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These data, and the species examined for chlordane susceptibility by
Trudgill et_ al. (1971) as listed in Table 55 argue that heptachlor and
chlordane are toxic to some but not all microorganisms, so that major
changes in the composition of soil microbial populations must be ex-
pected in the presence of these compounds, even if overall numbers of
microorganisms remain constant.
Plants—Stitt and Evanson (1949) reported that: 34.8 Ibs/A (38.9 kg/ha)
of chlordane adversely affected cucumbers, bush beans, and turnips.
Boswell (1955) noted that phytotoxicity was more likely in poor soils
than rich, presumably because the latter have greater adsorptive capa-
city.  In quartz sand chosen for its lack of adsorptive capacity, chlor-
dane significantly reduced the growth of corn roots, but not: of pea
roots while heptachlor increased root growth of both corn and pea roots,
the latter significantly (Lichtenstein et^ al. 1962).  Shaw and Robinson
(1960) found that 200 Ibs/A of chlordane (224 kg/ha) or 120 Ibs/A of
heptachlor (134.4 kg/ha) were required to inhibit the growth of tomatos
or sudan grass.
These data suggest that, except under conditions of extreme soil pover-
ty and gross contamination, neither heptachlor nor chlordane is likely
to exert direct toxic effects on plants.  Even in the absence of pests,
heptachlor reportedly increased yields of several crops (sugar beets,
winter rye, spring wheat, barley, oats, potatoes) for two years after
a single application.  The crop improvement was synergistic with min-
eral fertilizers (Persin 1961).
Invertebrates—The effects of heptachlor and chlordane on soil fauna
were reviewed by Edwards and Thompson (1973) who concluded that chlor-
dane and heptachlor drastically decrease the numbers of earthworms;
considerably decrease the numbers of Co11embc1a> paurapods and soil
mites.  They may also kill some terrestrial molluscs, but do not much
affect springtails or symphelids.  Heptachlor was reported to decrease
the numbers of Aoari-nae and increase the numbers of Collembola when
                                   330

-------
applied to a beet field at 0.6 kg/ha (Khalidov et^ al_. 1968).
Freshwater invertebrates from areas contaminated by chlordane were more
resistant to the pesticide than those from uncontaminated areas  (Naqvi
and Ferguson 1968).  Chlordane at 0.01 ppm reduced shell growth and
shell movement in oysters (Butler et al. 1960).
Fish—The LC,.,. for various fish to chlordane ranged from 0.01 ppm in
48 hours for rainbow trout to 0.082 ppm for goldfish after 96 hours
(Pimentel 1971).  For heptachlor, the LC _ was 0.25 ppm after 24 hours,
but 0.009 ppm after 96 hours in rainbow trout while goldfish had a 96
hour LC5Q of 0.23 ppm (Pimentel 1971).
In mummichogs (Fundulus heteroelitus) heptachlor toxicity was greater
after 24 hours than after 96 hours, either as a result of bioaccumulation
or because of the toxicity of heptachlor epoxide (Eisler 1970a).  Never-
theless, heptachlor was among the least toxic organochlorines (Table
36).  Khan and co-workers (1973) determined the relative toxicities of
chlordane and heptachlor in fish to be less than those of chlordane and
photoheptachlor, respectively.
Amphibians—Heptachlor, but not chlordane, was toxic to toads (Bufo
boreas) and frogs (Saaphiopus hammondii) at 0.1 to 0.5 Ibs/A (0.11 to
0.56 kg/ha) (Mulla 1962).  The 24 hour LC5Q of heptachlor for Fowler's
toad was 0.85 ppm (Pimentel 1971).
Birds—Tucker and Crabtree (1970) listed the acute oral LD Q of chlor-
dane and heptachlor to mallards as 1,200 mg/kg and more than 2,000 mg/
kg, respectively.  Coturnix quail which were fed 0.05 to 0.1 mg hepta-
chlor per day for 18 to 32 days produced normal numbers of eggs of the
normal weight.  Prehatching mortality among the chicks was also normal,
but deaths among newly-hatched chicks were higher for the first week
after hatching.  Survivors xjere normal with respect to survival, age of
sexual maturity, and fecundity.  Egg residues of heptachlor ranged from
one to 17 ppm (Grolleau and Froux 1973).  When applied to fields at
                                   331

