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Xanthoxyline (

In this laboratory bioassay, crude aqueous extract of Spirulina platensis (Nordst) Geitl. was extracted with 90% aqueous ethanol and 80% aqueous ethanol to achieve three subfractions, green powder (F1), pale-green powder (F2) and deep-blue powder (F3). Each of these subfractions was evaluated for allelopathic activity on Chinese amaranth (Amaranthus tricolor L.) and barnyardgrass (Echinochloa crus-galli (L.) Beauv.). The plant seeds were germinated in vials with three subfractions (250-2000 mg/l concentrations) and distilled water was used as a negative control. The results indicated that subfraction F3 had the highest inhibitory effect on both of the tested plants. All subfractions had an absorbance ratio (A620/A280) lower than the original aqueous extract, suggesting that a denaturation event of the C-phycocyanin (C-PC) component had occurred during the extraction process. After heating a commercial C-PC solution at 90oC for 3 h, the absorbance ratio changed to 0.46, and likewise allelopathic assay revealed that the decolorized C-PC solution retained its allelopathic potential on the tested plants. To confirm these findings, S. platensis powder was extracted with distilled water at 90oC for 3 h and tested for its allelopathic potential using standard Petri dish assay at concentrations of 0.625-5%. The results showed that the hot aqueous extract had an absorbance ratio of 0.38, and its allelopathic activities were similar to those of the aqueous extract. Furthermore, it was found that although C-PC in aqueous extractions denatured, it still retained its allelopathic potential on the tested plants.

Amino acids have a wide range of biological activities, which usually rely on the stereoisomer presented. In this study, glycine and 21 common α-amino acids were investigated for their herbicidal property against Chinese amaranth (Amaranthus tricolor L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv.). Both d- and l-isomers, as well as a racemic mixture, were tested and found that most compounds barely inhibited germination but moderately suppressed seedling growth. Various ratios of d:l-mixture were studied and synergy between enantiomers was found. For Chinese amaranth, the most toxic d:l-mixtures were at 3:7 (for glutamine), 8:2 (for methionine), and 5:5 (for tryptophan). For barnyard grass, rac-glutamine was more toxic than the pure forms, however, d-tryptophan exhibited greater activity than racemate and l-isomer, indicating the sign of enantioselective toxicity. The mode of action was unclear, but d-tryptophan caused bleaching of leaves, indicating pigment synthesis of the grass was inhibited. The results highlighted the enantioselective and synergistic toxicity of some amino acids, which relied upon plant species, chemical structures, and concentrations. Overall, our finding clarifies the effect of stereoisomers, and provides a chemical clue of amino acid herbicides, which may be useful in the development of herbicides from natural substances.

Thirty-seven commercial aldehydes containing aliphatic chains and aromatic rings as well as heteroaromatic rings were evaluated for their inhibitory activities against Chinese amaranth (Amaranthus tricolor L.) and barnyardgrass (Echinochloa crus-galli (L.) Beauv). Polysorbate 80 (Tween® 80) was used as a surfactant and the research was preliminarily conducted at 400 μM of all aldehydes. Among these aldehydes, (E)-cinnamaldehyde (7) showed the greatest inhibitory effect on seed germination, shoot and root growth of Chinese amaranth by 54.55%, 75.53%, and 85.13% respectively. Similarly, (E)-crotonaldehyde (5), a related α,β-unsaturated aldehyde, inhibited the germination and seedling growth of the tested species at a high percentage. Apart from these two unsaturated aldehydes, no other aliphatic aldehydes had a harmful effect on Chinese amaranth. In terms of benzaldehyde (6), it had no effect on the tested plant; however, many of its derivatives displayed some inhibitory activity. Furthermore, for the ten common heteroaromatic aldehydes, picolinaldehyde (32) had a high inhibitory effect on Chinese amaranth which closely related to the effect of (E)-crotonaldehyde (5) and (E)-cinnamaldehyde (7), whereas, other heteroaromatic aldehydes showed lower effects. In the case of a monocot plant, barnyardgrass, no tested aldehydes reduced seed germination, however, (E)-cinnamaldehyde (7), 2,4,6-trimethoxybenzaldehyde (16) and 4-(dimethylamino)benzaldehyde (24) could inhibit the seedling growth of the plant with low to moderate levels. The herbicidal effects of the most active aldehydes were then further investigated in order to find the minimum concentration of these aldehydes suppressing the germination and growth of the tested plants. At concentrations as low as 50-100 μM some aldehydes could inhibit the seedling growth of the tested species. The structure-activity relationship (SAR) study reported here demonstrates the chemical clues governing the inhibitory activity of aldehydes which could be utilized in the development of highly effective herbicides in the near future.

