Dynamic root exudation of phenolic allelochemicals from Johnson grass (Sorghum halepense)

The phenolic allelochemicals from the root exudates of Johnson grass (Sorghum halepense) were collected at different developmental stages and analyzed using high performance liquid chromatography‐ultraviolet/photo‐diode array. The results revealed that three simple phenolic components, p‐hydroxybenzoic acid, p‐hydroxybenzaldehyde and ethyl p‐hydroxybenzoate, along with two flavonoids, diosmetin (3′,5,7‐trihydroxy‐4′‐methoxyflavone) and tricin (5,7,4′‐trihydroxy‐3′,5′‐dimethoxyflavone), were found in the root exudates of Johnson grass. However, the major phenolic compounds varied and the quality of each compound was dynamic at different developmental stages: the only phenolic compound that was detected in the seedling stage was p‐hydroxybenzoic acid; three simple phenolic allelochemicals, p‐hydroxybenzoic acid, p‐hydroxybenzaldehyde and ethyl p‐hydroxybenzoate, were found in the jointing stage; and five compounds, including the two flavonoids, tricin and diosmetin, appeared in the reproductive stage along with the other three simple phenolic allelochemicals. The highest diversity in phenolic constituents was in the reproductive stage, with five allelochemicals. Only p‐hydroxybenzoic acid was found in the whole life cycle of Johnson grass, with a range of 2.9 nmol to 6.8 nmol per plant per day. p‐Hydroxybenzaldehyde had the highest quality among all the compounds, with the highest releasing rate of 26.8 nmol per plant per day. The lowest‐content compounds were the two flavonoids, with the highest quality of 1.8 nmol per plant per day. The results suggest that the temporal dynamic of phenolic allelochemicals in the root exudates of Johnson grass corresponds with the dynamic of development.     

Shift of allelochemicals from Sorghum halepense in the soil and their effects on the soil's bacterial community

Johnsongrass (Sorghum halepense [L.]Pers.), an exotic invasive weed in China, secretes the phenolic compounds, p‐hydroxybenzoic acid (p‐HBA) and p‐hydroxybenzaldehyde (p‐HBAL), as the dominant allelochemicals in the root exudates. To better understand how these two allelochemicals affect the soil microbial community in the rhizosphere of S. halepense, the fate of these compounds in the invaded soil and the effect of these phytotoxins on the soil bacterial community were evaluated. The concentrations of the allelochemicals in the soil were determined by a high‐performance liquid chromatography‐ultraviolet/photodiode array after 1, 2, 4, 6, 12 and 24 h of treatment. MiSeq sequencing was undertaken to understand how the bacterial populations in the soil were affected by the allelochemicals. The HPLC results indicated that p‐HBA was degraded by the microorganisms that were present in the soil after 1 h and disappeared after 6 h of incubation. The compound, p‐HBAL, initially was converted to p‐HBA and then the p‐HBA broke down, disappearing after 12 h of incubation in non‐sterile soil. Both p‐HBA and p‐HBAL were stable under sterile soil conditions for up to 24 h. The relative abundance of Proteobacteria was significantly inhibited. However, those of Acidobacteria, Chloroflexi, Verrucomicrobia and Cyanobacteria were increased by the p‐HBAL treatment. These findings suggest that allelochemicals from S. halepense might affect the bacterial community composition in the soil.     

Synthesis and Evaluation of New Ethyl 2,3- Dihydro-3-oxoisothiazolo[5,4-b]pyridine- 2-alkanoate Derivatives as Potential Herbicides

Several ethyl 2,3-dihydro-3-oxoisothiazolo[5,4-b]pyridine-2-alkanoate derivatives were synthesized as herbicides. Only 5-methyl derivatives inhibited both hypocotyl and root growth in the lettuce (Lactuca sativa L.) seedling test at 100 mg litre^-1. Only ethyl propionate and valerate derivatives showed significant inhibition at 0·1 mg litre^-1, whereas ethyl acetate or butyrate derivatives were inactive. Contrary to unoxidized derivatives, the inhibitory effect of 1-oxide and 1,1-dioxide derivatives was strongly dependent on concentration; ethyl 2,3-dihydro-5-methyl-3-oxoisothiazolo[5,4-b]pyridine-2-propionate 1,1-dioxide inhibited 100% of germination at 100 mg litre^-1 and 45% of lettuce seedling growth at 0·1 mg litre^-1. Quantitative structure–inhibition of growth relationship analysis carried out by adaptive least-squares (ALS) method gave a good correlation with small and hydrophobic 5-substituents as well as with odd carbon-chain ethyl alkanoates in position 2. Active compounds did not show auxin-like activity from 0·1 to 100 mg litre^-1. © 1997 SCI.     

