Synthesis of new compounds related to the commercial fungicide tricyclazole

BACKGROUND: Tricyclazole is a commercial fungicide used to control rice blast. As part of re‐registration activities, samples of metabolites and process impurities are required. In addition, isotopically labeled tricyclazole samples are also required. RESULTS: Four new compounds related to tricyclazole are reported. An isotopically labeled sample of tricyclazole was prepared that contained two ¹⁵N atoms and one ¹³C atom. Radiolabeled tricyclazole with ¹⁴C at the triazole C3 position was also synthesized. A new process impurity in technical tricyclazole was identified and synthesized. A new metabolite of tricyclazole was identified, independently synthesized and characterized by X‐ray crystallography. CONCLUSION: A previously unreported metabolite of tricyclazole has been identified and structurally characterized. In addition, a new process impurity has been identified by independent synthesis. Identification of these new compounds has facilitated the continued registration of this important fungicide. Copyright © 2011 Society of Chemical Industry     

Changes in ide Leuciscus idus (L.) females’ reproductive parameters after stimulation with carp pituitary homogenate (CPH) and Ovopel: the effect of domestication?

Three groups (wild—WS, semi-pond—SPS, and pond-cultured—PS) of ide Leuciscus idus (L.) were examined. Each group consisted of 30 females and 10 males, aged 5–8 years. All groups were stimulated with two agents: carp pituitary homogenate (CPH) and a synthetic hormonal preparation Ovopel. The amount of ovulating females decreased in conjunction with females’ domestication level, mainly because of very low efficacy of CPH for pond-reared ide stimulation. The percentage of ovulating females stimulated with Ovopel (97.0 %) was significantly higher comparing to CPH (63.0 %). No significant differences were found in latency time between the groups but spawning synchronization increased in conjunction with ide domestication. The positive correlation between domestication level and latency time, i.e., the higher the domestication level, the higher the latency time, was stated. No significant differences were found in PGSI as well as in total volume of obtained eggs, but groups differed significantly in the number of dry eggs and in number of swollen egg. Significant negative correlation between domestication level and number of swollen eggs, i.e., the higher the domestication level, the lower the number of eggs, was detected. The survival rate at the eyed stage was the highest in WS group (60.4 %) and PS group (57.7 %), and was significantly higher than in SPS group (51.8 %). Eggs obtained after CPH stimulation had higher survival rate at the eyed-egg stage (60.3 %) than eggs obtained from the fish stimulated with Ovopel (53.0 %). The data suggest that some form of domestication appeared in ide cultivated for several generations in carp pond.     

Cuticular uptake of xenobiotics into living plants. Part 2: influence of the xenobiotic dose on the uptake of bentazone, epoxiconazole and pyraclostrobin, applied in the presence of various surfactants, into Chenopodium album, Sinapis alba and Triticum aestivum leaves

This study has determined the uptake of three pesticides, applied as commercial or model formulations in the presence of a wide range of surfactants, into the leaves of three plant species (bentazone into Chenopodium album L. and Sinapis alba L., epoxiconazole and pyraclostrobin into Triticum aestivum L.). The results have confirmed previous findings that the initial dose (nmol mm(-2)) of xenobiotic applied to plant foliage is a strong, positive determinant of uptake. This held true for all the pesticide formulations studied, although surfactant concentration was found to have an effect. The lower surfactant concentrations studied showed an inferior relationship between the amount of xenobiotic applied and uptake. High molecular mass surfactants also produced much lower uptake than expected from the dose uptake equations in specific situations.     

Volatile compounds in Spanish, French, and American oak woods after natural seasoning and toasting

The volatile composition (volatile phenols, phenolic aldehydes, furanic compounds, lactones, phenyl ketones, and other related compounds) of Spanish oak heartwood of Quercus robur, Quercus petraea,Quercus pyrenaica, and Quercus faginea was studied by gas chromatography/mass spectrometry, in relation to the processing in barrels cooperage and in relation to the French oak of Quercus robur (Limousin) and Quercus petraea (Allier) and American oak of Quercus alba (Missouri), which are habitually used in cooperage. The volatile composition of seasoned oak woods varied according to individual trees, species, and origins, and the differences were more significant in Spanish species with respect to American species than with respect to French species. The toasting process influenced the volatile composition of wood. It led to high increases in the concentration of volatile phenols, furanic aldehydes, phenyl ketones, and other related structures, but the effect on w-lactones levels depended on species and origin. The volatile composition in Spanish oak species evolved during toasting like in French and American oak, but quantitative differences were found, especially important in American species with respect to European species.     