Lemongrass ( Cymbopogon citratus ) essential oil was identified by GC–MS for their major compound constituents; six compounds representing 92.59% of the total essential oil were identified. The main constituent was citral (76.00%). In a laboratory bioassay, high concentration of essential oil significantly inhibited germination and seedling growth of Echinochloa crus-galli and affecting α-amylase activity of seeds. In a glass house bioassay, essential oil at concentrations of 1.25, 2.5, 5 and 10% (v/v) was foliar-applied on E. crus-galli at 28 days after sowing at spray volume of 1000 L ha −1 . Observation of leaf wilt symptoms was noted at 6 h after treatment. Chlorophyll a, b and carotenoid content was decreased with concentrations of essential oil, indicating that essential oil interferes with photosynthetic metabolism. C. citratus essential oil caused an electrolyte leakage indicating membrane disruption and loss of integrity. Treated leaves exhibited an increase in thiobarbituric acid reactive substances (TBARS), suggesting lipid peroxidation. It is to conclude that essential oil is phytotoxic and could be utilized as a natural herbicide for future weed control.

A bioassay-guided fractionation of the allelochemicals of the ethyl acetate fraction extracted from Aglaia odorata led to isolation of a bisamide, odorine. The growth inhibitory effects of odorine and ethyl acetate fraction were studied for comparison on Echinochloa crus-galli. Odorine and ethyl acetate fraction of A. odorata could inhibit the germination and seedling growth of E. crus-galli, with ethyl acetate fraction being more potent. Thus, ethyl acetate fraction was selected for further experiment, E. crus-galli seeds were studied the effects of the ethyl acetate fraction from A. odorata leaves in wettable powder formulation on imbibition and α-amylase activity. It was found that treated seeds showed lower imbibition and α-amylase activity. The results of cytogenetic bioassay in Allium cepa roots showed that ethyl acetate fraction inhibited cell mitosis and induced mitotic abnormalities resulting from its action on chromatin organization and mitotic spindle in the exposed roots.

This experiment was conducted to determine the potential allelopathic effects of the aqueous extracts and dried leaf powder of Suregada multiflorum and to find the herbicidal effects of its granule on the weed species, barnyardgrass (Echinochloa crus-galli) and slender amaranth (Amaranthus viridis), in various growth media (germination paper, sand, and soil). Observations in this study demonstrated that the potential and magnitude of their inhibitory effects varied among the plant parts. The leaves and branches possessed the strongest inhibition levels, followed by the bark. The aqueous extract from the leaves of S. multiflorum had a remarkably stronger inhibitory effect on the germination and growth of slender amaranth, compared with barnyardgrass; when applied at the concentration of 100 g L–1, it completely inhibited the germination and initial seedling growth of slender amaranth. In addition, all the treatments of the dried leaf powder had stronger inhibition effects than the aqueous extract. Interestingly, the inhibitory effects of the dried leaf granule of S. multiflorum were stronger than the effects of the dried leaf powder at equal rates. The degree of inhibitory effect of the S. multiflorum granule, applied in various growing media, can be classified in order of decreasing inhibition as germination paper = sand > clay soil. The present study indicates that the S. multiflorum granule product that was developed in this research has the potential to provide a powerful organic herbicide for controlling slender amaranth.