-------
agricultural levels, heptachlor has repeatedly been shown to reduce bird
populations as reviewed by Pimentel (1971).
When chlordane in acetone was injected into hens' eggs, no increase in
mortality occurred at levels up to 500 ppm.  Heptachlor at 400 ppm and
500 ppm killed 20 and 47 percent of the chick embryos, respectively
(Dunachie and Fletcher 1969).  When 0.1 ml of one percent: heptachlor
was injected into the yolk sacs of fertile hens' eggs before, incubation,
the number of eggs which hatched was reduced to 65 percent of control
levels (Mclaughlin et_ al. 1962).
Mammals—Estimates for the acute oral LD,-,-. of chlordane in rats include
283 mg/kg (Jones £t al. 1968) and 335 mg/kg in males, 430 mg/kg in fe-
males (Gaines 1969) and 500 mg/kg (Spynu 1964, Martin 1968).  In mice,
Spynu (1969) calculated the acute oral LD  _ to be 220 + 34 mg/kg.  Hep-
tachlor was calculated to have an acute oral LD   of approximately 100
mg/kg in rats (Martin 1968, Gaines 1969);  female rats were less sensi-
tive, with an LD,.n of 162 mg/kg reported by Gaines.  Jones et al. (1968)
                jU
estimated the oral LD _ of heptachlor in rats to be 40 mg/kg, and the
dermal LD ... to be between 200 and 250 mg/kg, as opposed to a dermal
LD,.,, of more then 1,600 mg/kg for chlordane.  Spynu (1964) reported an
acute oral LD n of 210 + 5 mg/kg for heptachlor in mice.  Heptachlor
             jU
and chlordane were in the minority of pesticides which were more toxic
to male than to female rats (Gaines 1969) .
Chlordane decreased the toxicity of subsequent parathion treatments,
apparently by increasing the levels of serum aliesterases (Williams et
al. 1967).  Chapman and Leibman (1971) pointed out, however, that
whereas both DDT and chlordane stimulated  the metabolism of parathion
to paraoxon and to diethylhydrogen phosphorothionate, only chlordane
protected against parathion toxicity.  They concluded that factors
other than enhanced metabolism must account for the chlordane-parathion
interaction.
                                   332

-------
At levels of two to five mg/kg/day given intraperitoneally for 7 days,
chlordane inhibited the uterogenic activity of estrone and decreased the
uterine content of estrogen in rats and mice, and at 10-50 mg/kg/day,
estrone metabolism was also decreased.  Chlordane also increased the
levels of estradiol 178, testosterone, progesterone, and deoxycorticos-
terone, while heptachlor increased estrone metabolism (Welch et^ al.
1969, 1971).  The number of pregnant mice decreased when females were
treated intraperitoneally with 25 mg/kg chlordane per week (Welch et_
al. 1971) .  Mestitsova (1967) found that heptachlor resulted in decreased
litter size within and between generations, a decrease in the survival
of suckling rats, especially between 24 and 48 hours after birth, and
cataracts in survivors.  No clinical toxicity was observed when hepta-
chlor levels of six mg/kg were fed for 18 months.  In another study,
Green (1970) found a decrease in the number of pups born when rats were
fed heptachlor levels equal to the maximum food allowances although no
increase in the number of abnormal pups was found.  In cell culture of
human Chang-strain liver cells, chlordane inhibited the replication of
both vaccinia and polio virus (Gabliks 1967).
Terracini (1967) observed heptachlor to be weakly carcinogenic in rats,
mice, and dogs.  In contrast, no effect of long-term feeding of hepta-
chlor was found by Cabral and co-workers (1972) and a tumorstatic effect
was claimed for chlordane when urethane was used as the carcinogen
(Yamamoto et al. 1971) .  More recent studies demonstrated that mice fed
25 or 50 ppm chlordane had significantly more carcinomas than control
mice (Carter 1974, Train 1975).  Markaryan (1972) considered several
organochlorines, including heptachlor, to be mutagenic with the levels
of induced mutations lower than with alkylating agents or irradiation,
and consisting mostly of chromatid aberrations.  The World Health Or-
ganization characterized chlordane as carcinogenic in one species and
heptachlor as uncertainly carcinogenic (Vettorazzi 1975).
                                   333

