Synthesis, Herbicidal Activity, and Structure-Activity Relationships of O-Alkyl Analogues of Khellin and Visnagin.

Khellin and visnagin furanochromones were recently reported as potential new bioherbicides with phytotoxic activities comparable to those of some commercially available herbicides. In this study, we examined the effect of O-alkylation and O-arylalkylation of both khellin and visnagin on its effect on herbicidal and antifungal activity. Synthetic analogues included O-demethyl khellin and visnagin, acetylated O-demethyl khellin and visnagin, O-benzylated demethyl khellin and visnagin, four O-demethyl alkylated khellin analogues, and six O-demethyl alkylated visnagin analogues, many of which are reported here for the first time. Both acetate analogues of khellin and visnagin indicated more activity as herbicides on Lemna pausicostata than visnagin, with IC50 values of 71.7 and 77.6 µM, respectively. Complete loss of activity for all O-alkyl analogues with a carbon chain length of greater than 14 carbons was observed. The O-demethyl butylated visnagin analogue was the most active compound with an IC50 of 47.2 µM against L. pausicostata. O-Demethyl ethylated analogues of both khellin and visnagin were as effective as khellin. In the antifungal bioautography bioassay against Colletotrichum fragariae at 100 µg, the only active O-alkyl and O-arylalkyl analogues were O-ethylated, O-butylated, and O-benzylated visnagin analogues with zones of inhibition of 10, 9, and 9 mm, respectively, an effect comparable to that of visnagin and khellin.

Melissa officinalis L. as a Sprout Suppressor in Solanum tuberosum L. and an Alternative to Synthetic Pesticides.

The goal of this research was to screen plant essential oils (EOs) as sprout inhibitors or suppressors in potato (Solanum tuberosum L.). Three controlled environment experiments were conducted to screen 18 EOs and several pure compounds as sprout inhibitors. The EOs were applied using the wicked method on potato cv. Gala in 19 L plastic containers. The results indicated that Melissa officinalis L. EO inhibited sprouting, while Coriandrum sativum L. seed oil and the EO blend of Lavandula angustifolia Mill. and Salvia sclarea L. suppressed sprouting. The EOs of interest were analyzed using gas chromatography coupled to mass spectrometry (GC-MS) and/or a flame ionization detector (GC-FID); the detailed chemical profiles are provided. The M. officinalis EO was fractionated into seven fractions, and these were tested on minitubers. We identified two fractions (F and A) that suppressed potato sprouting better than the whole oil. The GC-MS-FID analyses of M. officinalis EO fraction A identified myrcene, Z-ocimene, E-ocimene, trans-caryophyllene, and α-humulene as the main constituents, while the main constituents of fraction F were α-terpineol, ß-citronellol, and geraniol. The pure isolated compounds, together with the major compound in M. officinalis EO (citral), were tested for sprout suppression on three potato cultivars (Ranger Russet, Terra Rosa, and Dakota TrailBlazer), which revealed that ß-citronellol reduced the sprout length and the number of sprouts in all three cultivars, while citral and (+)-α-terpineol reduced the sprout length and the number of sprouts in Ranger Russet relative to the two controls in all three cultivars. Myrcene had a stimulating effect on the number of sprouts in Cv. Terra Rosa. However, none of the pure compounds suppressed sprouting completely or were comparable to the EO of M. officinalis.

Biting deterrency of undecanoic acid and dodecanoic acid ester analogs against Aedes aegypti.

BACKGROUND: Mosquitoes remain one of the most significant threats to the health of humans throughout the world. This study was designed to evaluate the biting deterrent effects of a series of ester analogs of undecanoic acid (C:11:0) and dodecanoic acid (C:12:0) against Aedes aegypti (L), (Diptera: Culicidae), the yellow fever mosquito, using Klun and Debboun (K&D) and Ali and Khan (A&K) bioassay systems. RESULTS: In the K&D bioassays, C:11:0 esters methyl undecanoate, propyl undecanoate, butyl undecanoate, and pentyl undecanoate, and the C:12:0 esters methyl dodecanoate, ethyl dodecanoate, propyl dodecanoate, octyl dodecanoate, and dodecyl dodecanoate were most active. All of these esters were as effective as N,N-diethyl-m-toluamide (DEET) and as effective as the parent acids undecanoic acid and dodecanoic acid with biting deterrence index values ranging from 0.80 to 0.99. In the in vitro A&K bioassay undecanoic acid with a minimum effective dose (MED) of 3.125 µg cm-2 was the most active compound and showed higher activity than DEET (MED of 25 µg cm-2 ). The most active synthetic analog was butyl undecanoate with a MED of 12.5 µg cm-2 . The next most active analogs are the methyl ester analogs methyl undecanoate and methyl dodecanoate, both with MED values of 25 µg cm-2 . CONCLUSION: Fatty acid synthetic esters and structural analogs are a promising source of new mosquito repelling compounds and should be investigated further. Published 2020. This article is a U.S. Government work and is in the public domain in the USA.