Herbicidal potential and quantification of causative allelochemicals from several Compositae weeds

Compositae plants contain biologically active substances that are allelopathic to weed species. Aqueous extracts from leaves of 16 plants were bioassayed against lucerne (Medicago sativa) to determine their allelopathic effects, and the results showed the highest inhibition for the extracts from Lactuca sativa, Xanthium occidentale and Cirsium japonicum. The extracts applied to filter paper in Petri‐dish bioassay tests significantly inhibited root growth of lucerne. Extracts of 40 g dry tissue L^?1 from L. sativa, X. occidentale and C. japonicum were completely inhibitory to lucerne root growth, but hypocotyl growth of lucerne was less sensitive. Although allelopathic effects of methanol extracts were much less than those of coumarin or alachlor, early seedling growth of both lucerne and Echinochloa crus‐galli was significantly reduced by methanol extracts. Mixture of L. sativa, X. occidentale and C. japonicum extracts had more inhibitory effects on test plants than each single extract treatment. By means of high‐performance liquid chromatography, responsible causative allelopathic substances present in L. sativa, X. occidentale and C. japonicum were isolated from various fractions and identified as coumarin, trans‐cinnamic acid, o‐coumaric acid and p‐coumaric acid. These results suggest that some Compositae have various herbicidal potentials, and that their activities, types and amount of causative compounds differ, depending on the plant species.     

Effects of ferrous iron (Fe) on the germination and root elongation of paddy rice and weeds

Laboratory experiments were conducted to analyze the iron (Fe) tolerance of paddy weeds and rice varieties (Oryza sativa) for germination and root elongation. Under a waterlogged soil condition, the Fe(II) content in a soil solution increased with an increase in the ratio of rice straw to the soil. In the presence of 0.9% (w/w) straw to soil, which corresponds approximately to 8 t of straw applied to an area of 1 ha × 10 cm depth in the field, ～80 mg L^?1 of Fe(II) was produced in the soil solution. Based on this result, the seeds of rice and the weeds were incubated in a solution with <100 mg L^?1 of Fe(II). The presence of 100 mg L^?1 of Fe(II) suppressed the germination of Echinochloa crus‐galli var. crus‐galli, Cyperus serotinus, Cyperus difformis, and Monochoria korsakowii. However, it had no effect on the germination of Echinochloa oryzicola, Schoenoplectus juncoides (= Scirpus juncoides var. ohwianus), and Monochoria vaginalis. This level of Fe tolerance was the same as that of rice. These findings suggest that E. oryzicola, S. juncoides, and M. vaginalis can grow under more severe conditions than E. crus‐galli, C. serotinus, C. difformis, and M. korsakowii. In relation to seminal root elongation, the order of tolerance of Fe toxicity was O. sativa cv. Dunghan Shali > O. sativa cv. Hoshinoyume > E. oryzicola > M. vaginalis > S. juncoides. Thus, the results show that the tolerance of rice is greater than that of E. oryzicola, which had a comparatively strong tolerance among the weeds examined, and also that there are differences in tolerance among the rice varieties. These findings suggest that the difference in Fe tolerance is involved in weed control systems when organic materials are applied. If this difference is an important factor in the weed control system, Fe‐tolerant rice varieties, like cv. D. Shali, could facilitate weed control systems due to their higher Fe tolerance ability.     