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In summary, these data demonstrate that heptachlor and chlordane exert
considerable influence on enzymic and hormonal levels, even at dosages
which are not overtly toxic.  Although gross congenital abnormalities
do not seem a common consequence, chlordane and heptachlor obviously
affect reproduction at all-stages.  Heptachlor and chlordane are car-
cinogenic, and some evidence for mammalian mutagenicity also exists.
                                  334

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Endosulfan
Endosulfan is the common name for 6,7,8,9,10,10-hexachloro-l,5,5a,6,9,
9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide, a non-system-
ic stomach and contact insecticide introduced by Farbwerke Hoechst AG
in 1956 under the name Thiodan.  For its manufacture, the Diels-Alder
adduct of hexachlorocyclopentadiene and cis-l,4-diacetoxybutene is
hydrolyzed to the diol which is then reacted with thionyl chloride.
Endosulfan is a mixture of two isomers, the alpha isomer having a mel-
ting point of 108  to 110 C, and the beta isomer having a melting point
of 208  to 210 C.  The technical product is a brownish crystalline so-
lid with an odor of sulfur dioxide and a melting point of 70  to 100 C.
It has no measurable vapor pressure at 75 C, has a water solubility
less than one ppm, and is moderately soluble in most organic solvents.
Degradation-
Biological—Bacteria and green algae decomposed endosulfan to endosul-
fan-alcohol (Gorbach and Knauf 1971).  Martens (1972) identified the
major metabolic products of microbial endosulfan degradation as the
sulfate and the endodiol.  In soil with natural microbial populations,
                                14                              14
a maximum of 5.4 percent of the   C-endosulfan was converted to   C0_
in fifteen weeks; 30 to 60 percent was converted to endosulfan sulfate
(Martens 1972).  In water, microbial degradation was favored by neut-
ral, aerobic conditions (Greve and Wit 1971).  Under aerobic conditions
unidentified soil bacteria converted aZ-pfcz-endosulfan as well as beta-
endosulfan to their respective alcohols, but the ether was obtained
only from Jeta-endosulfan (Perscheid et al. 1973) .
         14
In mice,   C-endosulfan was converted to its sulfate prior to tissue
storage while fecal excretion included endosulfan itself, endosulfan
diol, and endosulfan sulfate.  Compounds other than the sulfate were
                                  335

-------
apparently restricted to the liver and kidneys (Deema e_t_ al_. 1966).
In rats and mice, the alpha isomer was more rapidly excreted than  the
beta isomer.  Five metabolites of endosulfan were detected, including
the hydroxyether and the gamma-lactone; nevertheless most endosulfan
was recovered unaltered (Schuphan et al. 1968).  When two ewes were fed
             14
0.3 mg/kg of   C-endosulfan, the radioactivity was almost totally  el-
iminated within 22 days; fifty percent was eliminated in the feces, 41
percent in the urine, and one percent was excreted in the milk.  Milk
residues fell to two ppb by the twenty-second day, and to no more  than
0.03 ppb after 40 days.  Urinary metabolites included 1,4,5,6,7,7-hex-
achloro-2,3-bis-(hydroxymethyl)-bicyclo-2,2,l-heptene-5(endosulfan al-
cohol) and l-alpha-hyd-roxy endosulfan  (Gorbach et al. 1968) .
The data on biological degradation of endosulfan are summarized in
Table 58 and Figure 14.
Chemical and physical—In neutral solution, the alpha and beta isomers
each decomposed to two unidentified but not identical compounds, while
in alkaline solution both isomers formed the diol, which was then  open
to further degradation (Schuphan and Ballschmiter 1972) .
Photolytic—When endosulfan was irradiated by UV light at wavelengths
approximating sunlight, the alpha isomer was dechlorinated  in hexane
solution.  The beta isomer was stable to UV light in hexane, but lost
one chlorine if in dioxan-water solution (Schumacher et^ a^. 1971,  1973).
Archer and co-workers (1972) obtained endosulfandiol as the major  pro-
duct of UV irradiation.  Other photoproducts included the a1pha-hydroxy-
ether, a lactone, an ether, and some minor unidentified products,  but
no endosulfan sulfate.  No degradation occurred in the dark (Archer et
al. 1972).  Under laboratory and greenhouse conditions, endosulfan sul-
fate and endosulfan ether were reported to be the major metabolites
(Beard and Ware 1969).
                                  336

