ESTABLISHMENT OF REENTRY INTERVALS FOR

ORGANOPHOSPHATEoTREATED COTTON
FIELDS BASED ON HUMAN DATA
II. AZODRIN, ETHYL AND METHYL PARATHION
G. W. WARE, D. P. MORGAN, M. D.,
BETTY J. ESTESEN, and W. P. CAHILL
Department of Entomology
University of Arizona
Tucson, Arizona 85721

Four human volunteers entered Azodrin, methyl- or ethyl-parathion-treated

cotton fields for 5-hour working periods 24-hours after treatment. Foliage residue
levels, and skin, clothing, inhalation, and biomedical data were obtained. Foliage
residues indicated Azodrin > ethyl > methyl parathion, with degrees of clothing
and hand contamination, personal absorption and effect of blood ChE correspond-
ing with relative foliage residue levels of the three insecticides. There was no effect
on ChE from exposure to methyl parathion; however, Azodrin produced a drop in
RBC ChE, while ethyl parathion resulted in a slight lowering of both RBC and
plasma ChE. Dermal penetration was the principal route of pesticide absorption in
this work situation.

Introduction
In an earlier study (Ware et al. 1973) it was shown that serum parathion, serum and
red blood cell cholinesterase (ChE) activities, and urinary excretion o f para-nitrophenol
(PNP) in exposed individuals were far more useful for evaluating possible potential
parathion poisoning hazard than skin and clothing contamination data. These studies,
however, were based on 30-minute human exposures at 0, 12, 24, 48 and 72 hours after
the insecticide application and require extrapolation to estimate the effects on humans
exposed for extended periods up to one working day.

Because of the increased use o f parathions and other organophosphate insecticides on

cotton as substitutes for DDT, the expansion o f cotton pest management programs
involving large numbers of cotton scouts, and the dearth of human exposure information
for establishing reentry intervals, there is a great need for such information.

The purpose of this work was to test empirically the safety of reentering cotton fields
24 hours following application o f three organophosphate insecticides commonly used in
Arizona cotton culture. During a 5-hour period, 4 volunteers carried on the duties

This work is a contribution to Regional Project W45, "Residues of Selected Pesticides - Their
Nature, Distribution, and Persistence in Plants, Animals, and the Physical En~onment." University of
Arizona Agricultural Experiment Station journal series #2120.

Archives of Environmental Contamination 117

and Toxicology, Vol. 2, No. 2, 1974, © 1974
by Springer--Verlag New York Inc.
118 G.W. Ware et al.

involved in inspection of cotton plants, while the following variables relevant to assess-
ment of pesticide exposure hazard were measured:

1. Foliar residue levels of applied pesticide during field exposure.

2. Pesticide contamination of hands and lower arms.
3. Adsorption of pesticide onto clothing.
4. Ambient air concentrations of pesticide.
5. Pesticide present in the blood.
6. Urinary excretion of the metabolite, PNP.
7. Effect of the field exposures on plasma and red cell ChE activities of blood of
exposed subjects.

Experimental
During the three reentry experiments a total of six volunteers were involved; four
participated in each reentry. Each wore blue jeans and a T-shirt from the same manufac-
turer purchased specifically for these field studies. Head coverings were optional.

Carrying an insect sweep net, each volunteer remained in the field, treated 24 hours
earlier, for a total exposure of 300 minutes, simulating the activities and approximate
maximum exposure of a cotton entomologist or checker. Portable air samplers were worn
by two of the four volunteers.

In all three reentry experiments, the biomedical, field and laboratory protocol
followed that shown in Table I, involving one day pre- and two days' post-exposure. This
protocol required exactly 5 hours of movement through treated foliage. Precise times of
each activity were somewhat variable depending on the time used in activities out of the
field. Thus, as much as 6.5 to 7 hours passed while acquiring 5 hours of field exposure.