Effects of momilactone on the protein expression in Arabidopsis germination

Although momilactone is known to play an important role in the allelopathy of rice (Oryza sativa L.), there is no information available about the mode of action of momilactone on the allelopathy of Arabidopsis. The present research describes the allelopathic activity of momilactone A and B on the germination of Arabidopsis thaliana and the effects of momilactone A and B on protein expression during germination. Momilactone A and B inhibited the germination of Arabidopsis at concentrations >30 and 10 μmol L^?1, respectively. The protein bands of 18, 19 and 21 kDa on sodium dodecyl sulphate‐polyacrylamide gel electrophoresis (SDS‐PAGE) were abundant in the momilactone A‐ and B‐treated Arabidopsis compared with the control. The protein bands of 18, 19 and 21 kDa were identified by the N‐terminal amino acid sequencing as cruciferin 2, cruciferina and cruciferin 3, respectively. Cruciferins and cruciferina are important storage proteins and play an important role as the initial source of nitrogen for seed germination. These results suggest that momilactone A and B may inhibit the germination of Arabidopsis seeds by inhibiting the degradation process of cruciferin and cruciferina.     

Phytotoxic and antiphytopathogenic compounds from Thai Alpinia galanga (L.) Willd. rhizomes

The management of weeds and diseases that are caused by phytopathogenic fungi is important for preventing the loss of agricultural products. The aim of the present study was to identify phytotoxic and antiphytopathogenic agents from the Thai Alpinia galanga rhizome. Extracts of the dried rhizomes of A. galanga (Zingiberaceae) were separated and tested for phytotoxic activity against lettuce (Lactuca sativa L. cv. Great Lakes) and Italian ryegrass (Lolium multiflorum Lam. cv. Wasefudou) and for antiphytopathogenic activity against Alternaria porri, Colletotrichum gloeosporioides, Fusarium oxysporum and Phytophthora nicotianae. 1′‐Acetoxychavicol acetate ( 1 ) was identified as one of the main components, together with trans‐p‐coumaryl acetate ( 3 ) and trans‐p‐acetoxycinnamyl acetate ( 2 ). 1′‐Acetoxychavicol acetate ( 1 ) was solvolyzed with 2% EtOH to yield trans‐p‐coumaryl ethyl ether ( 6 ), trans‐p‐coumaryl acetate ( 3 ) and trans‐p‐coumaryl alcohol ( 5 ). 1′‐Acetoxychavicol acetate ( 1 ) completely inhibited the root growth of the lettuce seedlings at 50 μg mL^–1, but had a weaker inhibitory effect on the growth of Italian ryegrass. 1′‐Acetoxychavicol acetate also inhibited the growth of P. nicotianae and A. porri, with minimum inhibition concentration values of 15.6 and 31.5 μg mL^–1, respectively. The plant growth‐inhibitory activity and fungal growth‐inhibitory activity of trans‐p‐coumaryl acetate ( 3 ), trans‐p‐coumaryl ethyl ether, trans‐p‐coumaryl alcohol ( 5 ) and trans‐p‐acetoxycinnamyl acetate ( 2 ) were lower than those of 1′‐acetoxychavicol acetate. A structure–activity relationship suggested that the strong phytotoxic and antiphytopathogenic activity of 1′‐acetoxychavicol acetate relied on the 1′‐acetoxyl group.     

Allelopathy and the active metabolites of the endophytic fungus,Alternaria J46, from Platycladus orientalis

The endophytic fungus, Alternaria J46, was isolated from the stem of the medicinal plant, Platycladus orientalis. A suspension of Alternaria J46 mycelial segments and the culture filtrates of the fungi exhibited marked seed germination inhibition against the monocot wheat, large crabgrass, bromegrass, rice and barnyardgrass and weak inhibition against the dicot redroot pigweed and morning glory, but it was safe for use on soybean, rape, cucumber, tomato, lettuce and radish crops. It is possible to use J46 culture filtrates in order to prevent monocot weeds in dicot cropland. Three active metabolites were isolated from an extract of the fungus cultures and elucidated as 3‐acetyl‐5‐sec‐butyltetramic acid (1, tenuazonic acid), 3‐acetyl‐5‐iso‐butyltetramic acid (2, vivotoxin II) and cyclo‐(L‐leucyl‐L‐proline) (3). Among these three compounds, compounds 1 and 2 showed significant phytotoxic effects on the seed germination of large crabgrass, while compound 3 exhibited weak activity, and all were safe for lettuce at 100 μg mL^?1. Accordingly, compounds 1 and 2 were the main active metabolites that were responsible for endophytic fungus Alternaria J46's strong seed germination inhibition against monocotyledons.     