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Transport-
Within soil—Of 6.7 kg/ha soil-applied endosulfan, 90 percent of the
residues were recovered from the top 15 cm of soil, and nine percent
from the 15 to 30 cm layer  (Stewart and Cairns 1974) .  When endosulfan
was applied to a broad spectrum of soils in columns, water percolation
of the soils permitted recovery of 64 percent of the endosulfan from
Lakeland sand, but no more  than seven percent from sandy clays.  Loam
recoveries were intermediate (Bowman et al. 1965).
Between soil and water—Endosulfan was found as a pollutant of the
Main, Rhine, and Regnitz rivers in Germany (Herzel 1972), with levels
of up to 0.70 ppb in the Rhine (Greve and Wit 1971).  Richardson and
Epstein (1971) concluded that flocculation would not significantly de-
crease water levels of endosulfan.  Greve and Wit (1971) found that
endosulfan readily adsorbed to river silt, and that 85 percent could
be removed by filtration.
Into organisms—When potato foliage was sprayed eight times with 0.6
kg/ha of endosulfan, both potato peel and pulp contained 0.01 ppm endo-
sulfan (Stewart and Cairns  1974).  Rate of penetration of endosulfan
and its metabolites into beet and bean plants was of the order:  beta
isomer > sulfate > ether > aZp/za isomer > diol.  Only the diol was not
transferred to the roots in detectible amounts.
The common mussel, Mytilus edulis, reportedly took up alpha and beta-
endosulfan differentially, although the same study suggested that en-
dosulfan was not absorbed directly from seawater by the mussel, but
rather was taken up with suspended particles to which it was adsorbed
(Roberts 1975).  When pigs were fed an acute oral dose of 2 ppm, organ
residues after 27, 54, and 81 days were reportedly insignificant com-
pared to organ residues of DDT in pigs fed seven ppm of the latter.
Exact residues were not available, however (Maier-Bode 1966).
                                  339

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Volatilization-
Endosulfan volatilized more readily from glass than from leaf surfaces,
and more readily from sugar beet foliage than from bean foliage.  Under
controlled laboratory conditions, endosulfan isomers and metabolites
volatilized from glass in the order:  alpha isomer > ether > beta isomer
> sulfate > diol but at the higher temperatures of the greenhouse, the
order was:  alpha isomer > ether > beta isomer > diol > sulfate (Beard
and Ware 1969).
Persistence-
Endosulfan is an infrequently found residue in agricultural soils of
southern Ontario (Harris ^ al.  1966).  Stevens et^ al. (1970) found
endosulfan residues in one third of soils with a history of regular
pesticide usage (vegetable, cotton, forest), and in nine percent of
soils with a history of little or no pesticide use (root vegetables,
grains).  Residues in vegetable/cotton soils were as high as 1.22 ppm;
in forests as high as 4.63 ppm;  in grain/root crop soils as high as
0.92 ppm.  Mullins et^ a^. (1971) found endosulfan in only one of fifty
randomly selected Colorado soils, even though forty-one of the soils
contained pesticide residues.
When soil was treated with 6.7 kg/ha of endosulfan, 50 percent of the
alpha isomer was converted to endosulfan sulfate within 60 days.  The
beta isomer required 800 days for 50 percent conversion to endosulfan
sulfate  (Stewart and Cairns 1974) .  The sulfate was characterized by
the authors as being equally toxic to insects and "relatively stable",
but no persistence times for it were given.  Residues of endosulfan
sulfate, (0.3 ppm), fceta-endosulfan  (0.06 ppm) and aIpha-endosulfan
(0.01 ppm) were found in potato peels, and 0.03 ppm endosulfan sulfate
in the potato pulp.  The authors concluded that conversion to endosul-
fan sulfate occurred in the potato (Stewart and Cairns 1974) .
When one Ib/A (0.89 kg/ha) of granular endosulfan was applied to Ber-
muda grass, 13.7 percent remained after 96 days, during which two crops
                                  340

