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<p>Acetochlor Registration Partnership (ARP)<br />
Represented by ZENECA Ag Products <br />
Western Research Center,<br />
1200 South 47th Street,<br />
Box 4023,<br /> 
Richmond CA 94804-0023<br /> 
(Tel: 510-231-1178)</p>

<h2>THE DETERMINATION OF ACETOCHLOR<br />
(N-(ETHOXYMETHYL)-2-CHLORO-2-ETHYL-6'- METHYLACETANILIDE) IN WATER </h2>

<h3>SCOPE:</h3>

<p>The analytical method described is suitable for the determination of residues of
the herbicide acetochlor (Surpass <sup> TM </sup> or Harness <sup> TM </sup>) in
water. The limit of quantitation (LOQ) for acetochlor using this method is 0.05
µg l <sup>-1</sup>.</p>

<div class="imgcontainer-l" style="width:322px;">
<p class="caption">Structure of Acetochlor<br />
N-(ethoxymethyl)-2-chloro-6'-methylacetanilide</p>
<img src ="struct.gif" alt = "drawing of chemical structure" />
</div>

<hr style="width:0%;" />

<h2>PROCEDURE</h2>

<ol style="list-style-type:upper-roman;">

<li><h3>APPARATUS</h3>

<p>A Hewlett-Packard (HP) Model 5890 Series 2 Gas Liquid Chromatograph equipped 	with an HP 7673A Autosampler and an HP 5972 Mass Selective Detector was used for 	all analyses.  A 95% dimethyl-5% diphenyl polysiloxane column is employed with  	dimensions of 30m x 0.25mm internal diameter x 25µm film thickness.</p>

<p>All other equipment is standard and is readily available from laboratory 	suppliers.</p>

</li>
<li><h3>REAGENTS</h3>

<p>The required solvents should be purchased as high purity grades from the 	suppliers (eg. Curtin Matheson Scientific Inc., Houston, TX).</p>

<p>Acetochlor analytical grade standard is available via the Acetochlor Registration Partnership (ARP) at Richmond, CA.</p>


<table class="table zebra">
<thead><tr>
<td></td>
<th scope="col">Methanol</th><th scope="col">Hexane</th>
<th scope="col">Dichloromethane</th>
</tr></thead>

<tbody>
<tr><th scope="row">Harmful Vapour</th>
<td>Y </td> <td> Y </td><td> Y </td></tr>
<tr><th scope="row">Highly Flammable</th> 
<td> Y </td> <td> Y </td><td> N </td></tr>
<tr><th scope="row">Risk of Irreversible Effects </th>
<td> N </td><td> Y </td> <td> Y</td></tr>
<tr><th scope="row">Recommended Limit (RL)/ppm </th>
<td> 200 </td><td> 100 </td> <td> 100 </td></tr>
</tbody>
</table>

<h4>STANDARD SOLUTIONS</h4>

<p>Weigh out accurately using a five figure balance, sufficient analytical standard to  allow dilution in methanol to give a 1000 µg ml <sup>-1</sup> stock solution in a  volumetric flask.  Make serial dilutions of this standard to give 100 
µg ml <sup>-1</sup>, 10 µg ml <sup>-1</sup>, 1.0 µg ml <sup>-1</sup>  and 0.1 µg ml <sup>-1</sup> in methanol.  These standards are used to fortify  samples.</p>

<p>Standard solutions in hexane should also be prepared to produce a 0.005 
µg ml <sup>-1</sup> standard to routinely use as a bracketing standard when quantifying samples.  These should be diluted from the 100 µg ml <sup>-1</sup>  standard solution in methanol, to give a 10 µg ml <sup>-1</sup>, 1.0 µg ml <sup>-1</sup>, 0.1 µg ml <sup>-1</sup>, 0.01 µg ml <sup>-1</sup> and 0.005  µg ml <sup>-1</sup> standards in hexane. </p>

<p>When not in use, always store the standards solutions in a refrigerator at < 7°C to prevent decomposition and/or concentration of solvent strength.  Analytical  standards are assumed to be stable for 4 months from the date of the preparation of the  initial stock solution.  After this period, a new set of standard solutions must be  prepared. </p>

<h4>SOLID PHASE EXTRACTION (SPE) COLUMN CALIBRATION</h4>

	<ol style="list-style-type:lower-alpha;">

	<li><p>Prepare the solid phase clean-up apparatus by inserting the relevant number  	of Isolute<sup>TM</sup> C18 endcapped columns (1 g, 6 cc) into the adaptors on top  	of a vacuum manifold.  Connect the manifold to a vacuum line.</p></li>

