Activity of the botanical aphicides 1,5‐diphenyl‐1‐pentanone and 1,5‐diphenyl‐2‐penten‐1‐one on two species of Aphididnae

1,5‐Diphenyl‐1‐pentanone (A) and 1,5‐diphenyl‐2‐penten‐1‐one (B) are natural products extracted for the first time from Stellera chamaejasme. Laboratory bioassay showed that the two products have strong contact activity and very good anti‐feedant activity against Aphis gossypii and Schizaphis graminum. Both products showed dose‐dependent relationships for both forms of activity against the two aphids, the contact activity of B being about twice that of A. Both products were inferior to methomyl in contact activity but superior in anti‐feedant activity against the two aphids. This is the first report of aphicidal activity in these two compounds, which may represent a new class of aphicide. © 2001 Society of Chemical Industry     

Synthesis and fungitoxic activity of 5‐aryl‐1‐formyl‐4,5‐dihydro‐3‐(2‐hydroxyphenyl)‐1H‐pyrazoles and their complexes

Cyclization of 3‐aryl‐1‐(2‐hydroxyphenyl)prop‐2‐en‐1‐ones with hydrazine hydrate in refluxing formic acid afforded the title ligands, 5‐aryl‐1‐formyl‐4,5‐dihydro‐3‐(2‐hydroxyphenyl)‐1H‐pyrazoles (HL¹–HL⁴, Ar = Ph, 4‐CH₃O‐C₆H₄‐, 2‐furyl, 2‐thienyl). Reaction of HL¹–HL⁴ with the divalent metal ions, Mn²⁺, Co²⁺, Ni²⁺, Cu²⁺, and Zn²⁺, afforded novel complexes of the type [ML₂] (M = metal ion; L = deprotonated ligand) which were characterized by elemental analyses, molecular weight determinations, molar conductances, magnetic moments and electronic and infrared spectral data. The ligands behaved as tridentate, coordinating through the phenolic oxygen after deprotonation, N‐2 of the pyrazole ring and oxygen of the 1‐formyl group. The ligands and their complexes were evaluated for growth‐inhibiting activity against four phytopathogenic fungi. Macrophomina phaseoli was generally most sensitive followed by Alternaria alternata and Colletotrichum falcatum while Fusarium oxysporum was least sensitive to the tested compounds. The ligand HL¹ and its complexes showed the best activity against the fungi tested. © 2000 Society of Chemical Industry     

Surfactant‐induced deposit structures in relation to the biological efficacy of glyphosate on easy‐ and difficult‐to‐wet weed species

BACKGROUND: Typical active ingredient (AI) residue patterns are formed during droplet drying on plant surfaces owing to the interaction of spray solution characteristics and leaf micromorphology. Currently, comparatively little is known about the influence of AI deposit patterns within a spray droplet residue area on the penetration and biological efficacy of glyphosate. A scanning electron microscope with energy dispersive X‐ray microanalysis has been used to characterise residue patterns and to quantify the area ultimately covered by glyphosate within the droplet spread area. RESULTS: The easy‐to‐wet weed species Stellaria media L. and Viola arvensis L., as well as the difficult‐to‐wet Chenopodium album L. and Setaria viridis L., differing in their surface micromorphology, have been used. Rapeseed oil ethoxylates (RSO 5 or RSO 60) were added to glyphosate solutions to provide different droplet spread areas. Addition of RSO 5 enhanced droplet spread area more than RSO 60, and both caused distinct glyphosate residue patterns. The biological efficacy of treatment solutions showed no significant correlation with the area ultimately covered by glyphosate. CONCLUSION: The results have implications on herbicide uptake models. This study shows that droplet spread area does not correspond to the area ultimately covered by glyphosate, and that the latter does not affect glyphosate phytotoxicity. Copyright © 2009 Society of Chemical Industry     

Improvement of the desorption of the pesticide 2,4‐D via complexation with HP‐β‐cyclodextrin

Inclusion complex formation of 2,4‐dichlorophenoxyacetic acid (2,4‐D) with hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD) has been proposed as a way of modifying the behaviour of the pesticide in the soil environment. The present study assesses the effect of complex formation on 2,4‐D physicochemical properties (aqueous solubility, crystallinity and dissolution rate) and its behaviour on soils. The solid complexes were prepared using different methods (spray drying, kneading and heating in a sealed container). To confirm the complex formation in the solid state differential scanning calorimetry, hot stage microscopy and x‐ray diffraction techniques were employed. Complex formation in solution was studied by phase solubility. The presence of HP‐β‐CD increased the 2,4‐D solubility nine times approximately. The apparent stability constant was determined as 98.6 M ⁻¹. The dissolution rates of the 2,4‐D/HP‐β‐CD complexes were examined and compared with that of the pure pesticide. The results indicated that the complex may have great utility as a rapid way of dissolving the pesticide. Batch experiments were performed to study the adsorption–desorption of 2,4‐D on soils and the influence of the HP‐β‐CD over these processes. The results showed that HP‐β‐CD could increase the desorption of 2,4‐D previously adsorbed on soils. © 2000 Society of Chemical Industry     

Phototransformation of metoxuron [3‐(3‐chloro‐4‐methoxyphenyl)‐1,1‐dimethylurea] in aqueous solution

UV irradiation of metoxuron in aerated aqueous solution at 254 nm or between 300 and 450 nm led initially to an almost specific photohydrolysis of the C–Cl bond, resulting in the formation of 3‐(3‐hydroxy‐4‐methoxyphenyl)‐1,1‐dimethylurea (MX3) and hydrogen chloride. The quantum yield was determined to be 0.020 (±0.005) in solutions irradiated at 254 nm. Five minor photoproducts were also identified, in particular the dihydroxydimethoxybiphenyl derivatives resulting from the phototransformation of MX3. Irradiation increased the toxicity of an aqueous solution of metoxuron to the marine bacterium Vibrio fischeri. © 2001 Society of Chemical Industry