Methyl parathion. The first of three insecticide reentry studies involved methyl
parathion (phosphoric acid, O, O-dimethyl O-p-nitropenyl ester) applied to short staple
(upland) cotton at the recommended rate of 1.0 lb a.i./acre. The insecticide was applied
as an emulsion in nine gallons of spray per acre, with an International 12-row, high-
clearance (Hi-Boyj self-propelled ground sprayer, using three #6 cone nozzles per row and
40 p.s.i., beginning at 7:00 A.M. on July 20, 1972. The cotton was planted in 40-inch
rows, averaged 5.5 ft in height, varying from three to six ft, and had abundant squares,
blooms, and bolls, with foliage from adjoining rows intertwined. This resulted in
maximum contact of inspection personnel with foliage surfaces, to the extent that
clothing was stained green in several areas at the end of the field study.

The spray was applied to four one-acre blocks, 12 rows wide by 1000 ft tong within
the same field near Coolidge, Arizona. These plots had been treated three times pre-
viously at approximately five-day intervals with methyl parathion at 1.0 lb a.i./acre,
beginning July 5.

The temperature at time of application rose from 85 ° to 90°F, reaching a maximum

of 100 ° and a minimum of 74°F for the 24-hour residue aging period.
 Reentry Intervals for Organophosphate-Treated Cotton Fields 119

Table I. Protocol for 1972 Reentries into Cotton Fields Treated with
Azodrin, Methyl, or Ethyl Parathion

Day prior to field reentry

7:00-10:00 A.M. Field treated with insecticide
24-hr control urine collected
Blood sampled for ChE and insecticide
Day of field reentry
Before reentry Dressed in field clothing, air samplers
activated, bladder emptied
7:00 A.M. First sampling of leaves for insecticide
7:00-10:00 A.M. Cotton inspected
10:00 A.M. Second sampling of leaves for insecticide
Blood sampled for ChE and insecticide
Air sampler glycol exchanged
10:30-11:30 A.M. Cotton inspected
1 1 : 3 0 A.M. Hands and wrists washed with solvent
11:30-12:30 P.M. Lunch
12:30-2:30 P.M. Cotton inspected
2:30 P.M. Third sampling of leaves for insecticide
Blood sampled for ChE and insecticide
Hands and wrists washed with solvent
Air sampler glycols stored
Clothing removed and bagged
Day following field reentry
8:00 A.M. 1st 24-hr urine completed
Blood sampled for ChE and insecticide
Second day following field reentry
8:00 A.M. 2nd 24-hr urine completed

Azodrin, The second study involved Azodrin (phosphoric acid, dimethyl ester, ester
with cis-3-hydroxy-N-methyl crotonamide) applied on July 27 at the rate of 1.28 lb
a.i./acre to a 4.8-acre block in the same field as the first with the same ground equipment
and application parameters as the first.

The temperature at time of application was 90-92 ° with a maximum of 108 ° and a
minimum of 78 ° for the 24-hour residue aging period.

Ethyl parathion. The third study involved ethyl parathion (phosphoric acid, O,
O-diethyl O-p-nitrophenyl ester) applied on August 3 at the rate o f 1.0 lb a.i./acre to
a seven-acre block in the same field with the same ground equipment and application
parameters as the two previous experiments.

The temperature at time of application was 88-89°F, with a maximum of 101 ° and a
minimum of 74°F for the 24-hour residue aging period.
120 G.W. Ware et al.

Residue sampling. Leaf samples were collected by each of the four volunteers at the
beginning, midway, and termination times of each study. Each sample consisted of t 00
leaves picked singly from the top, middle and bottom of randomly selected rows, but not
within 50 ft of the row ends, to avoid irregular spray patterns. One control sample was
collected at each of the three sampling periods. The whole leaves were placed in
individually marked plastic bags immediately after picking and chilled in an ice chest for
return to the laboratory.

Each volunteer's hands were rinsed at the lunch break and again at the termination of
the experiment. For the parathions, 125 ml of hexane were used, while distilled water
was used for Azodrin. The rinses were collected by funnel in 200-ml screw cap sample
bottles which were held in the ice chest for return to the laboratory. T-shirts and blue
jeans were placed in individual plastic bags, which were identified and held in ice chests
for return to the laboratory.

Air samples were collected with portable Mine Safety Appliance "Monitaire Samplers"
(2.83 liters/rain) which were attached to the waists of two subjects with the end of the
air intake tubes pinned to the upper front parts of the subjects' T-shirts. After 2.5 hours
of sampling, glycol impingers were exchanged for fresh ones. Samplers were then carried
by the alternate subjects during the remaining hours of field exposure.