	<li><p>Condition each column using the following procedure.  Pipette methanol (5  	ml) onto the top of each column and apply the vacuum. Draw the solvent through the  	column at a rate of ˜5 ml min<sup>-1 </sup> down to the column frit to 	prevent the column going dry.  Repeat the procedure using ultra-pure water (5 ml).	</p></li>

	<li><p>Fortify ultrapure water (250 ml) with 0.25 µg of acetochlor 	(equivalent to a 1.0 µg l<sup>-1 </sup> recovery) in duplicate.  </p></li>

	<li><p>Fix a column adaptor into the top of each column and insert a reservoir  	(60ml).  Load the sample into the reservoir and draw the water through the column  	under a medium vacuum (flow rate of ˜ 20 ml min<sup>-1</sup>). Once all the  	water has been loaded, maintain maximum vacuum for approximately 10 minutes to dry  	the columns.</p></li>

	<li><p>Close the vacuum and if any globules of water are retained on the walls of  	the C18 column absorb them onto absorbant laboratory paper roll.  Remove the  	adaptors and reservoirs and place suitable labelled collection vessels in the rack  	within the vacuum manifold. </p></li>

	<li><p>Pipette hexane/dichloromethane (60:40 v/v) (6 ml) onto the top of each  	column.  Reapply a low vacuum and elute the analyte into the collection tubes at a  	rate of ˜5ml min<sup>-1</sup>, again only drawing the solvent through to the  	level of the column frit. </p></li>

	<li><p>Dilute each sample to an accurate volume (eg. 5 ml) using 	hexane/dichloromethane and transfer an aliquot (˜1.5 ml) to an appropriate  	autosampler vial and analyse using the conditions described in section 3.4.</p>	</li>
      
	<li><p>If all the acetochlor has been recovered, the columns are calibrated and the  	method is ready for use.  However if all the acetochlor is not accounted for,  	repeat the above procedure increasing the composition of dichloromethane in the  	elution solvent in steps of 20% until all the acetochlor is accounted for.</p></li>

	</ol>

</li>
<li><h3>SAMPLE COLLECTION</h3>

<p>Groundwater, lysimeter water or river water samples are collected from source using  sampling techniques consistent with those employed for low level residue analysis.   Ideally samples should be collected directly into a suitable container eg. glass bottle  or high density polyethylene (HDPE) bottles (500 ml volume or greater).  If no control  water sample is available, collect enough sample (>500 ml) to allow fortification of  the water sample as an external recovery. </p>

</li>
<li><h3>SAMPLE WORK-UP</h3>

	<ol style="list-style-type:lower-alpha;">

	<li><p>Accurately measure out 250 ml (+/- 2 ml) of water sample into a 250 ml  	measuring cylinder.  Transfer the water to a suitable container eg. storage jar.   	NB.  If 250 ml of water is not available, take the maximum volume possible through  	the analytical procedure.  In this case the LOD for acetochlor will need to be  	reevaluated.</p></li>

	<li><p>Fortify at least two control samples by the addition of an appropriate  	amount (1 ml or less) of the 0.1 or 1.0 µg ml<sup>-1</sup> acetochlor  	standard in methanol, using either a syringe or pipette.</p></li>

	<li><p>An untreated control sample must be analysed routinely with each set of  	samples.  Reagent blanks should be taken through the complete analytical procedure  	as required.</p></li>

	</ol>

</li>
<li><h3>COLUMN CLEAN-UP</h3>

<p>Prior to this clean-up procedure being utilised for the first time, the columns should  be calibrated using the procedures described in Section 2.</p>

	<ol style="list-style-type:lower-alpha;">

	<li><p>Prepare the solid phase clean-up apparatus by inserting the relevant number  	of Isolute<sup>TM</sup> C18 endcapped columns (1g, 6 cc) into the adaptors on top  	of a vacuum manifold.  Connect the manifold to a vacuum line. </p></li>

	<li><p>Condition each column using the following procedure.  Pipette methanol (5  	ml) onto the top of each column and apply the vacuum. Draw the solvent through the  	column at a rate of ˜5 ml min<sup>-1</sup> down to the column frit to prevent  	the column going dry.  Repeat the procedure using ultra-pure water (5 ml).</p></li>

