratio of betacyanins to betaxanthins under 1.0, but the betaxanthin content was higher in beetcrops than in wild beet and can be used as an alternative to non-red varieties. Stability tests of selected varieties showed that storage at 22 °C for 6 h, or at 7 °C for 24 h, did not significantly reduce the betalain content in the samples.

Nutrients Supplementation through Organic Manures Influence the Growth of Weeds and Maize Productivity.

Declining rate of productivity and environmental sustainability is forcing growers to use organic manures as a source of nutrient supplement in maize farming. However, weed is a major constraint to maize production. A field study was carried out over two seasons to evaluate various integrated nutrient and weed management practices in hybrid maize. The treatment combinations comprised of supplementation of inorganic fertilizer (25% nitrogen) through bulky (Farmyard manure and vermicompost) and concentrated (Brassicaceous seed meal (BSM) and neem cake (NC)) organic manures and different mode of weed management practices like chemical (atrazine 1000 g ha-1) and integrated approach (atrazine 1000 g ha-1 followed by mechanical weeding). Repeated supplementation of nitrogen through concentrated organic manures reduced the density and biomass accumulation of most dominant weed species, Anagalis arvensis by releasing allelochemicals into the soil. But organic manures had no significant impact on restricting the growth of bold seeded weeds like Vicia hirsuta and weed propagated through tubers i.e., Cyperus rotundus in maize. By restricting the weed growth and nutrient removal by most dominating weeds, application of BSM enhanced the growth and yield of maize crop. Repeated addition of organic manures (BSM) enhanced the maize grain yield by 19% over sole chemical fertilizer in the second year of study. Application of atrazine as pre-emergence (PRE) herbicide significantly reduced the density of A. arvensis, whereas integration of mechanical weeding following herbicide controlled those weeds which were not usually controlled with the application of atrazine. As a result, atrazine at PRE followed by mechanical weeding produced the highest maize grain yield 6.81 and 7.10 t/ha in the first year and second year of study, respectively.

Comparative Studies of Potential Binding Pocket Residues Reveal the Molecular Basis of ShHTL Receptors in the Perception of GR24 in Striga.

Root parasitic weeds such as Striga spp. have caused significant losses in agriculture production worldwide. The seed germination of the weeds depends on strigolactones (SLs) that target a series of HYPOSENSITIVE TO LIGHT/KARRIKIN INSENSITIVE2 in Striga hermonthica (ShHTL) proteins. In the present study, 60 ShHTL7 mutants were constructed, and the equilibrium dissociation constants for GR24 (a synthetic SL analogue, commonly used as a standard in SL germination studies) against these mutants were measured by surface plasmon resonance. Based on these data, the SL binding pocket residues were distinguished. Of them, some specific residues for ShHTL7 were found, such as T142, T190, and M219. A model showing quite well internal and external predictive abilities was established by the mutation-dependent biomacromolecular quantitative structure-activity relationship method. It provided an expanded understanding for GR24 binding to a series of ShHTL receptors and should help design broad-spectrum agrochemicals with cross interactions with several members of SL receptors.

Investigating the use of aquatic weeds as biopesticides towards promoting sustainable agriculture.

Aquatic weeds such as muskgrass (Chara spp.), water hyacinth (Eichhornia crassipes), water lettuce (Pistia stratiotes), hydrilla (Hydrilla verticillate), filamentous algae (Lyngbya wollei), and duckweed (Lemna minor) thrive in farm canals within the Everglades Agricultural Area of South Florida. Their presence, particularly during the summer months is an environmental concern with regards to water quality, in addition to being a nuisance because of their ability to multiply and spread rapidly in open waters causing restricted drainage/irrigation flow and low dissolved oxygen levels. Chemical control is effective but can have undesirable off-target effects, so reduced herbicide use is desirable. Hence, need exists to discover ways in which these weeds could be best managed or utilized. The objective of this research was to evaluate the allelopathic effect of these weeds to determine their use as potential biopesticides. Six aqueous extracts were tested against 100 bacterial strains isolated from plants and soil to evaluate their antimicrobial activity. These extracts were also used to determine their insecticidal and antifeedant effects on fall armyworm (FAW, Spodoptera frugiperda). Both extracts and powder form of the aquatic weeds were tested for their herbicidal activity towards seed germination and growth of three common terrestrial weed species. At a dilution of 1:100 and 1:1,000, none of the aquatic weeds inhibited in-vitro growth of the bacterial strains, with one exception (filamentous algae extract at 1:100 reduced growth of one bacterial isolate by 54%). Water lettuce reduced the survival rate of FAW by 14% while hydrilla and duckweed caused 11% and 9% reduction of FAW growth, respectively. Powdered duckweed inhibited the growth of nutsedge by 41%, whereas filamentous algae powder and extract reduced germination of amaranth by 20% and 28%, respectively. Harvesting these weeds and converting them into useable compounds could not only eliminate the in situ farm canal and water quality problems but also result in development of new soil amendments or biopesticides.