Sample extraction. For determining dislodgeable residues, the leaves were center-
punched in the laboratory 10 at a time, using a sharpened 36-ram aluminum tube. Each
100-disc sample was washed twice for two minutes in a 600-ml beaker using 225 ml of
benzene for either of the parathions, or water in the case of Azodrin. The extracts were
combined and refrigerated in labeled bottles. Aliquots of the parathion extracts were
diluted, as appropriate, for gas chromatography.

Aqueous Azodrin leaf washes were partitioned into chloroform by adding 14 g of

NaC1 to 50 mt and extracting three times with 50 ml of chloroform each time. The
chloroform extracts were combined, dried through anhydrous sodium sulfate, and held
in the freezer.

Blue jeans were extracted for the parathions by one soaking in 6 liters of hexane for
30 minutes. T-shirts were extracted three times in a total of 2.5 liters of hexane, for a
period of about 15 minutes. Aliquots of these were held in sample jars with Na2 SO4 added
for removal of water, and held in the freezer. For Azodrin extraction, the blue jeans and
T-shirts were washed with distilled water in volumes described above. Aliquots were held
in the refrigerator to be partitioned into chloroform as previously described.

Hexane hand rinses for the parathions were held in sample jars with Na2SO 4 added for
water removal and held in the freezer. Aqueous hand rinses for Azodrin were refrigerated
and later partitioned into chloroform.

Chloroform extracts of Azodrin were concentrated with an air stream to about 0.1 ml
and returned to volume with 10% acetone in hexane for gas chromatography.
 Reentry Intervals for Organophosphate-Treated Cotton Fields 121

Air samples were extracted for parathions by diluting the ethylene glycol with distilled
water and partitioning into benzene, which was then dried over anhydrous Na2SO4 and
concentrated for gas chromatographic analysis. Azodrin air samples were diluted with
water, salt added, partitioned into chloroform, and processed for gas chromatography as
described above.

Gas chromatographic analyses. All determinations of Azodrin and methyl and ethyl
parathion and their oxons were made by gas chromatography, using a flame-photometric
detector sensitive to phosphorus-containing compounds. For the parathions and their
oxonsthe chromatograph was equipped with a 6 ft × 4 mm ID Pyrex glass column packed
with 100/120 mesh Chromosorb W HP containing 5% by weight of SE-30. For methyl
parathion the operating parameters were: 90 ml/min, 231, 204, and 205°C; methyl
paraoxon 60 ml/min, 225, I95, and 225°C; ethyl parathion, 73 ml/min, 225, 198, and
240°C; and ethyl paraoxon 73 ml/min, 225, 186, and 235°C., respectively, for nitrogen
gas flow, inlet, column and detector temperatures.

For Azodrin the chromatograph was equipped with a 2.75 ft × 4 mm ID Pyrex glass
column packed with a 1 : 1 mixture of 80/100 mesh Gas Chrom Q containing 2% Reoplex
400, and 60/80 mesh Chromosorb W (Fe free and acid washed) containing 5%QF1.
Operating parameters were 68 ml/min, 230, 196, and 239°C., respectively, for nitrogen
flow and inlet, column, and detector temperatures.

Quantitation was by peak height and compared with a standard curve made from
standard solutions containing 0.2 ng//at hexane for the parathions, 0.5 ng//al hexane for
their oxons, and 1 ng//al of 15% acetone in hexane for Azodrin.

Analytical recoveries were: methyl parathion, 90%; methyl paraoxon 120%; ethyl
parathion, 105%; ethyl paraoxon, 100%; and Azodrin, 91%, depending on the substrate.
None of the analytical data were adjusted for recoveries.

Serum concentrations of insecticide. Sera collected before, during and after field
exposures to parathions were analyzed for methyl or ethyl parathion using hexane
extraction, GLC separation, then quantitation by electron capture and phosphorus
detectors (Roan et al. 1969).

No attempt was made to detect Azodrin in serum, as this water-soluble pesticide

cannot be satisfactorily extracted and measured by presently available methods.

Cholinesterase activities. Measurements were made by the method of Michel (1949),

and were converted to international units by an empirical equation. Normal ranges
(based on tests on 107 controls) by this method are 2.4 to 5.5 #M/ml/min for plasma and
9.0 to 15.1/aM/rrd/min for RBC.

