Thiamethoxam at normal and double the recommended use rate effectively controlled aphids, whiteflies and Helicoverpa, as the insect population decreased to a minimum within 10 days of spraying in comparison with the control. There was no significant difference between the two rates of application, and both thiamethoxam treatments significantly increased tomato fruit yield compared with the untreated control. A maximum residue limit (MRL) of 0.05 mg kg(-1) for tomato has been proposed, with a corresponding preharvest interval (PHI) of 8 days. These parallel advances in toxicology and analytical chemistry have strengthened the observations that thiamethoxam can be used safely and efficiently in crop protection programmes.
A laboratory experiment was conducted to study the stability of sulfosulfuron [1-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2yl) urea] in a controlled environment of pH, temperature, solvent, and surface. In another experiment the photostability of sulfosulfuron was studied after irradiation under sunlight. Under alkaline condition, it yielded 1-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl-3-(4,6-dimethoxypyrimidin-2-yl) amine, and under acidic condition it degraded to 1-(2-ethylsulfonylimidazo[1,2-a] pyridin)-3-sulfonamide and 4,6-dimethoxy-2-aminopyrimidine. Photodegradation included breaking of a sulfonylurea bridge, as in the case of acidic hydrolysis and contraction of the sulfonylurea bridge was the major pathway of alkaline hydrolysis.
The degradation of thiamethoxam [(EZ)-3-(2-chloro-1,3-thiazol-5-yl-methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene (nitro) amine] insecticide in buffers at different pH and temperature levels was investigated in laboratory studies. Acidic hydrolysis under conventional heating conditions and alkaline hydrolysis under both conventional heating and microwave conditions were carried out. Different hydrolysis products were found to form under alkaline and acidic conditions. Hydrolysis of thiamethoxam in acidic, neutral and alkaline buffers followed first-order reaction rate kinetics at pH 4, 7 and 9.2, respectively. Thiamethoxam readily hydrolyzed in alkaline buffer but was comparatively stable in neutral buffer solution. The main products formed under different conditions were characterized on the basis of infrared (IR), (1)H-NMR and Mass spectroscopy. The possible mechanisms for the formation of these hydrolysis products have also been proposed.
The metabolism of thiamethoxam [(EZ)-3-(2-chloro-1,3-thiazol-5-yl-methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene (nitro) amine] was investigated in whole plant, callus, and heterotrophic cell suspension culture of aseptically and field grown tomato (Lycopersicon esculentum Mill.) plants. The structure of the metabolites was elucidated by chromatographic (HPLC) and spectroscopic (IR, NMR, and MS) methods. Thiamethoxam metabolism proceeded by the formation of a urea derivative, a nitroso product, and nitro guanidine. Both urea and nitro guanidine metabolites further degraded in plants, and a mechanism has been proposed. In the plant, organ-specific differences in thiamethoxam metabolism were observed. Only one metabolite was formed in whole plant against four in callus and eight metabolites in cell suspension culture under aseptic conditions. Out of six metabolites of thiamethoxam in tomato fruits in field conditions, five were similar to those formed in the cell suspension culture. In the cell suspension culture, thiamethoxam degraded to maximum metabolites within 72 h, whereas in plants, such extensive conversion could only be observed after 10 days.
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