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of hay were cut and 16.5 inches of rain fell  (Byers £t^ a^. 1965).  In
flooded rice fields of east Java, agricultural levels of endosulfan
(1.4 liter of Thiodan 35 EC in 750 liters of water per hectare) resulted
in elevated endosulfan levels for no more than five days.  Maximum le-
vels in mud were 1.9 ppm (Gorbach et_al. 1971).  Greve and Verschuuren
(1971) reported endosulfan residues of up to 0.07 ppb in river water,
and up to 0.01 ppb in drinking water.  Greve and Wit  (1971) estimated
a half-life of five weeks for endosulfan in water at pH 7, but of five
months at pH 5.
Effects on Non-Target Species-
Microorganisms—Gorbach and Knauf (1971) did not find any inhibition
of bacterial action by endosulfan under field conditions.  Knauf and
Schulze (1973), however, noted that the aquatic microorganism CTzZoreZZa
Vulgaris responded to 0.2 ppm of endosulfan by reducing its rate of re-
production.
Invertebrates—Luedemann and Neumann (1962) studied the effects of en-
dosulfan on ten aquatic invertebrates.  Mussels (Dvei-ssend) were unaf-
fected by less than ten ppm and killed by 100 ppm endosulfan while the
American river crab (Cambarus affinis) was affected by 0.1 ppm and kil-
led by one ppm.  Most sensitive was the flea crab (Cayinogrammarus).
which was killed by 0.005 ppm, with toxic effects noted at 0.001 ppm.
Fish and amphibians—Endosulfan is highly toxic to fish.  Gorbach and
Knauf (1971) considered the lethal levels to be between 0.001 and 0.01
ppm, depending on the species.  Toor et al. (1973) found 0.007 ppm to
be the threshold level of endosulfan toxicity in carp, while 0.005 ppm
was the maximum sublethal dose.  Rainbow trout fry were adversely af-
fected by 0.006 ppm and pike by 0.001 ppm endosulfan, while the lethal
levels were 0.01 ppm and 0.005 ppm for the two species, respectively
(Leudemann and Neumann 1962).  Greve and Wit  (1971) considered one ppb
to be a sufficiently great concentration of endosulfan to cause large
fish kills under unfavorable conditions.  Schoettger  (1970) reported
                                  341

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TL,./, levels of endosulfan to be as low as 0.3 ppb in trout, but noted
that trout eggs could tolerate 50 ppm for two hours.  Endosulfan at
one Ib/A (1.12 kg/ha) was toxic to the toad Bufo boreas  (Mulla et al.
1963).
Birds—The LD_Q of endosulfan for starlings was 35 mg/kg  (Schafer 1972):
for mallards, 200 to 705 mg/kg, and for ring-necked pheasants, 620 to
1000 mg/kg (Martin 1968).  In tests on chicken and quail  embryos, nei-
ther immersion of the eggs nor injection of the embryos with endosul-
fan caused birth defects, but sterility occurred in both  males and fe-
males so treated (Lutz-Ostertag and Kantelip 1971).
Mammals—The LD ~ of endosulfan to rats was 100 mg/kg (Schafer 1972).
In mice, the acute oral LD   was estimated at 15 mg/kg in highly inbred
(Balb/c) mice; chronic dietary intake of ten ppm was sublethal (Deema
et al. 1966).  Diet was found to affect tolerance to endosulfan in
rats, which had an acute oral LD,.., of 5.1 + 1.4 mg/kg endosulfan if  fed
a protein-deficient diet; when casein constituted 81 percent of the
diet, the LDC_ rose to 98 + 7 mg/kg endosulfan (Eldon et  al. 1970).
            _>u            —                           	
Endosulfan was the only chlorinated hydrocarbon insecticide found not
to be accumulated in mammals (Vettorazzi 1975).
                                  342