For each of the three reentry studies, the four sequential blood samples from each of
four subjects were collected, then analyzed together in the same batch, using identical
122 G.W. Ware et al.

substrate and buffer solutions. This precaution minimized measurement error as a source
of variation between serially collected specimens.

Urine analysis for pamnitrophenol. Subjects emptied their bladders an hour or more
before entering the treated fields. One 24-hour urine sample was collected up to ap-
proximately the same time of the morning following field entry. A second specimen was
collected in the same manner, including 24 to 48 hours after field entry. Both specimens
were analyzed for PNP by the method of Cranmer (1970). PNP excretion was calculated
as the product of volume times analytical PNP concentration.

Results

Leaf residues. The dislodgeable leaf surface residues of Azodrin, methyl and ethyl
parathion, and the paraoxons at the time of each reentry study are presented in Figure 1.
Each point on the 6-hour degradation curve represents the mean of four 100-leaf samples,
expressed as milligrams of parent compound and micrograms of paraoxons per square
meter of leaf surface. The Azodrin residue appears to approximate that of ethyl parathion
at 24-hours when viewed from its application rate of 1.28 lb vs 1.0 lb/acre for parathion.
Methyl parathion disappears quite rapidly, as indicated by the initial residue at 24 hrs,
and its apparent continued decline during the reentry period. Residues of Azodrin,
methyl and ethyl parathion, and the paraoxons on cotton reported in an earlier study
(Ware e t aL 1972) on a ppm basis show similar degradation responses: methyl parathion
disappears more rapidly than ethyl parathion followed by Azodrin and ethyl paraoxon
appears at greater levels and disappears slower than methyl paraoxon.

6
/ O
J
J
5 Azodrin . /
Ethyl Parathion

~ 3
dE --Thions
2
• ~ ~ -- Methyl Parathion

n 0 . . . . . . .

021 × _E
t h .ylParaoxon
. . . ~x [[ 2 0 0 .

01 --Oxons 100
Methyl Paraoxon
e ~ -- --e I
0 0
24 2'6 28 ' 30
Hours after application

Fig. l. Foliar residues of insecticide during the hours of field exposure.

 Reentry Intervals for Organophosphate-Treated Cotton Fields 123

Biomedical surveillance. None of the subjects participating in this study experienced

symptoms suggesting adverse effects of chemical exposure. Physical activity in these high
environmental temperatures induced sweating and dehydration, which was compensated
for by liberal ingestion of fluids. No one manifested symptoms or showed signs such as
miosis, muscle trembling, nausea, headache, or dizziness suggestive of poisoning by
cholinesterase-inhibiting substances.

Measures of pesticide absorption and the effects of pesticide absorption corresponded

qualitatively with the relative magnitudes of foliar residue and with measured quantities
of pesticide adsorbed by clothing and hands. Thus, the amounts of methyl parathion
getting into the body were insufficient to produce detectable amounts in the blood
(Table II), or to affect the cholinesterase activities of plasma or cells (Figures 2 and 3).
The latter result is not surprising in the light of the finding of Rider et at. (1971) that
an adult man must ingest 30 mg of methyl parathion daily to experience a consistent
depression of cholinesterase activity.

By contrast, ethyl parathion, present on foliage in three to four times the concentra-
tion of the methyl compound, was absorbed in quantities that were readily and consis-
tently detectable in blood. There was a weak, equivoval effect on plasma and RBC
cholinesterase activities. The apparently greater effectiveness of the ethyl form of parathion
in these studies was clearly dependent on two factors: (1) the higher leaf residue to which
personnel were exposed, and (2) the lower threshold effective dose of the ethyl form of
parathion, about 3.5 rag/day (Williams et aL 1958).

Table II. Serum Parathion Concentrations and 48-hr PNP Excretions

During and After 5-hr Field Exposures to Cotton Treated 24 hrs Previously
with Methyl or Ethyl Parathion (1 lb/acre)

Serum parathion (ppb) 48-hr PNP

Subject 2 hrs 5 hrs excretion (mg)

Methyl parathion
G.W. 0 0 0.15
W.C. 0 0 1.20
D.D.M. 0 0 0.44
D.P.M. 0 0 0.19

Ethyl parathion
G.W. 23 53 0.74
W.C. 13 42 _a
D.D.M. 48 47 1.01
W.W. 55 55 0.93

aSample not collected.

