Carane-3,4-diol Derivatives as Potential Water-Based Herbicides.

Twelve novel carane-3,4-diol derivatives were designed, synthesized, and evaluated for their herbicidal activities against Lolium multiflorum Lam. and Brassica campestris for the first time. The relationships between the chemical structural factors, including types, the number or the carbon chain length of functional groups, associated with the lipophilicity and the herbicidal activity of the tested compounds were also discussed. The results showed that most of newly synthesized compounds had a dose-dependent, herbicidal activity against the root and shoot growths of Lolium multiflorum Lam. and Brassica campestris. Compared to carane-3,4-diol, most of the target derivatives possessed improved lipophilicity and certain solubilities in representative solvents with different polarities. Particularly, ester derivatives 3a-3b and 3e can be dissolved or dispersed in water, but also displayed higher herbicidal activity against Lolium multiflorum Lam. and Brassica campestris than other ester derivatives. The 50 % inhibitory concentration (IC50) value of compound 3e against shoot growth of Brassica campestris (0.485 mmol/L) was superior to that of commercial herbicide glyphosate (1.14 mmol/L), indicating that the potential application as a water-based herbicide for Brassica campestris control.

Longifolene-Derived Primary Amine Carboxylates for Sustainable Weed Management: Synthesis and Herbicidal Activity.

Twelve novel longifolene-derived primary amine carboxylates were synthesized and evaluated for herbicidal activity. The structures of title compounds were confirmed by Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry. The results showed that all the synthesized compounds exhibited higher herbicidal activity than the corresponding carboxylic acids involved in the reaction and the commercial herbicide glyphosate; some of them even possessed inhibition rates of 100% against Lolium multiflorum Lam. and Brassica campestris at low concentrations (0.039-0.313 mmol/L). Moreover, structural factors, including types of carboxylates and carbon chain length, had a great influence on the herbicidal performance. The herbicidal activity of dicarboxylates was similar to or much higher than that of corresponding monocarboxylates and glyphosate. Furthermore, compound 5l was found to be the most active candidate against the root and shoot growth of L. multiflorum Lam. and B. campestris with half maximal inhibitory concentrations (IC50) of around 0.010 and 0.023 mmol/L. The present work indicated that those prepared compounds have great potential to serve as high-performance botanical herbicides used at low doses.

Highly Effective and Broad-Spectrum Antimicrobial Quaternary Ammonium Salts Containing Camphene Structure: Preparation, Surface-Active Properties, and Bioassay.

A series of novel quaternary ammonium salts (QASs) (4a-4n) comprising a camphene moiety were synthesized for the first time. Fourteen examples were prepared from camphene through Prins reaction, halogenation, and quaternarization, successively. The structures of the synthesized QASs were analyzed by Fourier transform infrared spectroscopy, 1H NMR, 13C NMR and high-resolution mass spectrometry. Surface-active properties, emulsifying abilities, and foaming properties of the investigated compounds were then studied. The antimicrobial activities of these QASs against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae), and fungi species (Candida albicans, Candida tropicalis, and Aspergillus niger) were determined by the microdilution method. The results showed that the chemical structural factors, including types of substitutes and alkyl chain length, might be correlated with the lipid-water partition coefficient (cLog P), which played a critical role in the antimicrobial process. Compounds with alkyl chain lengths (N) in the range of 10-14 were relatively more active, while compounds bearing pyridinium, benzyl, methylimidazolium groups, or varied alkyl chain lengths (N < 5 and N > 16) were almost inactive. Compound 4k possessing a dodecyl group exhibited the most effective and broad-spectrum antimicrobial activity against almost all tested bacteria and fungi with the minimal inhibitory concentration values ranging from 0.24 to 0.98 µg/mL.

(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,-9,10,10a-octa-hydro-phenanthren-1-yl)-methanaminium 4-toluene-sulfonate.

In the title compound, C(20)H(32)N(+)·C(7)H(7)O(3)S(-), the configurations of the two chiral centers observed in the protonated cation are consistent with previous reports. In the crystal structure, weak inter-molecular N-H⋯O hydrogen bonds link ions into chains which develop along the a axis. The isopropyl group and four CH groups of the attached benzene ring are disordered approximately equally over two positions.