Allelopathic potential of Acacia melanoxylon on the germination and root growth of native species

Water extracts that were obtained from the flowers and phyllodes of Acacia melanoxylon were used to determine their allelopathic potential in relation to the germination and seedling growth of the native species, cocksfoot (Dactylis glomerata), perennial ryegrass (Lolium perenne), and common sorrel (Rumex acetosa), as well as a general biotest specie, lettuce (Lactuca sativa), in laboratory bioassays. The flowers and phyllodes of A. melanoxylon were soaked separately in distilled water in a ratio of 1:1 (w/v) for 24 h in order to prepare the aqueous extracts. Distilled water was used as the control. The seeds of the target species were germinated in Petri dishes and counted daily for up to 7 days. The A. melanoxylon flower extract (100%, 75%, and 50%) decreased the seed germination of D. glomerata, R. acetosa, L. perenne, and L. sativa. The flower extract caused the most reduction in the germination index and germination speed in D. glomerata, L. perenne, and L. sativa. The mean LC₅₀ value of the A. melanoxylon flower and phyllode extracts in relation to the germination inhibition of L. perenne was 43% and 41%, respectively, 40% and 38%, respectively, in R. acetosa, and 53% and 41%, respectively, in L. sativa. All four concentrations of the flower extract proved to be more phytotoxic than the phyllode extract, reducing the root length of all four species, while the phyllode extract decreased the root length of L. perenne and R. acetosa at the 100% concentration. The L. perenne and D. glomerata grass seeds were more sensitive regarding germination, as compared to L. sativa and R. acetosa. The flower aqueous extract of A. melanoxylon was more phytotoxic, as compared to the phyllode aqueous extract, even at the lowest concentration (25%).     

Potential allelopathic effects of Mikania micrantha on the seed germination and seedling growth of Coix lacryma‐jobi

The allelopathic potential of Mikania micrantha H.B.K. to affect the seed germination and seedling growth of Coix lacryma‐jobi L. was investigated. Water‐soluble allelopathic substances were found in the water extracts of M. micrantha. The effect of the water extracts on the seed germination and seedling growth of C. lacryma‐jobi was concentration‐dependent. The water extracts from the different plant parts (leaf, stem, and root) of M. micrantha differed in their effect on the germination and seedling growth of C. lacryma‐jobi, with the effect of the leaf extract being the least inhibitory. The malondialdehyde (MDA) content in the C. lacryma‐jobi seedlings increased by 64%, 45%, and 52% of the control with increasing concentrations of the extracts of the root, stem, and leaf (80, 400, and 400 g L^?1, respectively). The extract from the M. micrantha roots significantly increased the catalase (CAT) activity of the C. lacryma‐jobi seedlings (48% and 54% of the control at the concentrations of 20 g L^?1 and 80 g L^?1, respectively). The extracts from the leaves and stems at low concentrations increased the CAT activity, but at high concentrations, the extracts decreased the CAT activity. The extracts from the roots, stems, and leaves at concentrations of 80, 400, and 400 g L^?1 also significantly decreased the peroxidase (POD) activity of the C. lacryma‐jobi seedlings to 27%, 52%, and 34% of the control, respectively. These results indicate that the water extracts of M. micrantha could inhibit the seed germination and seedling growth of C. lacryma‐jobi through the regulation of anti‐oxidase activity, such as POD and CAT in the cells. The growth inhibition of the C. lacryma‐jobi seedlings is probably related to injury after oxidization of the cell membranes with the increase of MDA content.     

Synthesis and herbicidal potential of substituted aurones

BACKGROUND: With the objective of exploring the herbicidal activity of substituted aurones, a series of 4,6‐disubstituted and 4,5,6‐trisubstituted aurones were synthesised, and their herbicidal activities against Brassica campestris L. and Echinochloa crusgalli (L.) Beauv. were evaluated in laboratory bioassays. Effects of some of the compounds were evaluated on seed germination. The most active compounds in the laboratory were evaluated in the greenhouse. RESULTS: The compounds were characterised by ¹H NMR, ¹³C NMR and HRMS; some of them were further identified by IR. A (Z)‐configuration was assigned to the aurones, based on spectroscopic and crystallographic data. Bioassay results of root growth showed that the aurones had a moderate herbicidal activity against the dicotyledonous plant Brassica campestris. (Z)‐2‐Phenylmethylene‐4,6‐dimethoxy‐3(2H)‐benzofuranone(6o) was the most active compound, with 81.3 and 88.5% inhibition at 10 and 100 µg ml^?1 respectively, equal to the activity of mesotrione. Some of the aurones possessed some inhibition of germination on several plant species. For glasshouse tests, the substituted aurones had lower herbicidal activity than metolachlor and mesotrione. CONCLUSION: It is possible that aurone derivatives, which possess structures different from those of the commercial herbicides, may become novel lead compounds for the development of herbicides against dicotyledonous weeds with further structure modification. Copyright © 2012 Society of Chemical Industry     