Comparison of allelopathic effects of two typical invasive plants: Mikania micrantha and Ipomoea cairica in Hainan island.

Mikania micrantha and Ipomoea cairica are two invasive plants widely distribute and seriously damage in Hainan island. In this study, the leaves extracts of two weeds were collected and determined for their allelopathic potentials on Chrysanthemum coronarium. The phytotoxicity bioassay showed that when the extract concentration was 50 and 100 mg/ml, the inhibited effects of M. micrantha on growth of C. coronarium were greater than by I. cairica. However, when the extract concertation at 400 mg/ml, the opposite inhibited effects were observed. We speculated this phenomenon was caused by different allelopathic compounds. Therefore, using gas chromatography-mass spectrometry, 19 and 23 compounds were identified respectively, benzoic acid and cinnamic acid were the main components in the two leaves extracts, which were selected to carry out the further bioassays. Subsequent bioassay results showed the effects of two allelochemicals on morphological index and chlorophyll content and POD activity were all negative to C. coronarium, whereas the content of MDA and activity of SOD, CAT represented adverse changes. Moreover, the inhibitions by cinnamic acid were generally greater than those by benzoic acid. Thus, the phenolic acids played the most crucial roles in the allelopathic effccts of M. micrantha and I. cairica leaves extracts.

Phytochemical composition analysis and evaluation of in vitro medicinal properties and cytotoxicity of five wild weeds: A comparative study.

Background: Medicinal plants are a source of phytochemicals and they are used for the treatment of several oxidative stress-related or other diseases for their effectiveness, low toxicity and easy availability. Five traditionally used and less characterized herbaceous weeds of West Bengal, India, namely, Heliotropium indicum, Tridax procumbens, Cleome rutidosperma, Commelina benghalensis and Euphorbia hirta, were investigated for the current research study. Methods: Aqueous and 70% ethanolic extracts of the leaves were analyzed for estimation of essential phytochemicals and to evaluate their in vitro antioxidant status, medicinal properties and cytotoxic effects. To the best of our knowledge, several assays and comparative evaluations using these herbs are reported for the first time. For quantitative study, UV-vis spectrophotometry and high-performance liquid chromatography with diode array detector HPLC-DAD techniques were used. Antibacterial properties were investigated using the Kirby-Bauer disc diffusion method. For in vitro anti-lithiatic study, a titration method was used. The cell viability assay was done using peripheral blood mononuclear cells. Results: The aqueous extract exhibits higher content of polyphenols, flavonoids, tannins and inhibition percentage values for free radical scavenging assays, whereas the 70% ethanolic extract exhibits higher content of alkaloids and cardiac glycosides. HPLC-DAD analysis of 70% ethanolic extracts led us to identify 10 predominant phenolic constituents. Euphorbia hirta extracts showed minimum cytotoxicity (cell death ~2.5% and 4% in water and 70% ethanolic extract, respectively ), whereas Cleome rutidosperma and Tridax procumbens' 70% ethanolic extracts showed higher cell death (~13% and 28%, respectively), compared with the control (cell death ~10-12%). Conclusions: The study concluded that of all the medicinal weeds selected for the current study, Euphorbia hirta possesses the highest amount of bioactive compounds and hence exhibits the highest in vitro antioxidant activity and promising in vitro medicinal properties.

Insecticidal and Genotoxic effects of some indigenous plant extracts in Culex quinquefasciatus Say Mosquitoes.

Five different weed plants viz. Convulvulus arvensis, Chenopodium murale, Tribulus terrestris, Trianthema portulacastrum, and Achyranthes aspera were investigated for their entomocidal and genotoxic effects against Culex quinquefasciatus mosquitoes. High mortality was observed at 72 hours in a dose dependent manner. Among all the tested plants, A. aspera was found highly significant which showed 100% mortality at 250 ppm after 72 hours with LC50 of 87.46, 39.08 and 9.22 ppm at 24, 48, respectively. In combination with Bacillus thuringiensis israelensis (Bti); A. aspera also caused 100% mortality at 250 ppm concentration after 72 hours (LC50 8.29 ppm). Phytochemical analysis of all the tested weed plants showed the presence of flavonoids, saponins, tannins, steroids, cardiac glycosides, alkaloids, anthrequinones and terpenoids. Random Amplification of Polymorphic DNA-Polymerase chain reaction (RAPD-PCR) and comet assay were performed to assess the genotoxic effect of A. aspera but no change in DNA profile was observed. Furthermore, FTIR showed the presence of phenolic compounds in A. aspera extract. It is suggested that certain phenolic compounds such as flavonoids modulate the enzymatic activity and, hence, cause the death of larvae of Cx. quinquefasciatus. Altogether, current study would serve as an initial step towards replacement of synthetic insecticides to plant-microbe based biopesticide against Culex mosquitoes in future.