	<li><p>Fix a column adaptor into the top of each column and insert a reservoir  	(60ml).  Load the sample into the reservoir and draw the water through the column  	under a medium vacuum (flow rate of ˜ 20 ml min<sup>-1</sup>).  Once all the  	water has been loaded, switch to maximum vacuum for approximately 10 minutes to dry  	the columns.</p>

      <p>Alternatively, the water may be transferred onto the column under vacuum through  	plastic tubing.  Pipette ultra-pure water (4 ml) onto the top of each column.   	Insert a length of plastic tubing of the correct diameter through the hole in the  	column adaptor to obtain a seal.  Place the other end of the tube into the water  	container and apply the vacuum, thus drawing the water through the column.</p></li>

	<li><p>Close the vacuum and if any globules of water are retained on the walls of  	the C18 column absorb them onto absorbant laboratory paper roll.  Remove the  	adaptors and reservoirs and place suitable labelled collection vessels in the rack  	within the vacuum manifold. </p></li>

	<li><p>Pipette hexane/dichloromethane (60:40 v/v) (6 ml) onto the top of each  	column.  Reapply the vacuum and elute the analyte into the collection tubes at a  	rate of ˜5ml min<sup>-1</sup>, again only drawing the solvent through to the  	level of the column frit. </p>

      <p>In certain circumstances, a small volume of water may have been retained on the  	column and will be eluted into the collection tubes.  This will be clearly visible  	as the lower immiscible layer.  Remove the aqueous layer using a Pasteur pipette  	and continue with the method. </p></li>

	<li><p>Dilute all samples to an accurate volume (eg. 5 ml) using 	hexane/dichloromethane and transfer an aliquot (˜1.5 ml) to an appropriate  	autosampler vial in preparation for analysis.  NB.  If a volume of water <250ml  	was available to extract, the final sample volume may be decreased in order to  	lower the LOD.  In this case the sample will be evaporated to a known volume (eg. 1  	ml) under a steady flow of air.</p></li>

	</ol>

</li>
<li><h3>RESIDUE DETERMINATION</h3>

<p>Analysis should be carried out using a Gas Liquid Chromatograph (GLC) fitted with a  mass selective detector (MSD).  A standard solution must be injected after a maximium of  four sample injections.  If particularly dirty traces are obtained with certain water  types, a washing solvent (eg. acetone) should be injected at intervals throughout the  analytical run.</p>

<p>The conditions for the analysis by GLC will depend upon the equipment available.  The  operating manuals for the instruments should always be consulted to ensure safe optimum  use.  The low level work described in this text should ideally be carried out on a "clean system" to ensure optimum results.  This will require a new column,  septum, liner and clean injection port prior to the initial work commencing.  Running  this method alongside other environmental analyses may result in poor chromatography and  loss of sensitivity.  The following conditions have been found to be satisfactory in our  laboratories using the instruments detailed below. </p>

<table class="table zebra">
<caption>Gas Liquid Chromatograph Conditions</caption>
<tr><th scope="row">Injection technique</th><td> Splitless </td></tr>
<tr><th scope="row">Head Pressure </th><td> 8.3 psi </td></tr>
<tr><th scope="row">Injection Volume</th><td> 1 µl<br />
(NB.  this may be increased to a maximum of 5 µl using
these conditions) </td></tr>
<tr><th scope="row">Liner</th><td> Restek presilanised double gooseneck packed
with a plug of silanised pesticide grade glass wool.</td></tr>
<tr><th scope="row">Injector Temperature</th><td> 250°C </td></tr>
<tr><th scope="row">Detector Temperature</th><td> 275°C </td></tr>
<tr><th scope="row">Temperature Program</th><td> 60°C(1min) to 240°C
@ 20°C min<sup>-1 </sup> to 280°C(2min) @ 40°C min<sup>-1</sup><br />
(NB.  During the analysis of certain matrix types containing more organic
coextractants, it may be necessary to modify the temperature program in order to
obtain acceptable chromatograms eg. lower the initial ramp to
10°C min<sup>-1</sup>) </td></tr>
</table>