Bioassay-guided fractionation of the ethyl acetate extract of the Zanthoxylum limonella Alston fruits led to the isolation of a phenolic compound named xanthoxyline. The allelopathic effects of xanthoxyline were evaluated on Chinese amaranth (Amaranthus tricolor L.) and Barnyardgrass (Echinochloa crus-galli (L.) Beauv.) under laboratory conditions. At a concentration of 2500 μM, xanthoxyline completely inhibited seed germination and growth of Chinese amaranth, while this compound showed a significantly inhibitory effect on seed germination of Barnyardgrass by 43.59% and inhibited shoot and root length by 71.56% and 87.48%, respectively. To determine the mechanism through which xanthoxyline exerts its toxicity, the cytogenetic bioassay was conducted. Roots of Allium cepa L. (onion) were treated with a series of concentrations, ranging from 15.625 to 125 μM for 18 h. Cytogenetic studies of onion roots showed a decrease of the mitotic index in the exposed roots dependent on the concentration of xanthoxyline. Likewise, the mitotic phase index was altered in onion incubated with xanthoxyline. Analyses of the abbreviation types showed spindle disturbances at late prophase, sticky metaphase, c-mitosis, non-oriented chromosome at metaphase, sticky anaphase, delayed anaphase and diagonal at telophase for the onion roots exposed to xanthoxyline.

An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

The unsubstituted pyrylium nucleus is shown to undergo reaction with cuprate or secondary Grignard organometallic reagents to give intermediate 4-substituted pyrans which are converted into the corresponding 4-substituted pyrylium salts (7 examples) in fair to good overall yield. The synthetic utility of the 4-substituted pyrylium heterocycles is demonstrated by their reaction with organolithium reagents to give 3,5-disubstituted dienals in a highly stereospecific manner (7 examples) via electrocyclic ring opening of the intermediate 2-substituted pyrans.

A new stereocontrolled route to conjugated dienynes is described, utilising organometallic addition to pyrylium salts followed by Wittig homologation and dehydrohalogenation. The utility of this methodology is illustrated in the first total synthesis of the marine metabolite Carduusyne A.

A methanolic extract in wettable powder from the leaves of Jasminum officinale f. var. grandiflorum (Linn.) Kob. (JWP) was inhibitory to germination and seedling growth of Echinochloa crus-galli (L.) Beauv. weeds. The inhibition percentages on E. crus-galli seed germination treated with 500 to 8,000 ppm for 7 days was about 0 to 70%, respectively, whereas shoot length was inhibited from 19.04 to 71.82% and root length was 76.31 to 100% inhibition, respectively. The imbibition and α-amylase activities in the treated E. crus-galli seeds were progressively depressed with increasing JWP concentrations. The obtained results suggest that JWP inhibited imbibition and α-amylase activity in E. crus-galli seeds during germination. Keywords: Allelopathy, α-amylase, Echinochloa crus-galli, Jasminum officinale, seed imbibition

The unsubstituted pyrylium nucleus is shown to undergo reaction with cuprate or secondary Grignard organometallic reagents to give intermediate 4-substituted pyrans which are converted into the corresponding 4-substituted pyrylium salts (7 examples) in fair to good overall yield. The synthetic utility of the 4-substituted pyrylium heterocycles is demonstrated by their reaction with organolithium reagents to give 3,5-disubstituted dienals in a highly stereospecific manner (7 examples) via electrocyclic ring opening of the intermediate 2-substituted pyrans.

Methanolic extracts prepared from dried leaves of Jasminum officinale f. var. grandiflorum (L.) Kob. (Spanish jasmine) inhibited seed germination and stunted both root and shoot length of the weeds Echinochloa crus-galli (L.) Beauv. and Phaseolus lathyroides L. The main active compound was isolated and determined by spectral data as a secoiridoid glucoside named oleuropein. In addition, a decrease in allelopathic efficacy appeared as the decomposition periods increased. The mitotic index in treated onion root tips decreased with increasing concentrations of the extracts and longer periods of treatment. Likewise, the mitotic phase index was altered in onion incubated with crude extract. Furthermore, crude extract produced mitotic abnormalities resulting from its action on chromatin organization and mitotic spindle.

An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

Flash vacuum pyrolysis of cyclopropene–anthracene adducts 4, 6 and 8 results in ring opening of the cyclopropane moiety to yield 5, 7 and 5e, respectively.