Discovery of Novel Pyrazole-Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors.

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been identified as one of the most significant targets in herbicide discovery for resistant weed control. In a continuing effort to discover potent novel HPPD inhibitors, we adopted a ring-expansion strategy to design a series of novel pyrazole-quinazoline-2,4-dione hybrids based on the previously discovered pyrazole-isoindoline-1,3-dione scaffold. One compound, 3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,5-dimethylquinazoline-2,4(1H,3H)-dione (9bj), displayed excellent potency against AtHPPD, with an IC50 value of 84 nM, which is approximately 16-fold more potent than pyrasulfotole (IC50 = 1359 nM) and 2.7-fold more potent than mesotrione (IC50 = 226 nM). Furthermore, the co-crystal structure of the AtHPPD-9bj complex (PDB ID 6LGT) was determined at a resolution of 1.75 Å. Similar to the existing HPPD inhibitors, compound 9bj formed a bidentate chelating interaction with the metal ion and a π-π stacking interaction with Phe381 and Phe424. In contrast, o-chlorophenyl at the N3 position of quinazoline-2,4-dione with a double conformation was surrounded by hydrophobic residues (Met335, Leu368, Leu427, Phe424, Phe392, and Phe381). Remarkably, the greenhouse assay indicated that most compounds displayed excellent herbicidal activity (complete inhibition) against at least one of the tested weeds at the application rate of 150 g of active ingredient (ai)/ha. Most promisingly, compounds 9aj and 9bi not only exhibited prominent weed control effects with a broad spectrum but also showed very good crop safety to cotton, peanuts, and corn at the dose of 150 g of ai/ha.

Edible weeds: Are urban environments fit for foraging?

Foraging wild-growing edible plants (WEPs) is a re-emerging practice with increasing popularity worldwide, including in urban areas. However, in cities, this practice raises questions about the safety of foraging these plants for human consumption, due to the potential exposure of plants to higher levels of pollutants. In this study, the concentration of 12 elements (Al, V, Cr, Mn, Co, Ni, Zn, As, Rb, Cd, Ba and Pb) in three different WEPs (Amaranthus spp., Plantago tomentosa and Taraxacum officinale) were determined according to different traffic categories in the municipality of São Paulo. Additionally, plants were sampled within the inner areas of three municipal parks in the same study region. Different gradients of elemental concentrations were obtained according to the traffic categories. Freeways presented higher concentrations of several elements than local roads or parks. For the WEPs collected along freeways and some plants along arterial roads, the concentrations of Pb exceeded safety levels for human consumption. Our data suggest that foraging in large urban centres should be performed preferentially in low-traffic areas.

Secondary Metabolites from Solanum rostratum and Their Antifeedant Defense Mechanisms against Helicoverpa armigera.

Solanum rostratum is a worldwide malignant invasive weed, causing serious harm to the ecological environment and biodiversity. Strong chemical defense against herbivorous insects is supposed to be one of the successful invasive mechanisms of this exotic plant. However, the real defense components and their action mechanisms and distributions are still unknown. To address these problems, we bioassay-guided isolated compounds from the aerial part of S. rostratum and determined their structures using high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance, and electronic circular dichroism calculation. One new and seven known compounds were identified, and all of the isolates exhibited different levels of antifeedant activities, especially compounds 1 and 4. Consistently, compounds 1 and 4 displayed potent inhibitory effects on antifeedant-related enzymes (AchE and CarE). The action mechanisms of active compounds 1 and 4 were revealed by molecular docking and molecular dynamic simulation studies. Furthermore, the distributions of the active compounds in leaves, stems, and flowers were also analyzed by liquid chromatography-mass spectrometry.

Discovery of Novel N-Isoxazolinylphenyltriazinones as Promising Protoporphyrinogen IX Oxidase Inhibitors.

