Phytotoxic Activity of the Natural Compound Norharmane on Crops, Weeds and Model Plants
David López-GonzálezDavid LedoLuz Cabeiras-FreijanesMercedes VerdeguerManuel J. ReigosaAdela M. Sánchez‐Moreiras
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Abstract:
Norharmane is a secondary metabolite that appears in different species of land plants. In this paper, we investigated for the first time the specificity of norharmane through germination and growth tests on some crops as Zea mays L. (maize), Triticum aestivum L. (wheat), Oryza sativa L. (rice) and Lactuca sativa L. (lettuce) and weeds as Amaranthus retroflexus L. (amaranth), Echinochloa crus-galli L. (barnyard grass), Plantago lanceolata L. (ribwort), Portulaca oleracea L. (common purslane) and Avena fatua L. (wild oat), and its phytotoxic capacity on the metabolism of adult Arabidopsis thaliana L. (thale cress) by measuring chlorophyll a fluorescence, pigment content, total proteins, osmotic potential and morphological analysis. Norharmane had an inhibitory effect on the germination of A. fatua and P. lanceolata, and the growth of P. oleracea, E. crus-galli and A. retroflexus. On adult A. thaliana plants, the compound was more effective to watering, leading to water stress that compromised the growth of the plants and ultimately affected the photosynthetic apparatus. Therefore, this research shows that norharmane not only affects seedlings’ metabolism, but also damages the metabolism of adult plants and can be a potential model for a future bioherbicide given its specificity.Keywords:
Avena fatua
Bioherbicide
Allelopathy
Avena
Phytotoxicity
Galium
Echinochloa crus-galli (E. crus-galli; barnyardgrass) is a weed widely distributed. It constitutes a serious weed problem in 42 countries and has been found in at least 27 more. It is the world's main weed of rice affecting up to 36 crops worldwide. Several biotypes of this plant, with resistance to herbicides with different modes of action have evolved. In our ongoing studies regarding the potential application of benzoxazinones and their soil degradation products for weed control, a complete structure−activity relationships (SARs) study was made by using barnyardgrass as the target plant. Compounds used in this study were previously tested on a wide variety of standard target species (STS), and they include natural allelochemicals 2-O-β-d-glucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc), 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA), and 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA), together with some degradation derivatives found in wheat crop soil and some synthetic analogues. Their phytotoxicity on E. crus-galli is discussed and compared with the results obtained from previous screening. This work constitutes the next step in the search for natural herbicide models based on benzoxazinones and their degradation products. The most active compounds were the degradation product 2-aminophenol (APH) and the synthetic analogue 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA). Their activities confirm the direction proposed in our previous SAR study, which establishes D-DIBOA to be the best lead for natural herbicide model development with benzoxazinone structure. Keywords: Rice; Echinochloa crus-galli; barnyardgrass; benzoxazinones; DIMBOA; DIBOA; 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one; bioassay; phytotoxicity
Echinochloa crus-galli
Phytotoxicity
Allelopathy
Natural product
Degradation
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In this research during 2011-12, Colletotrichum graminicola was isolated from Echinochloa spp. and studied as a biological agent for control. At first, reactions of five rice cultivars to C. graminicola were evaluated. Then, C. graminicola was inoculated on Echinochloa spp. Results indicated that the disease rating caused by this fungus in the weed was more than that in the studied rice cultivars. Also, the fungus had a significant effect on the height, fresh weight and dry weight of Echinochloa spp. and reduced them. So, C. graminicola is not recommended as a probable mycoherbicide for biological control of Echinochloa spp. in paddy fields.
Bioherbicide
Echinochloa crus-galli
Graminicola
Colletotrichum
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Studies determined the effect of sodium bisulfate (NaHSO 4 ) on the phytotoxicity, retention, uptake, and translocation of the suspension concentrate formulation of imazamethabenz in wild oats. NaHSO 4 completely solubilized this herbicide formulation when added in an equimolar concentration and did not affect herbicidal activity at NaHSO 4 concentrations below 28 mM when used in a carrier volume of 100 L ha −1 . NaHSO 4 improved phytotoxicity at a carrier volume of 33 L ha −1 . NaHSO 4 at 28 mM increased the efficacy of imazamethabenz applied as individual drops on growth chamber-grown wild oats. The herbicide retention was not changed but foliar absorption and acropetal translocation were increased, while basipetal translocation was decreased. The increase in phytotoxicity of imazamethabenz with NaHSO 4 was related to absorption of imazamethabenz by the target plants.