<table class="table zebra">
<caption>Mass Selective Detector Conditions</caption>
<tbody style="vertical-align:top;">
<tr><th scope="row">Acquisition Mode</th>
<td colspan="2">Selective Ion Monitoring (SIM) </td></tr>
<tr><th scope="row">Solvent Delay</th>
<td colspan="2"> 9.50min </td></tr>
<tr><th scope="row">Electron Multiplier</th>
<td colspan="2"> 2500 volts </td></tr>
<tr><th scope="row">Electron Energy</th>
<td colspan="2"> 70 eV </td></tr>
<tr><th scope="row">System Calibration</th>
<td colspan="2">Manual tunes carried out weekly using ions 131,219,219. <br />
NB.  This factor is critical in achieving required sensitivity. </td>
</tr>
<tr><th rowspan="5" scope="rowgroup">Compound Groups</th>
<td scope="row">Group 1</td><td>Acetochlor</td></tr>
<tr><td scope="row">Target Ions</td><td> m/z 146, 162 </td></tr>
<tr><td scope="row">Dwell time per ion</td><td>: 150 msec </td></tr>
<tr><td scope="row">Resolution</td><td>: Low </td></tr>
<tr><td scope="row">Group Start Time</td><td>: 9.50 min </td></tr>
</tbody>
</table>

</li>
<li><h3>CALCULATIONS</h3>

<p>Residues of acetochlor may be calculated in µg l<sup>-1</sup> for each sample  extract using a mean response signal from the standard injections bracketing that sample  as follows:</p>

<p>Residue  = [ Res(SA) / Res(STD)] [ Conc(STD) / Conc(SA) ] [Inj(STD) / Inj(SA) ]</p>


<p>Res(SA) = Peak height / area for sample </p>
<p>Res(STD) = Average peak height / area for bracketing calibration standards </p>
<p>Conc(STD) = Concentration of compound in standard (µg l<sup>-1</sup>) </p>
<p>Conc(SA) = Concentration factor of water in final sample (ie. 250ml to 5ml = 50) </p>
<p>Inj(STD) = Standard injection volume (µl)</p>
<p>Inj(SA) = Sample injection volume (µl) </p>

<p>These sample residues should be further corrected using the average percentage recovery. i.e. calculate each recovery as above and express as a percentage of the  fortification level.  Then average all the recovery percentages for use in the  calculation below.  NB.  Do not correct sample residues down where the average percentage  recovery is greater than 100%. </p>

<p>Corrected Residue = ( Residue / APR ) ( 100 µg/l )</p>


<p>APR = Average Percentage Recovery</p>

</li>
<li><h3>RECOVERY EXPERIMENTS</h3>

<p>In ARP laboratories to date, the method described above has been applied to the analysis of lysimeter water and well water, but should be applicable to all water types.   A range of untreated samples of each were accurately fortified with 0.05 - 2.00 µg  l<sup>-1</sup> acetochlor before extraction.</p>

<p>Recoveries ranged from 71 - 104% with a mean recovery of 91% and a relative standard  deviation of  10.8.</p>
      
</li>
<li><h3>APPARATUS</h3>

	<ol style="list-style-type:lower-alpha;">

	<li><p>Measuring cylinders (250 ml) available from VWR Scientific, PO Box 7900, San  	Francisco, CA 94120 (Tel: 415-467-6202). </p></li>

	<li><p>Polypropylene wide neck storage bottles (250 ml), available from VWR  	Scientific, PO Box 7900, San Francisco, CA 94120 (Tel: 415-467-6202). </p></li>

	<li><p>Solid Phase Extraction Columns (1 g, 6 cc C18 endcapped), available from  	Varian Sample Preparation Products, 24201 Frampton Avenue, Harbor City, CA 90710 
      (Tel: 310-539-6490).</p></li>

	<li><p>Vacuum Manifold, available from Varian Sample Preparation Products, 24201  	Frampton Avenue, Harbor City, CA 90710 (Tel: 310-539-6490).</p></li>

	<li><p>Graduated centrifuge tubes (Precalibrated) available from VWR Scientific, PO  	Box 7900, San Francisco, CA 94120 (Tel: 415-467-6202). </p></li>

	<li><p>Gas chromatograph with a Mass Selective Detector, eg. HP5890 and autosampler  	HP7673A plus detector (HP5972 MSD) and standalone PC integrator.  Available from  	Hewlett Packard Co., PO Box 1000, Avondale, PA 19311-1000 (Tel: 800-223-9700).</p>	</li>

	<li><p>Analytical gas chromatography capillary columns : 30m x 0.25mm id with a  	0.25µm df: HP 5 from Hewlett Packard Co., PO Box 1000, Avondale, PA 19311- 	1000 (Tel: 800-223-9700).</p></li>

	<li><p>Crimp cap autosampler vials, microvials and caps, available from Hewlett  	Packard Co., PO Box 1000, Avondale, PA 19311-1000 (Tel: 800-223-9700).</p></li>

	</ol>

</li>
</ol>

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