Simetryn

Preparation and application of simetryn-imprinted nanoparticles in triazine herbicide residue analysis

This work provides a simple and rapid method for synthesis uniform simetryn imprinted nanoparticles, which can be used to pretreat the tested samples before detecting. A series of computational approach were employed for design simetryn-imprinted polymer. Based on the conclusion of theoretical calculation, the simetryn imprinted nanoparticles were synthesized using simetryn as template, methacrylic acid as monomer with different solvent volume and synthesis conditions. The obtained nanoparticles have small size, uniform distribution and high imprinted factor. Scatchard analysis and quantum chemical calculations were applied for evaluating the interaction of simetryn with methacrylic acid in the imprinting process. The selectivity and recognition ability of the simetryn imprinted nanoparticles for six triazine herbicides and two other type herbicides were investigated. The results show that the simetryn imprinted nanoparticles had high selectivity and binding capacity and could be used for the separation and enrichment of four triazine pesticide residues from actual samples. A method of molecularly imprinted matrix solid phase extraction ultra-performance liquid chromatography tandem mass spectrometry was established for detecting four kinds of triazine herbicide residues in tobacco. The recovery rate of terbuthylazine, simetryn, atrazine, and prometryn in tobacco was 84.03-119.05%, and the relative standard deviation was 0.35-10.12%.

Behavior of simetryn and thiobencarb in the plough zone of rice fields

The behavior of simetryn and thiobencarb in flooded rice soil was investigated in a 2-year study. The concentrations of simetryn and thiobencarb were in the hundreds of μg kg?1 in the top soil layer (0–5 cm) and became significantly lower in tens of μg kg?1 in the deeper soil layers (5–10 and 10–15 cm). The half-lives of the two herbicides were also shorter (36 and 17 days for simetryn and thiobencarb, respectively) in the top soil layer, as they were most affected by environmental conditions, compared with corresponding values of 82 and 69 days in the 5–10 cm soil layer. Simetryn concentration was stable, while thiobencarb’s half-life was 165 days in the 10–15 cm layer. About 35% of the applied mass of simetryn and thiobencarb were found in the rice soil compartment.

A molecularly imprinted polymer with integrated gold nanoparticles for surface enhanced Raman scattering based detection of the triazine herbicides, prometryn and simetryn

A class-specific molecular imprinted polymer (MIP) is described for simultaneous recognition of prometryn and simetryn prior to their determination via a fingerprint signal (at 974 cm^-1 and 1074 cm^-1) in the surface enhanced Raman scattering (SERS) spectra that were acquired in the presence of gold nanoparticles. The imprinted nanoparticles were applied to the analysis of rice and wheat samples spiked with both herbicides. The method has fairly good recoveries (72.7-90.9%) with a relative standard deviation of 1.7-7.8%, and a 20 μg·kg^-1 limit of detection. The imprint factors (compared to non-imprinted polymers) are 5.3 for prometryn and 4.2 for simetryn (both at 10 μg·mL^-1 of the initial solution). Graphical abstract A MIP-SERS method was developed for simultaneous detection of triazine herbicides (prometryn and simetryn) in food samples.

Application of an amphibian (Silurana tropicalis) metamorphosis assay to the testing of the chronic toxicity of three rice paddy herbicides: simetryn, mefenacet, and thiobencarb

We examined the chronic toxicity of three rice paddy herbicides (simetryn, mefenacet, and thiobencarb) using an amphibian (Silurana tropicalis) metamorphosis assay (a 28-day semistatic test under an individual-separated exposure system). Each herbicide was tested at two concentrations (1/100 and 1/10 of the 96-h LC50 value reported previously) with morphometric, gravimetric, and thyroid-histological endpoints. Simetryn caused significant retardation in growth and development at both test concentrations (0.04 and 0.40mg/L), as indicated by significantly shorter total body lengths and hind limb lengths, smaller wet body masses, and delayed developmental stages compared to those observed in the control tadpoles. However, no clear histopathology was observed in the thyroid glands of the tadpoles exposed to simetryn. These results suggest that simetryn can act as a chemical stressor retarding tadpole growth and development without disrupting thyroid functions, even at 1/100 of the 96-h LC50 value. In addition, scoliosis near the tail base was observed in the tadpoles exposed to 0.40mg/L of simetryn at a significantly high incidence (7/30=23.3%). Therefore, simetryn can also act as a teratogen inducing axial malformations at 1/10 of the 96-h LC50 value. During the 28 days of exposure, neither mefenacet (0.03 and 0.30mg/L) nor thiobencarb (0.008 and 0.080mg/L) induced any abnormalities, although the test concentrations measured immediately before the solution renewals decreased to nearly 50 percent of the nominal concentrations since day 14. Because the concentrations tested for simetryn are likely to occur in paddy water, wild anuran tadpoles in paddy water may therefore be adversely impacted by simetryn.

Acute toxicity of rice paddy herbicides simetryn, mefenacet, and thiobencarb to Silurana tropicalis tadpoles

I examined the toxicity of rice paddy herbicides simetryn, mefenacet, and thiobencarb to amphibians by conducting acute toxicity tests with tadpoles of Silurana tropicalis, which has attracted as a new model species instead of Xenopus laevis. The tadpoles at stages 49 and 50 were exposed to the herbicides at several concentrations during 96 h, and median lethal concentration (LC50) values were calculated at 24-h intervals. The LC50 values of simetryn, mefenacet, and thiobencarb were 16.9-3.70 mg/L (79.3-17.4 microM), 3.06-2.70 mg/L (10.3-9.04 microM), and 1.77-0.752 mg/L (6.85-2.92 microM), respectively. The most toxic herbicide was thiobencarb followed by mefenacet and simetryn. As for thiobencarb, the sensitivity of S. tropicalis was similar to that of X. laevis reported previously. This suggests that S. tropicalis as well as X. laevis can act as a model species in acute toxicity tests. The LC50 values of the three herbicides were very close to or at most two orders of magnitude higher than the maximum concentrations likely to occur in paddy water. Therefore, the three herbicides can be harmful to amphibian larvae living in paddy water.