Avena fatua
Phytotoxicity
Avena
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Avena fatua
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Avena fatua
Galium
Avena
Winter wheat
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Ipfencarbazone exhibits excellent herbicidal activity against Echinochloa spp. and is safe for transplanted rice at a dose of 250 g a.i./ha. However, the effect of various environmental factors on its activity has not been verified. The present study evaluated the factors affecting the herbicidal activity of ipfencarbazone against Echinochloa spp. and its phytotoxicity to transplanted rice. The herbicidal activity and phytotoxicity of ipfencarbazone were barely affected by temperature, soil texture, water leakage, or flooding water depth. When an overflow was conducted artificially 6 hr after application, the herbicidal activity was stable. Furthermore, ipfencarbazone completely inhibited the emergence of Echinochloa spp. for 56 days regardless of the soil texture, water leakage and overflow conditions. When the period between application and reflooding was within 24 hr of herbicide application, the phytotoxicity of ipfencarbazone on transplanted rice was slight. These results suggest that ipfencarbazone shows stable efficacy in practical use.
Phytotoxicity
Echinochloa crus-galli
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Barnyardgrass (Echinochloa crus-galli (L.) Beauv.) is one of the most troublesome weeds in transplanted and direct-seeded rice worldwide. To develop a strategy for the biocontrol of barnyardgrass, fungal isolates were recovered from barnyardgrass plants that exhibited signs of necrosis and wilt. An isolate B-48 with a high level of pathogenicity to barnyardgrass was identified after pathogenicity tests. From cultural and DNA sequence data, this strain was identified as Colletotrichum echinochloae. The inoculation of the barnyardgrass plant with C. echinochloae caused a significant reduction in fresh weight. The isolate B-48 was highly pathogenic to barnyardgrass at the three- to four-leaf stages. When inoculated at a concentration of 1 × 107 spores/mL, barnyardgrass could achieve a reduction in fresh weight of more than 50%. This strain was safe for rice and most plant species. The results of this study indicated that this strain could be a potential mycoherbicide for barnyardgrass control in paddy fields in the future.
Echinochloa crus-galli
Bioherbicide
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Phytotoxicity
Avena fatua
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Echinochloa crus-galli is reported to be among the three most serious weeds of rice in many countries in Asia. In Malaysia, yield loss by E. crus-galli was about 41%. Selective chemical herbicides are primary means to control the grass. However, the extended use of the herbicides may develop negative implication to the environment and public health. Several fungal pathogens have been reported to attack barnyard grass (E. crus-galli complex) in various parts of the world. This study was to isolate, identify and evaluate the native fungi from diseased barnyard grass in paddy field, for potential as bioherbicide. From surveys carried out in 2003 to 2004 throughout the Peninsular Malaysia, several fungi species were identified to be associated with the diseases. A total of 82 isolates from 12 fungus genera have been isolated. Among the fungi were E. monoceras, E. longirostratum and Curvularia lunata. The fungus, E. monoceras, was consistently found associated with the disease, virulent, stable and has the ability to produce spores profusely in culture. These characteristics suggest that it can be used as biological control agent for the grass.
Echinochloa crus-galli
Bioherbicide
Paddy field
Curvularia
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Fifteen novel derivatives of D-DIBOA, including aromatic ring modifications and the addition of side chains in positions C-2 and N-4, had previously been synthesised and their phytotoxicity on standard target species (STS) evaluated. This strategy combined steric, electronic, solubility and lipophilicity requirements to achieve the maximum phytotoxic activity. An evaluation of the bioactivity of these compounds on the systems Oryza sativa-Echinochloa crus-galli and Triticum aestivum-Avena fatua is reported here.All compounds showed inhibition profiles on the two species Echinochloa crus-galli (L.) Beauv. and Avena fatua L. The most marked effects were caused by 6F-4Pr-D-DIBOA, 6F-4Val-D-DIBOA, 6Cl-4Pr-D-DIBOA and 6Cl-4Val-D-DIBOA. The IC(50) values for the systems Echinochloa crus-galli-Oryza sativa and Avena fatua-Triticum aestivum for all compounds were compared. The compound that showed the greatest selectivity for the system Echinochloa crus-galli-Oryza sativa was 8Cl-4Pr-D-DIBOA, which was 15 times more selective than the commercial herbicide propanil (Cotanil-35). With regard to the system Avena fatua-Triticum aestivum, the compounds that showed the highest selectivities were 8Cl-4Val-D-DIBOA and 6F-4Pr-D-DIBOA. The results obtained for 6F-4Pr-D-DIBOA are of great interest because of the high phytotoxicity to Avena fatua (IC(50) = 6 µM, r(2) = 0.9616).The in vitro phytotoxicity profiles and selectivities shown by the compounds described here make them candidates for higher-level studies. 8Cl-4Pr-D-DIBOA for the system Echinochloa crus-galli-Oryza sativa and 6F-4Pr-D-DIBOA for Avena fatua-Triticum aestivum were the most interesting compounds.
Echinochloa crus-galli
Avena fatua
Phytotoxicity
Avena
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