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Toxaphene
Toxaphene is the name for a mixture of chlorinated camphene compounds
of uncertain identity, with a chlorine content of 67 to 69 percent by
weight.  It was introduced by Hercules Powder, Inc. in 1948 and is
used heavily on cotton, formerly with DDT and now with methyl para-
thion or parathion.  Other names for toxaphene include polychlorocam-
phene (USSR), chlorinated camphene, and octachlorocamphene.  It is
similar in composition and origin to several other chlorinated terpenes,
such as strobane.  Toxaphene is the most widely used chlorinated hy-
drocarbon insecticide (Matsumura et al. 1975).
Toxaphene is a yellow waxy solid with a mild terpene odor which softens
between 70  and 90 C.  It is noncorrosive in the absence of moisture,
and its solubility in water is 0.4 ppm (La Fleur 1974, Metcalf and San-
born 1975).  It is readily soluble in organic solvents, including pet-
roleum oils, and can be dehydrochlorinated by heat, strong sunlight,
and by certain catalysts such as iron (Martin 1968) .
Bevenue and Beckman (1966) considered gas chromatography to be an un-
reliable method of identifying toxaphene if other pesticides were pre-
sent.  The alternatives, total chloride determination and bioassay, are
hardly specific to toxaphene, and so are limited to situations in which
the history of contamination is known (Guyer et al. 1971) .  Kawano e_t_
al. (1969) reported that a mixture of sulfuric-fuming nitric acid can
be used to remove parathion and DDT from samples before analyses for
toxaphene.
Despite prolonged and heavy use, relatively little is known of the ac-
tion or fate of toxaphene in the environment, since the complexity of
its composition makes residue analyses tedious and uncertain (Guyer et
al. 1971).  Nelson and Matsumura (1975) circumvented the analytical
                                  343

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difficulties by constructing a simplified toxaphene, consisting of a
few toxaphene components, but this approach is restricted to laboratory
experiments.  Isolation of some major components of toxaphene was a-
chieved recently by Matsumura et al. (1975) who elucidated the struc-
ture of two toxaphene components which were said to account for up to
56 percent of the mixture's toxicity to mammals.  Casida and his co-
workers established that toxaphene consists of at least 175 polychlor-
inated derivatives of camphene, one of which was identified as 2,2,5-
end^o, 6-exOj8,9,10-heptachlorobornane, shown in Figure 16 (Casida et al.
1974,  Holmstead et_ al. 1974, Palmer et_ al. 1975).  An octachloronor-
bornane constituting six percent of the mixture was isolated and was
found to be fourteen times as toxic to mammals as toxaphene (Khalifa
e_t_ ai^. 1974).  Anagnostopoulos, Parlar, and Korte (1974) also isolated
several toxaphene components, of which three are shown in Figure 15.
Together these constituted five to eight percent of technical toxaphene.
Degradation-
Biological—rats fed 20 mg/kg   Cl-toxaphene excreted about 37 percent
of the radioactivity unchanged in the feces, but 15 percent was excre-
ted in the urine, mostly as ionic chloride.  Repeated doses led to de-
creases in the fecal, or unmetabolized, fraction (Crowder and Dindal
1974).  Ohsawa et al. (1975) found half the radioactivity in the urine
as chlorides, and concluded that biodegradability was characteristic
of all toxaphene fractions, but that relatively few of the fractions
were toxic to the rat.
In dairy cattle, lactating cows fed up to 20 ppm toxaphene for 77 days
excreted it in their milk for only fourteen days, after the end of the
treatment, but a single cow who was nearly dry excreted toxaphene in
her milk for longer periods.  The authors concluded that excretion in
milk was a major route of toxaphene elimination in cattle (Zweig et al.
1963).  There were no data available on the degradation of toxaphene
by microorganisms, plants or invertebrates.
                                   344