124 G . W . Ware et al.

5-

3
-O

Methyl parathion exposure

0 ! ! I I I I I I ! I I ! I
E 8AM 12N 4PM 8PM 12MT 4AM 8AM

:~ 5
>
"~ 4
to

3-
E

e-

Ethyl parathion exposure

n

0 | I I I ! I I 1 I I I ! I
8AM 12N 4PM 8PM 12MT 4AM 8AM

3-

il zor'nxsur
i I i ! i i i I ! ! I f ..... 1

8AM 12N 4PM 8PM 12MT 4AM 8AM

Time

Fig. 2. Plasma cholinesterase responses to 5-hour field exposures to residues of three

pesticides. Each plotted line represents one subject.
 Reentry Intervals for Organophosphate-Treated Cotton Fields 125

1615t17~ ~ / ~ ~ .Methyl
parathionexposure.
-o

a.

13

..... ~'
8AM 12N 4PM 8PM 12MT I I
4AM 8AM
I

Ethylparathionexposure
t5-

14-
e~

~ 13-
0
:~ 12 I I i I ! ! I i i I I ""---~
8AM 12N 4PM 8PM 12MT 4AM 8AM
18
~
Azodrinexposure
~ 17

15

14-

13-

12-

11-

10-

I ! I ~ i I ! I I ! ~ ! !
8AM 12N 4PM 8PM 12MT 4AM 8AM
Time
Fig. 3. RBC cholinesterase responses to 5-hour field exposures to residues of three
pesticides. Each plotted line represents one subject.
126 G.W. Ware et al.

Total urinary excretions of PNP (Table II), corresponded in rough qualitative fashion
with the blood pesticide and blood cholinesterase measurements: average excretion in
the methyl parathion study was 0.5 mg, while that in the ethyl parathion reentry was
0.9 mg. As indices of chemical uptake, however, these values must be viewed critically.
Apart from the physiologic probability that PNP is excreted by hepatic as well as renal
pathways (Gardocki and Hazleton 1951), the method of urinary PNP analysis used in our
laboratory did not yield consistent recoveries in the low range of concentrations encoun-
tered in these studies. Refinements in this measurement, and greater knowledge of PNP
excretion by man, are required before quantitative interpretations can be attached to this
parameter of chemical exposure.

The biochemical effect of Azodrin exposure was manifest in a consistent depression of

RBC cholinesterase during and after field exposure (Figure 3). This reflected extraordinary
adsorption of Azodrin to hands and clothing (Table III), a factor of nmch greater apparent
influence than the actual level of foliar residue to which the subjects were exposed
(Figure 1).

Table lIl. Insecticide Residues Extracted from Clothing and Hand Surfaces
Following 5-hr Field Exposure of Four Subjects

Total insecticide (rag)

Methyl Methyl Ethyl Ethyl
Extract parathion paraoxon parathion paraoxon Azodrin
from (mg) (/ag) (mg) (//g) (mg)

Hands

11:30 A.M. 0.2 0.5 0.3 9.0 2.9

2:30 P.M. 0.1 0.4 0.2 7.0 2.8

Shirts 0.2 4.0 6.1 141.0 16.5

Pants 1.7 39.0 9.8 370.0 70.8

It should be pointed out that in none of these reentry studies did blood cholinesterase
measurements actually drop into the "abnormal" range. The value of pre-exposure
measurements in detecting physiologic effects of exposure to cholinesterase inhibitors is
thus reaffirmed.

Total estimated respiratory exposure to pesticide is presented in Table IV. While

detectable amounts of chemical were present in the air in all of the reentry studies, the
quantities were obviously small, and corresponded qualitatively with foliage residue
levels. While pesticide absorption by the respiratory route is assured more hazardous than
dermal absorption (Hartwell and Hayes t965), it seems unlikely that the microgram
 Reentry Intervals for Organophosphate-Treated Cotton Fields 127

doses absorbed over 5 hours in these reentry studies would have significant, or even
measurable, physiologic effects by themselves.

