To explore the influence of the positions of the two nitrogen atoms on the thiazole ring and the isoxazoline ring on the activity, a series of novel piperidyl thiazole derivatives containing oxime ether and oxime ester moieties with two nitrogen atoms on the same or opposite sides have been designed, synthesized, and first evaluated for their fungicidal activities against Phytophthora capsici in vitro. The bioassay results showed that the target compounds possessed moderate to good fungicidal activities against P. capsici, among which oxime ether compound 11b shows the highest fungicidal activity in vitro (EC50 = 0.0104 μg/mL) which is higher than dimethomorph (EC50 = 0.1148 μg/mL) and diacetylenyl amide (EC50 = 0.040 μg/mL). Compared with oxime ether compounds (the two nitrogen atoms are on the opposite sides), the activities of oxime ester compounds were significantly reduced. It is different from the commercial fungicide fluoxapiprolin, and the activities of the compounds with the two nitrogen atoms on the same side were significantly reduced compared to the compounds with the two nitrogen atoms on the opposite sides. Moreover, compounds 11b, 11d, 11e, and 11g showed moderate to good antifungal activities in vivo against Phytophthora capsici, Pseudoperonospora cubensis, and Phytophthora infestans. Scanning electron microscopy of compound 11b on the hyphae morphology showed that compound 11b might cause mycelial abnormalities of P. capsici.
Three new highly brominated polyphenols, 1-3, together with one known bromophenol, 4, were isolated from the EtOH extract of a marine red alga Symphyocladia latiuscula collected from the coast of Qingdao, P. R. China. Their structures were identified by extensive spectroscopic experiments (NMR and MS) and comparison with literature data. Compounds 3 and 4 showed activities against the Candida albicans with the MIC values of 25 and 12.5 μg/ml, respectively.
Chemical investigation of a Chinese collection of marine red alga Symphyocladia latiuscula yielded two new highly brominated phenols. The structures of the new compounds were elucidated by detailed spectroscopic analysis, including HRMS, 1D and 2D NMR and MS methods. Compounds 1 and 2 were evaluated for radical scavenging capability by 1,1-diphenyl-2-picrylhydrazuyl (DPPH) radical with the IC50 value of 14.5 and 20.5 μg/mL, respectively.
Song plays a vital role in communication in songbirds, primarily for territorial defense and mate attraction. Larger animals, having larger vocal organs, produce low sound frequencies more efficiently. Accordingly, the frequency of vocalizations is often negatively correlated with body size across species, and also among individuals of many species, including several nonsongbirds. However, little is known about whether song frequency reveals information about body size among males. We tested for the predicted positive relationship between body size and song traits in male dusky warblers (Phylloscopus fuscatus). In many animal species, some vocalizations are difficult to produce and can therefore indicate quality of signalers. Male dusky warblers produce songs with trilled sequences that are limited in their timing and frequency structure by physiological constraints on vocal performance. We investigated whether there was a relationship between body size and trilled vocalizations in the dusky warbler. We recorded songs of free-living male dusky warblers at dawn, and captured birds with mist nets for morphometric measurements (tarsus length, as an indicator of body size). We conducted correlation analyses between tarsus length and a composite measure of songs. In dusky warblers, body size was not significantly related to the average frequency of their overall songs, low frequency, bandwidth frequency, average note number of songs, or average song duration. In contrast, the maximum frequency of song was found to correlate positively with tarsus length. For trilled vocalizations, we found most trill traits were not significantly related to body size, and only the maximum frequency of trills was positively related to body size. Additionally, the maximal value of frequency bandwidth decreased with increasing trill rates. Overall, these results suggest that in male dusky warblers, the maximum frequency of the entire song is a reliable indicator of body size.
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