Metolachlor properties

The documented occurrence of pesticides in surface water is indicative that mnoff is an important pathway for transport of pesticide away from the site of appHcation. An estimated 160 t of atra2ine, 71 t of sima2ine, 56 t of metolachlor, and 18 t of alachlor enter the Gulf of Mexico from the Mississippi River annually as the result of mnoff (47). Field appHcation of pesticides inevitably leads to pesticide contamination of surface mnoff water unless mnoff does not occur while pesticide residues remain on the surface of the soil. The amount of pesticides transported in a field in mnoff varies from site to site. It is controUed by the timing of mnoff events, pesticide formulation, physical—chemical properties of the pesticide, and properties of the soil surface (48). Under worst-case conditions, 10% or more of the appHed pesticide can leave the edge of the field where it was appHed. 

The method using GC/MS with selected ion monitoring (SIM) in the electron ionization (El) mode can determine concentrations of alachlor, acetochlor, and metolachlor and other major corn herbicides in raw and finished surface water and groundwater samples. This GC/MS method eliminates interferences and provides similar sensitivity and superior specificity compared with conventional methods such as GC/ECD or GC/NPD, eliminating the need for a confirmatory method by collection of data on numerous ions simultaneously. If there are interferences with the quantitation ion, a confirmation ion is substituted for quantitation purposes. Deuterated analogs of each analyte may be used as internal standards, which compensate for matrix effects and allow for the correction of losses that occur during the analytical procedure. A known amount of the deuterium-labeled compound, which is an ideal internal standard because its chemical and physical properties are essentially identical with those of the unlabeled compound, is carried through the analytical procedure. SPE is required to concentrate the water samples before analysis to determine concentrations reliably at or below 0.05 qg (ppb) and to recover/extract the various analytes from the water samples into a suitable solvent for GC analysis. 

A Comparative Study of the Relationships Between the Mobility of Alachlor, Butylate, and Metolachlor in Soil and Their Physicochemical Properties... 

The order of the mobilities of alachlor, butylate, and metolachlor in columns of various soils was metolachlor > alachlor > butylate. This correlates directly with the water solubilities and inversely to the adsorption coefficients and octanol/water partition coefficients of these compounds. Diffusion of these compounds in soil thin-layers was as follows butylate > alachlor > metolachlor, which correlates directly with the vapor pressures of these compounds. Significant soil properties affecting diffusion appeared to be bulk density and temperature. Soil moisture is also probably important, but its effect on the diffusion of these compounds was not determined. 

Figure 1. Chemical properties of Alachlor, Butylate, and Metolachlor.

The good correlation of the results of vapor diffusion and leaching experiments for butylate, alachlor, and metolachlor with their physical properties has given support to the value of physical property measurements to predict pesticide movement in the soil. 

When it became clear that the two IS-enantiomers of metolachlor were responsible fijr most of the biological activity (see Fig. 1), there was the obvious challenge of finding a chemically and economically feasible production process for the active stereoisomers. Many methods allow the enantioselective synthesis of chiral molecules (that is the preferential formation of one enantiomer instead of the usual racemate). However, the selective preparation of S-metolachlor was a formidable task, due to the very special structure and properties of this molecule and also because of the extremely efficient production process for the racemic product as described above. During the course of the development efforts, the following minimal requirements evolved for a technically viable catalytic system ee S80%, substrate to catalyst ratio (s/c) >50 000 and turnover fi-equency (tof) >10 000 h" . 

A new active substance of the chloroacetanilide herbicide group, previously known by the code number CGA 24 705, is metolachlor, 2-chloro-6 -ethyl-N-(2-methoxy-l-methylethyl)-o-acetotoluidide (metolachlor, 18), the herbicidal properties of which have been described by Gerber el al. (1974). 

The use of benoxacor with (S)-metolachlor is particularly necessary under stress conditions for maize. Injury to corn from (S)-metolachlor is greater under cool or wet soil conditions [6-8] where both the availability of the herbicide may be increased and the ability of maize to metabolize metolachlor reduced [9]. Benoxacor and metolachlor have similar chemical properties, influencing there behavior in soil, and this tends to ensure that the safener and herbicide are taken up together, hence providing safening under various weather conditions. 

Al ough alachlor is no longer used in the U.S., the three chemical compounds have very similar structural (Figure 1) and chemical properties. Alachlor degradataion data may be useful as a model for this chemical class. Caution must be used in interpolating these data however since the ESA metabolite of metolachlor is formed more slowly and at lower concentrations in soil (18). The objective of this study was to compare atrazine and alachlor sorption, mineralization, and degradation potential, processes that are major contributors to the environmental fate of pesticides, from surface soil to aquifer sediments in laboratoiy studies. In addition, ctegradation of alachlor was compared under aerobic and anaerobic conditions. 

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