Lavender as a source of novel plant compounds for the development of a natural herbicide.

In a previous study, lavender (Lavandula spp.) was found to be highly phytotoxic towards annual ryegrass (Lolium rigidum, ARG), a major weed of winter wheat crops in Australia. This research aimed to further explore this relationship and determine the chemical(s) responsible for the observed effect. In bioassay, it was determined that the stem and leaf extract of L. x intermedia cv. Grosso ranked highest and had the potential to reduce significantly the root growth of several plant species. An extract concentration of 10% almost completely inhibited ARG root growth. When the extract was tested for stability, there was no loss in phytotoxicity after the 256 day trial. Via bioassay-guided fractionation and chromatographic techniques, it was determined that the sub-fraction consisting of coumarin and 7-methoxycoumarin was most phytotoxic towards ARG. Chemoassays of 18 structural analogues of coumarin showed that coumarin itself was the most phytotoxic and largely responsible for the observed phytotoxicity of the extract. Soil trials were conducted using pure coumarin and the lavender extract, and in both instances, shoot length and weight were significantly reduced by post-emergence application at all concentrations evaluated.

Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates.

An investigation of the chemical basis for rice allelopathy to the rice weed arrowhead (Sagittaria montevidensis) was undertaken using GC/MS and GC/MS/MS techniques. Twenty-five compounds were isolated and identified from the root exudates of both allelopathic and non-allelopathic rice varieties. Phenolics, phenylalkanoic acids, and indoles were among the chemical classes identified. Two indoles previously unreported in rice were detected in the exudates, 5-hydroxy-2-indolecarboxylic acid and 5-hydroxyindole-3-acetic acid. Several other compounds identified in this study have not previously been reported in rice root exudates, namely mercaptoacetic acid, 4-hydroxyphenylacetic acid, and 4-vinylphenol. The levels of 15 compounds present in the exudates were quantified using GC/MS/MS. Six of the seven most abundant compounds were phenolic acids. Significant differences exist between the allelopathic and non-allelopathic cultivars in their production of three of these six compounds. Greater amounts of trans-ferulic acid, p-hydroxybenzoic acid, and caffeic acid were detected in the exudates of allelopathic cultivars. The seventh compound, abietic acid, was significantly higher in the non-allelopathic cultivars.

Evaluation of putative allelochemicals in rice root exudates for their role in the suppression of arrowhead root growth.

In previous studies, 15 putative allelopathic compounds detected in rice root exudates were quantified by GC/MS/MS. In this study, multiple regression analysis on these compounds determined that five selected phenolics, namely caffeic, p-hydroxybenzoic, vanillic, syringic, and p-coumaric acids, from rice exudates were best correlated with the observed allelopathic effect on arrowhead (Sagittaria montevidensis) root growth. Despite this positive association, determination of the phenolic acid dose-response curve established that the amount quantified in the exudates was much lower than the required threshold concentration for arrowhead inhibition. A similar dose-response curve resulted from a combination of all 15 quantified compounds. Significant differences between the amounts of trans-ferulic acid, abietic acid, and an indole also existed between allelopathic and non-allelopathic rice cultivars. The potential roles of these three compounds in rice allelopathy were examined by chemoassay. Overall, neither the addition of trans-ferulic acid nor 5-hydroxyindole-3-acetic acid to the phenolic mix significantly contributed to phytotoxicity, although at higher concentrations, trans-ferulic acid appeared to act antagonistically to the phytotoxic effects of the phenolic mix. The addition of abietic acid also decreased the inhibitory effect of the phenolic mix. These studies indicate that the compounds quantified are not directly responsible for the observed allelopathic response. It is possible that the amount of phenolic acids may be indirectly related to the chemicals finally responsible for the observed allelopathic effect.

Correlation between phytotoxicity on annual ryegirass (Lolium rigidum) and production dynamics of allelochemicals within root exudates of an allelopathic wheat.

An improved allelopathic correlation between phytotoxicity measured in root growth bioassay upon annual ryegrass (Lolium rigidum Gaud.) and the concentrations of a selection of dynamically produced allelochemicals quantified in the root exudates of cv. Khapli wheat (Triticum turgidum ssp. durum (Desf.) Husn.) monitored during the first 15 days of wheat seedling growth in a sterile, agar-water medium, has been established. Changes over the 15-day growth period in the quantities of five exuded benzoxazinones and seven phenolic acids were measured simultaneously using GC/MS/MS. Substantiating pure compound dose-response measurements were conducted over a range of concentrations for the putative allelochemicals within the wheat exudates. One synergism-based proposal using the monitored compounds to explain the observed low-exudate-concentration phytotoxicity was explored, but was found to be experimentally inadequate.

Phytotoxic effects of wheat extracts on a herbicide-resistant biotype of annual ryegrass (Lolium rigidum).

Thirty-nine wheat accessions were used to evaluate their extract phytotoxicity against annual ryegrass (Lolium rigidum Gaud.). Aqueous extracts of wheat shoot residues significantly inhibited the germination and root growth of a biotype of annual ryegrass resistant to herbicides of acetyl CoA carboxylase inhibitors (group A), acetolactate synthase inhibitors (B), photosystem II inhibitors (C), and tubulin formation inhibitors (D). The germination of the herbicide resistant (HR) biotype was inhibited by 3-100%, depending upon the wheat accession. The phytotoxic effects on ryegrass root growth ranged from 12% stimulation to 100% inhibition, compared to a control. The germination and root growth of a herbicide-susceptible (HS) biotype of annual ryegrass were also inhibited by the wheat extracts, with germination inhibited by 4-100%, and root growth by 19-100%. Bioassays with two known wheat allelochemicals showed that p-coumaric acid and propionic acid significantly inhibited the growth of both HR and HS biotypes of annual ryegrass. The two compounds completely inhibited the root growth of HR ryegrass at concentrations greater than 5.0 mM. In comparison with p-coumaric acid, propionic acid was more inhibitory to seed germination, shoot, and root growth of both ryegrass biotypes. The root growth of the HR biotype was more sensitive when exposed to wheat extracts, to p-coumaric acid, and to propionic acid. The results suggest that residues of certain wheat cultivars with strong allelopathic potential could provide a nonherbicidal alternative for the management of herbicide-resistant weed species.

Biochemical basis for wheat seedling allelopathy on the suppression of annual ryegrass (Lolium rigidum).

The chemical basis for wheat seedling allelopathy on the growth of annual ryegrass was investigated by the identification and quantification of multiple allelochemicals from wheat seedlings. Results indicated that 58 wheat accessions differed significantly in seedling allelopathy and inhibited the root growth of ryegrass from 10 to 91%, depending on accession. Analysis of allelochemicals by GC/MS/MS indicated that allelopathy was significantly correlated with the levels of measured allelochemicals in the shoots and roots of young wheat seedlings. Ryegrass root growth was also negatively correlated with the levels of p-hydroxybenzoic, vanillic, and trans-ferulic acids in root exudates. Wheat allelopathic potential was negatively correlated with the levels of the eight known allelochemicals quantified in the shoots, roots, and water-agar medium, with multiple regression coefficients (r) of -0.61, -0.71, and -0.71, respectively. In comparison with weakly allelopathic accessions, strongly allelopathic accessions produced significantly higher amounts of allelochemicals in the shoots and roots of the wheat seedlings and also exuded larger quantities of allelochemicals into the growth medium. Wheat accessions with strong seedling allelopathy might be useful for management of weeds during the establishment stage, thereby reducing the need for commercial herbicides in early-season application.