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2,2.,5-ENDO, 6-EXO, 8, 9,10-HEPTA-
CHLOROBORNANE~TTASIDA ET AL.  1974)
(ANAGNOSTOPOULOS  ET AL. 1974)
         CLCH2
                    CL

 (ANAGNOSTOPOULOS ET AL,  1974)
                                            CL
  (ANAGNOSTOPOULOS  ET AL, 1974)
                    STRUCTURES  OF  TOXAPHEME  COMPONENTS
                           Figure 15
                                  345

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Chemical and physical—Clay-catalyzed decomposition of toxaphene is
purportedly mediated by acidic diluents of the clays and increasing
temperature as well as increasing acidity speeded the degradation (Fow-
ker et al. 1960).  Physical degradation of toxaphene has not been re-
ported on.  Inasmuch as toxaphene consists of mixed chlorinated cam-
phenes, it seem plausible that degradative methods safe for DDT and cy-
clodiene insecticides would be safe for use with toxaphene.  Iron is
known to catalyze dehydrochlorination of toxaphene (Martin 1968) .
Transport-
Studies on transport are difficult because of the complexity of the
mixture and the difficulty of identifying small quantities of the mul-
titudinous components.  Bradley and co-workers (1972) recovered less
than one percent of the toxaphene applied to cotton plots in the sur-
face runoff water; of the toxaphene lost to water flow, 75 percent was
associated with sediment.  After ten years, up to 95 percent of the
toxaphene residues remaining in Houston black clay were in the top 12
inches of soil (Swoboda e_t_ al. 1971) .  Toxaphene applied to Dunbar soil
in a South Carolina field plot was found in ground water within two
months however.  The half-life in soil was estimated to be 120 days,
but groundwater contamination persisted for the entire year of obser-
vation (La Fleur et al. 1972).  Toxaphene is also a contaminant of the
lower Mississippi and its tributaries (Barthel et al. 1969) .  Further-
more, traces of two heptachloronorbornenes which could be degradation
products of toxaphene have been found in New Orleans drinking water at
levels of 0.04 to 0.06 ppb (ANON. 1974).  Klein and Link (1967) found
that when toxaphene was sprayed on kale, most of the pesticide disap-
peared within three days, even in the absence of rain: after seven days
and two inches of rain, only eight percent remained on the leaves and
after 28 days, only traces were found.
Weith and Lee (1971) observed that toxaphene residues in the top five
centimeters of lake sediment increased for 190 days following treatment,
                                  346

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and then decreased by a factor of two every 120 days, apparently by
transport to deeper strata; a rate of movement of 0.4 to 1.1 centime-
ters per day was estimated.  Toxaphene was not, however, detected be-
low 20 centimeters.  Lake water did not leach toxaphene out of sediment
under laboratory conditions.
When a toxaphene-contaminated stream was dredged, toxaphene residues
increased in estuarine fauna and flora.  Oysters  (Crassostrea
ca) contained two to five ppm, but mummichogs (Fundulus
contained more than 200 ppm toxaphene.  Even marsh grass (Spart~ina al-
termiflora} contained 7.5 ppm toxaphene, providing a rare example of
transport of toxapbene from soil into plants.  The authors postulated
that uptake by the marsh grass was facilitated by the species' ability
to transport and accumulate salt (Reimold and Durant 1974).  Adsorption
on charcoal decreased the toxicity of toxaphene to goldfish (Barren
1969).
When toxaphene was studied in an aquatic terrestrial ecosystem (Metcalf
et_ _al_. 1971), algae, snails, and mosquitofish were found to contain
                                                     14
6902-fold, 9600-fold, 890-fold and 4247-fold as much   C-toxaphene,
respectively, as was found in the water, indicating that toxaphene is
highly accumulative in aquatic food chains (Sanborn and Metcalf 1975).
Persistence-
After 16 years, residues of toxaphene in Congaree sandy loam were es-
timated at 49 percent (Nash and Harris 1973).  After 14 years under
conditions predisposing to maximum persistence, 45 percent remained in
the soil (Nash and Woolson 1967).  Randolph ett_ al_. (1960), however, ob-
served a loss of 50 percent of toxaphene in one year in Texas soils.
The data in these studies included DDT residues similar to those re-
ported for toxaphene.
When toxaphene was applied for five years to a California soil, the
total application reached 103.6 Ibs/A (116 kg/ha), with soil residues
                                  347