Influence of application volume on the efficacy of clodinafop-propargyl and fenoxaprop-P-ethyl on oats

The influence of application volume on the efficacy of clodinafop‐propargyl and fenoxaprop‐P‐ethyl on cultivated oats (Avena sativa) was studied in the glasshouse. Both herbicides were more efficacious when applied in 75 L ha^?1 than in 300 L ha^?1, with 11002 and 11006 nozzles respectively. However, when the same two volume rates were created by varying the speed of a 11003 nozzle, clodinafop‐propargyl efficacy was not affected by application volume, whereas fenoxaprop‐P‐ethyl remained more efficacious at 75 L ha^?1. This suggests that in the first experiment, fenoxaprop‐P‐ethyl efficacy was affected by changes in both spray quality and concentration, whereas only the former influenced clodinafop‐propargyl efficacy. The hypothesis that the fenoxaprop‐P‐ethyl formulation was more influenced by concentration than clodinafop‐propargyl was supported by dynamic surface tension studies and measures of active ingredient retention by oat plants. Within the practically relevant concentration range considered, surface activity of clodinafop‐propargyl remained low, with little influence on herbicide retention. In contrast, depending on the concentration, surface activity of fenoxaprop‐P‐ethyl was below or above levels that were critical for its retention. Although these differences may not be as apparent in the field as in the glasshouse, our study certainly indicates that both clodinafop‐propargyl and fenoxaprop‐P‐ethyl are herbicides favoured by low application volumes.     

Synthesis of 2-amino-6-oxocyclohexenylsulfonamides and their activity against Botrytis cinerea

BACKGROUND: With the objective of exploring the fungicidal activity of 2‐oxocyclohexylsulfonamides (2), a series of novel 2‐amino‐6‐oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo. RESULTS: The compounds were characterised by IR, ¹H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N‐(2‐methylphenyl)‐2‐(2‐methylphenylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (13) and N‐(2‐chlorophenyl)‐2‐(2‐chlorophenylamino)‐6‐oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC₅₀ values of 8.05 and 10.56 µg mL^?1 respectively. Commercial fungicide procymidone provided an EC₅₀ value of 0.63 µg mL^?1. The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ‐tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N‐cyclohexyl‐2‐(cyclohexylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone. CONCLUSION: The present work demonstrated that 2‐amino‐6‐oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea. Copyright © 2011 Society of Chemical Industry     

Factors affecting the seed germination and seedling emergence of muskweed (Myagrum perfoliatum)

Myagrum perfoliatum is a noxious broad‐leaved weed in western Iranian farming systems. A better understanding of the timing of seedling emergence would facilitate the development of better control strategies for this weed. Therefore, the objective of this study was to examine the effects of different factors on muskweed seed germination. Only 2.8% of the seeds of this species, which are encapsulated in siliques, germinated by, while the seeds that had been removed from the siliques had a 50% germination rate. The immersion of muskweed fruits in concentrated sulfuric acid for 110 min was the best treatment for promoting germination. Gibberellic acid stimulated the germination of the naked seeds by 29.1%, potassium nitrate (40 mmol L^‐1) increased the germination rate to 71%, while higher concentrations of potassium nitrate inhibited germination. The optimum germination temperature for the naked seeds was 20/10°C (day/night) and light was not required for germination. No seedling emerged when the seeds were buried 6 cm deep. The seeds were sensitive to both osmotic and salinity stress, but they germinated to 46–49% over a pH range of 4–10. The results of this study revealed that the seeds of M . perfoliatum have physiological dormancy and that it is slowly broken via after‐ripening. However, the fruit wall can prevent germination after physiological dormancy is broken. Thus, this species has the potential to form a persistent seed bank because of the presence of the fruit wall.     