Effects of prostaglandin F(2alpha) and nitric oxide on the secretory function of bovine luteal cells

The objective of the present study was to investigate the influence of prostaglandin F(2alpha) (PGF (2alpha)) and nitric oxide (NO) on production of steroids and PGs by culturing bovine luteal cells obtained from ovaries on days 8-12 of the estrous cycle with a nitric oxide (NO) donor (Spermine NONOate), and a NO synthase inhibitor (N(G)-nitro-L-arginine methyl ester dihydrochloride: L-NAME). When the cells were exposed for 24 h to PGF(2alpha) (10(-7)-10(-5) M), production of progesterone (P(4)) increased significantly at all doses used (P<0.05). Moreover, PGF(2alpha) stimulated PGF(2alpha) production (P<0.01), depressed testosterone (T) production (P<0.05), but did not affect synthesis of prostaglandin E(2) (PGE(2)). Spermine NONOate decreased P(4) production to 66%, 47% and 34% of the control concentration after treatment with 10(-5) M, 10(-4) M and 10(-3) M, respectively, but did not affect T production, and increased PGF(2alpha) synthesis (P<0.05) and PGE(2) (P<0.01) at all doses used. L-NAME increased production of P(4) (P<0.01) but did not affect (P>0.05) secretion of T, PGF(2alpha) and PGE(2). Estradiol-17beta (E(2)) was detectable on the level of sensitivity of assay and was not significantly altered by any treatments. The overall results suggest that PGF(2alpha) and NO produced locally in bovine CL play roles in the regulation of the secretory function of the bovine CL as auto/paracrine factors.     

Transmission by aphids of potato spindle tuber viroid encapsidated by potato leafroll luteovirus particles

Potato spindle tuber viroid (PSTVd) was transmitted by Myzus persicae to Physalis floridana from P. floridana plants that also were infected with potato leafroll luteovirus (PLRV), whereas it was not transmitted by aphids from plants infected with PSTVd alone. Dot-blot hybridisation was used to detect PSTVd. The results indicate that PLRV can assist PSTVd in its transmission by M. persicae. Doubly infected, aphid-inoculated P. floridana plants from the previous experiment were used as the source plants in aphid transmission tests to the tomato cv. Rutgers, P. floridana and Datura stramonium. PSTVd was detected in 17 of 30 plants of tomato. The viroid was not detected by dot-blotting in any plant of P. floridana and D. stramonium in this experiment, but it was recovered from some plants by sap inoculation of the Rutgers plants. Treatment with RNase A of PLRV preparations purified from doubly infected plants indicated that PSTVd was encapsidated by PLRV particles.     

Effect of light wavelength on growth and flowering of narcissi forced under short-day and low quantum irradiance conditions

Summary

Four narcissus cultivars were forced under artificial light using fluorescent lamps which emitted white (307 – 770 nm), blue (393 – 580 nm), red (540 – 760 nm), yellow (450 – 750 nm), or green (387 – 680 nm) light. The photosynthetic photon flux density was 12.5 μmol m^–2 s^–1, with a 6 h photoperiod. Light colour (wavelength) had no significant effect on flowering date, or on the number of flowers collected (P < 0.05). Narcissus bulbs exposed to blue light (393 – 580 nm) formed shorter, more rigid shoots of lower weight with 13 – 40% shorter leaves.     

The enzymes of glycogen and trehalose catabolism from Hysterothylacium aduncum (Nematoda: Anisakidae)

The activity of alpha-amylase, glucoamylase, maltase, trehalase, glycogen phosphorylase and trehalose phosphorylase was measured in extracts from larval and adult Hysterothylacium aduncum (Rudolphi, 1802), parasitic nematode of marine fish. The content of glycogen and trehalose in the worm's body was also determined. Both the hydrolytic and phosphorolytic paths of sugar decomposition are present in H. aduncum. In the larvae glycogen was utilised mainly via the hydrolytic path. In the adults the activities of phosphorolytic enzymes were higher than in the larvae. In both stages the activity of trehalose phosphorylase is present. In adult nematodes it is uncommonly high. The dominating sugars in the adults were glucose and glycogen, while in the larvae it was trehalose.     

Effect of coniferyl alcohol addition on removal of chlorophenols from water effluent by fungal laccase

The effect of coniferyl alcohol on removal of chlorinated phenols from a water environment byRhizoctonia praticola andCerrena unicolor laccases was studied. At optimal conditions in which 7 mM coniferyl alcohol and laccase were added to chlorinated phenols over 20h, about 34% of the radioactivity of 4-chlorophenol, 57% of 2,4-dichlorophenol, 66% of 2,4,5-trichlorophenol, and 85% of pentachlorophenol were removed from the supernatants, compared to the level without laccase activity. After 12-h incubation periods at the optimal concentrations of coniferyl alcohol and laccase (added simultaneously), the fast first phase of chlorophenol removal was complete in 1 h, and eventually coniferyl alcohol enhanced the removal of 4-chlorophenol by 40%, 2,4-dichlorophenol by 54%, 2,4,5-trichlorophenol by 60%, and pentachlorophenol by 76%.     

Evaluation of susceptibility of auto- and alloplasmic barley DH lines to Fusarium seedling blight

Auto- and alloplasmic doubled haploid (DH) lines of barley were examined for susceptibility to Fusarium culmorum (W.G.Sm.) Sacc. (isolate KF350) seedling blight. Inoculated kernels were incubated at 20 °C in a chamber saturated to 100% RH a with 12/12 h dark/light cycle. Germination capacity, disease score on a 5-degree scale and root length were evaluated. The data were analysed statistically using three-factor analysis of variance. It was observed that the infection score of roots of DH lines with H. bulbosum cytoplasm was higher than that of their autoplasmic analogues. Length of infected seedling roots expressed as per cent of the control root length ranged from 81 to 56% in autoplasmic DH lines and from 60 to 48% in alloplasmic lines. These differences were statistically significant (at P = 0.01). It was evident, that H. bulbosum cytoplasm increase susceptibility of barley genotypes to Fusarium seedling blight.