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a promising target for herbicide discovery. Search for new compounds with novel chemotypes is a key objective for agrochemists. Here, we describe the discovery and systematic SAR-based structure optimization of novel N-isoxazolinylphenyltriazinones 5-9 as PPO inhibitors. The in vivo herbicidal activity and in vitro Nicotiana tabacum PPO (NtPPO) inhibitory activity were explored in detail. A number of the new synthetic compounds displayed strong PPO inhibitory activity with Ki values in the nanomolar range. Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375-37.5 g ai/ha by postemergence application and showed improved monocotyledonous weed control compared to saflufenacil. Most promisingly, ethyl 3-(2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 5a, with a Ki value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (Ki = 10 nM) and trifludimoxazin (Ki = 31 nM), respectively. Moreover, 5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5-75 g ai/ha. Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application, indicating that 5a could be a potential herbicide candidate for weed control in paddy fields.

Easy Access to Alkoxy, Amino, Carbamoyl, Hydroxy, and Thiol Derivatives of Sesquiterpene Lactones and Evaluation of Their Bioactivity on Parasitic Weeds.

It has been hypothesized that the α-methylene-γ-lactone moiety of sesquiterpene lactones is a key unit for their bioactivity. As a consequence, modifications of these compounds have been focused on this fragment. In the work reported here, two sesquiterpene lactones, namely, dehydrocostuslactone and ß-cyclocostunolide, a eudesmanolide obtained by controlled cyclization of costunolide, were chosen for modification by Michael addition at C-13. On applying this reaction to both compounds, it was possible to introduce the functional groups alkoxy, amino, carbamoyl, hydroxy, and thiol to give products in good to high yields, depending on the base and solvent employed. In particular, the introduction of a thiol group at C-13 in both compounds was achieved with outstanding yields (>90%) and this is unprecedented for these sesquiterpene lactones. The bioactivities of the products were evaluated on etiolated wheat coleoptile elongation and germination of seeds of parasitic weeds, with significant activity observed on Orobanche cumana and Phelipanche ramosa. The structure-activity relationships are discussed.

Heavy Metals Bioindication Potential of the Common Weeds Senecio vulgaris L., Polygonum aviculare L. and Poa annua L.

In recent years, heavy metals (HMs) levels in soil and vegetation have increased considerably due to traffic pollution. These pollutants can be taken up from the soil through the root system. The ability of plants to accumulate HMs into their tissues can therefore be used to monitor soil pollution. The aim of this study was to test the ruderal species Senecio vulgaris L., Polygonum aviculare L., and Poa annua L., as possible candidates for biomonitoring Cu, Zn, Cd, Cr, Ni and Pb in multiple environments. The soils analyzed in this work came from three different environments (urban, woodland, and ultramafic), and therefore deeply differed for their metal content, texture, pH, and organic matter (OM) content. All urban soils were characterized by high OM content and presence of anthropogenic metals like Pb, Zn, Cd, and Cu. Woodland soils were sandy and characterized by low metal content and low OM content, and ultramafic soils had high Ni and Cr content. This soil variability affected the bioindication properties of the three studied species, leading to the exclusion of most metals (Zn, Cu, Cr, Cd, and Pb) and one species (P. aviculare) due to the lack of linear relations between metal in soil and metal in plants. Senecio vulgaris and Poa annua, conversely, appeared to be good indicators of Ni in all the soils tested. A high linear correlation between total Ni in soil and Ni concentration in P. annua shoots (R2 = 0.78) was found and similar results were achieved for S. vulgaris (R2 = 0.88).

Biological activity of Dittrichia viscosa (L.) Greuter extracts against adult Sitophilus granarius (L.) (Coleoptera, Curculionidae) and identification of active compounds.

Dittrichia viscosa (L.) Greuter, a perennial weed of the Mediterranean area, was reported to be source of active substances. Here, by means of both ingestion and contact assays, the biological activity of three different extracts (n-hexane, methanol, and distilled water) of D. viscosa aerial part has been evaluated against Sitophilus granarius (L.) adults, an important pest of stored grains. Ingestion assays showed negligible mortality and food deterrence for all the extracts, whereas only a slight reduction of some nutritional parameters (relative growth rate, relative consumption rate, food efficiency conversion) was recorded for water extract. High contact toxicity was found only for the n-hexane extract (24 h median lethal dose LD50 = 53.20 µg/adult). This extract was further subfractioned by silica gel column chromatography and then by thin layer chromatography. Further contact toxicity bioassays highlighted two active subfractions which were analyzed by GC-MS. This revealed the occurrence, in both subfractions, of two major peaks that were identified as α- and γ- costic acid isomers. Moreover, D. viscosa active subfractions, did not cause acetylcholinesterase (AChE) inhibition; therefore, in the light of progressive limitation of compounds acting by this mechanism of action, D. viscosa represents a promising eco-sustainable source of natural products for pest control.