Criteria by which to establish "reasonable safety" of a given reentry interval have not
been officially prescribed. Such criteria might be based on (1) symptomatology, (2) bio-
chemical effects, such as blood cholinesterase depression, (3) rates of urinary metabolite
excretion, or (4) measurement of native pesticide in the blood of exposed workers. One
criterion that appears relatively simple and rational is that of "no effect" on the choline-
sterase activities of plasma and erythrocytes. This might well be defined as an absence of
statistically significant (P < 1%) depressions of ChE levels as a result of exposure, based
on an arbitrary minimum number of subjects.

Although our own study made use of too few subjects to examine statistically, it is
certainly possible to make some judgments of the propriety of a 24-hour reentry interval
for the three chemicals studied at the dosages used: (1) There is a strong likelihood that
this interval is safe in the case of methyl parathion, (2) some doubt would attach to the
safety of a 24-hour reentry interval after ethyl parathion application, and (3) a 24-hour
interval after Azodrin application (1.28 lbs a.i./acre) is inadequate.

The cholinesterase curves in Figures 2 and 3 reveal the complexity of the time-course of
cholinesterase activities following exposure to inhibitors. Of the several possible times at
which to make measurements for comparison with pre-exposure values, the "immediate
post-exposure" set appeared most likely to reveal a depression. The "following morning"
values show a persisting effect, and probably should be part of a standard reentry pro-
tocol to ensure that effects of slowly absorbed or slowly metabolized pesticides will be
detected. The "during exposure" measurements were the least important of the three sets
we collected.

Table IV. Estimated Respiratory Dosages of Volunteers Working 5 hrs

in Cotton Fields Treated 24 hrs Previously
with A zodtin, Methyl, or Ethyl Parathion

Previously Mean air Estimated

applied concentration of respiratory
pesticide pesticide, ng/L a #g/5 hoursb

Methyl parathion 0.2 1.2

Ethyl parathion 3.2 19.2

Azodrin 4.5 27.0

aCalculated from glycol content of pesticide divided by 850 liter air volume passed
per 5 hours.
bCalculated assuming average pulmonary ventilation of 20 liters per minute, and
100% absorption efficiency.
128 G.W. Ware et al.

Conclusions
1. Foliage residues were distinctly lowest in the case of methyl parathion. Only methyl
parathion showed decay during the day of field test. Degrees of contamination, personal
absorption, and effect on blood enzymes correspond qualitatively with relative levels of
foliage residues of the three pesticides.

2. All reentry studies were completed without symptomatic or objective indications of

organophosphate poisoning of any subject.

3. Cholinesterase tests showed no effect of exposure to methyl parathion residues.

There was an equivocal effect of ethyl parathion exposure on blood chotinesterases.
Azodrin exposure produced a consistent drop in RBC cholinesterase, without any apparent
effect on plasma ChE. RBC effect showed some recovery by the following morning. Even
the Azodrin exposure did not reduce blood cholinesterase to values below "normal."

4. Urinary excretion of PNP did not reflect sufficient dosage of either methyl or
ethyl parathions to indicate a probability of poisoning, or even a likely effect on blood
cholinesterases (Rider et al. 1971 and Williams et al. 1958). Recovery efficiency of
analysis used was not consistently satisfactory, and urinary PNP excretion may therefore
have been substantially underestimated. According to Rider et aL (1971), a dosage of at
least 28 mg per day of methyl parathion is needed to affect blood cholinesterase activity.
Williams et al. (1958) estimated 3.5 mg per day as the minimum effective dose of ethyl
parathion. No analogous datum is available for Azodrin.

References
Cranmer, M. Determination of p-Nitrophenol in human urine. Bull. Environ. Contain.
Toxicol. 5,329 (1970).
Gardocki, J. F., and L. W. Hazleton. Urinary excretion of the metabolic products of
parathion following its intravenous injection. J. Amer. Pharmaceutical Assoc. 40,
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Hartwell, W. V., and G. R. Hayes, Jr. Respiratory exposure to organic phosphorus insec-
ticides. Arch. Environ. Health 11,564 (1965).
Michel, H. O. An electrometric method for the determination of red blood cell and
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Rider, J. A., J. I. Swader, and E. J. Puletti. Anticholinesterase toxicity studies with
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Manuscript received June 2, 1973; accepted September 21, 1973.