Ethyl formate plus methyl isothiocyanate--a potential liquid fumigant for stored grains

BACKGROUND: Methyl bromide is being phased out for use on stored commodities, as it is listed as an ozone‐depleting substance, and phosphine is the fumigant widely used on grains. However, phosphine resistance occurs worldwide, and phosphine fumigation requires a long exposure period and temperatures of > 15 °C. There is an urgent requirement for the development of a fumigant that kills insects quickly and for phosphine resistance management. This paper reports on a new fumigant formulation of 95% ethyl formate plus 5% methyl isothiocyanate as an alternative fumigant for stored grains. RESULTS: The formulation is stable for at least 4 months of storage at 45 °C. A laboratory bioassay with the formulation showed that it controlled all stages of Sitophilus oryzae (L.), Sitophilus granarius (L.), Tribolium castaneum (Herbst), Rhyzopertha dominica (F.), Trogoderma variabile Ballion and Callosobruchus maculatus (Fabricius) in infested wheat, barley, oats and peas at 80 mg L^?1 for 5 days, and in canola at both 40 mg L^?1 for 5 days and 80 mg L^?1 for 2 days at 25 ± 2 °C. After an 8–14 day holding period, residues of ethyl formate and methyl isothiocyanate in wheat, barley, peas and canola were below the experimental permit levels of 1.0 and 0.1 mg kg^?1. However, fumigated oats needed an 18 day holding period. CONCLUSIONS: The findings suggest that the ethyl formate plus methyl isothiocyanate formulation has potential as a fumigant for the control of stored‐grain insect pests in various commodities. Copyright © 2011 Society of Chemical Industry     

Inheritance of resistance to fenoxaprop‐p‐ethyl in sprangletop (Leptochloa chinensis L. Nees)

Sprangletop (Leptochloa chinensis L. Nees) is a serious grass weed in direct‐seeded rice cropping systems in Thailand. One population of sprangletop, BLC1, was found to be resistant to fenoxaprop‐p‐ethyl at 62‐fold the concentration of a susceptible biotype, SLC1. This study elucidated the inheritance of resistance to fenoxaprop‐p‐ethyl in this sprangletop BLC1 genotype. The reaction to the herbicide at 0.12–2.4 mg ai L^?1 was determined in the seedlings of self‐pollinated resistant BLC1, susceptible SLC1 and SLC1 that had been allowed to cross‐pollinate with BLC1. At 0.24 mg ai L^?1, all the seedlings of SLC1 were killed, while 99% of BLC1 survived, along with 5% of the cross‐pollinated SLC1 seedlings, which were considered to be putative F₁ hybrids. The root and shoot lengths of the F₁ hybrids in 0.24 mg ai L^?1 of fenoxaprop‐p‐ethyl, relative to those in the absence of the herbicide, were close to or the same as the resistant parent, indicating that the resistance is a nearly complete to complete dominant trait. One‐hundred‐and‐forty‐one of the F₂‐derived F₃ families were classified by their response to the herbicide at 0.24 and 0.48 mg ai L^?1 into 39 homozygous susceptible : 72 segregating : 30 homozygous resistant, fitted with a 1:2:1 ratio at χ² = 1.21 and P = 0.56, indicating that the resistance to fenoxaprop‐p‐ethyl in the sprangletop BLC1 genotype is controlled by a single gene.     

Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti

BACKGROUND: An assessment was made of the toxicity of imperatorin and osthole identified in Cnidium monnieri fruit, 11 related compounds and five insecticides to larvae from insecticide‐susceptible Culex pipiens pallens (KS‐CP strain) and Aedes aegypti and wild C.p. pallens (YS‐CP colony) using a direct‐contact mortality bioassay. Results were compared with those of the conventional larvicide temephos. RESULTS: Imperatorin (LC₅₀ = 3.14 and 2.88 mg L^?1) was 1.9‐, 3.7‐ and 4.2‐fold and 2.4‐, 4.5‐ and 4.6‐fold more toxic than isopimpinellin, isoimperatorin and osthole against susceptible C. p. pallens and A. aegypti larvae respectively. Overall, all of the compounds were less toxic than temephos (0.011 and 0.019 mg L^?1). The toxicity of these compounds was virtually identical against larvae from the two Culex strains, even though YS‐CP larvae were resistant to fenthion (resistance ratio RR = 390), deltamethrin (RR = 164), cyfluthrin (RR = 14) and temephos (RR = 14). This finding indicates that the coumarins and the insecticides do not share a common mode of action. The structure–activity relationship indicates that the chemical structure and alkoxy substitution and length of the alkoxyl side chain at the C8 position are essential for imparting toxicity. CONCLUSION: The C. monnieri fruit‐derived coumarins and the related coumarins described merit further study as potential insecticides or lead molecules for the control of insecticide‐resistant mosquito populations. Copyright © 2012 Society of Chemical Industry     

Multifunctionalised benzoxazinones in the systems Oryza sativa–Echinochloa crus‐galli and Triticum aestivum–Avena fatua as natural‐product‐based herbicide leads

BACKGROUND: 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. RESULTS: 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 IC₅₀ 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 (IC₅₀ = 6 µM , r² = 0.9616). CONCLUSION: 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. Copyright © 2010 Society of Chemical Industry     

Effects of some chemical factors,prechilling treatments and interactions on the seed dormancy‐breaking of two Papaver species

Seed dormancy is a common strategy of many plants to survive in natural and agricultural ecosystems. This study examined the effects of some chemical factors, including gibberellic acid and potassium nitrate, the prechilling temperature, duration and conditions and the light regimes on the seed dormancy‐breaking of Papaver rhoeas L. and Papaver dubium L. The results showed that all the tested seed dormancy‐breaking treatments significantly stimulated the germination of the two Papaver species. The seed germination was significantly influenced in relation to the seeds that were treated with 0–1250 p.p.m. of gibberellic acid. The maximum germination was observed in P. rhoeas L. at 750 p.p.m. and in Pa. dubium L. at 500 p.p.m. in the light/dark regime. There was a significant increase in the germination with an increase in the potassium nitrate concentration. The greatest germination was achieved at the lowest potassium nitrate concentration (0.5 g L^?1) in the light/dark regime. The wet prechilling was more effective than the dry prechilling in the dormancy‐breaking of both P. rhoeas L. and Pa. dubium L. The highest germination percentage was found in the wet prechilling condition after 45 days' prechilling duration. The combination of gibberellic acid and potassium nitrate was more successful than their separate application in the stimulation of germination in both Papaver species. Among the combined treatments of prechilling and gibberellic acid, the highest germination of P. rhoeas L. was recorded in the seeds that were treated with wet prechilling for 45 days with 750 p.p.m. gibberellic acid, while in Pa. dubium L., the maximum germination was recorded with wet prechilling for 45 days with 500 p.p.m. of gibberellic acid.     

Effect of naringenin on the growth and lignin biosynthesis of gramineous plants

Lignin biosynthesis is essential for plant growth. 4‐Coumarate CoA ligase (4‐CL, EC6.2.1.12) is involved in the monolignol synthesis and occupies a key role in regulating carbon flow into the phenylpropanoid metabolism pathway. Naringenin, one of the metabolites in this pathway, is known as a potent in vitro inhibitor of 4‐CL. The growth of rice (Oryza sativa L. cv. Koshihikari), maize (Zea mays L. cv. Yellow corn) and Echinochloa oryzicola Vasing seedlings at the 2nd leaf stage was inhibited after continuous root application with 0.1 mmol L^?1 naringenin for 1 week, although naringenin did not kill these gramineous plants. The highest inhibition of fresh weight increase was observed in maize, followed by rice and E. oryzicola. The symptoms in these plants were root browning, delay of leaf/root development and shoot dwarfing. Naringenin treatment increased the contents of 4‐CL substrates, cinnamic acid, 4‐coumaric acid, caffeic acid and ferulic acid from 1.2 to 7.2 times and from 1.2 to 3.5 times in shoots and roots, respectively, except for ferulic acid in E. oryzicola roots. It also caused a slight decrease of the lignin content and alteration of lignin constitutions in rice plants. These results suggested that the monolignol pathways after 4‐CL towards lignin has the possibility to be the novel action sites of plant growth retardants, although further investigations are needed to clarify the mode of action.