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of ten to 15 ppm after the fifth application.  Four years later, four
to six ppm remained, a loss of approximately 60 percent over four years
(Hermanson et al. 1971) .
Persistence of toxaphene in lakes was found to depend heavily on the
nature of the lake:  shallow eutrophic lakes were successfully restock-
ed with fish after one year, whereas deep, oligotrophic lakes were
still toxic after five years (Terriere et_ al. 1966).  Levels of toxa-
phene were 88 ppb in treatment of the shallow lake:  one year later,
water levels had fallen to one ppb, but aquatic plants contained 500
ppb, aquatic animals (other than fish) 1,000 to 2,000 ppb, and trout
contained up to 20,000 ppb.  Similar levels were observed in trout from
the deep lake with sparse biota (Terriere et al. 1966).  Similar re-
sults were obtained by Johnson et al. (1966), who concluded that sorp-
tion rather than degradation of toxaphene was responsible for the
detoxification of toxaphene in eight Wisconsis lakes.
Effects on Non-Target Species-
Microorganisms—When pure cultures of marine phytoplankton were grown
in the presence of pesticides, toxaphene at 0.15 ppm was absolutely
toxic, preventing growth in all species tested.  Even 0.01 ppm depres-
sed growth in all species except the rather resistant Protocooous;
0.00015 ppm prevented all growth of Monoerysis lutheri,, the most sen-
sitive species in the group and 0.000015 ppm toxaphene still caused
78 percent growth inhibition in this species (Ukeles 1962).  At high
agricultural levels of application, toxaphene x^as reported to have sig-
nificant effect on the numbers of bacteria or fungi in soil within ten
months of five annual applications (Martin et al. 1959).  Smith and
Wenzel (1947) had reported stimulation of fungi and bacteria which
were able to use toxaphene for growth.
Plants—Cullinan (1949) observed degradation of toxaphene during tests
of phytotoxicity and soil effects.  Diaz-Mena (1954) also observed phy-
totoxicity with toxaphene, as with all chlorinated hydrocarbons, under
                                  348

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his experimental conditions.  Toxaphene reportedly inhibited photosyn-
thesis in alfalfa unless rain occurred within six days.  Increasing
temperature decreased the degree of inhibition  (Kralovic 1974) .
Invertebrates—Oysters  (Cras so street virgin-Lea)  exposed to one  ppb/liter
each of DDT, toxaphene, and parathion gained less wieght and were more
subject to mycelial fungal infections than control oysters, while other
single pesticides at one ppb did not have any discernible effect  (Lowe
et_ al. 1970).  Hard shell clams (Meroenaria meroena.ria) and oysters
(Cras so street. viTginiaa) were more affected by toxaphene during the em-
bryonic than larval stage (Davis and Hidu 1969).
Fish and amphibians—Toxaphene is among the most toxic of pesticides
to fish; with only rotenone and endrin acknowledged to be more toxic
(Adlung 1957).  Little  species difference was observed in the  relative
sensitivities of fish families to toxaphene:  comparisons were made be-
tween Ictaluridae3 Cyprinidae3 Centrarchidae, and Salmonidae (Macek and
McAllister 1970).  Toxaphene was more toxic to  mosquitofish in static
than in flowing solutions (Burke and Ferguson 1969) .  Toxaphene accu-
mulation was found in bluegills (Lepomis macrochirus) after treating
lakes for rough fish control even though the restocked bluegills grew
well (Hughes and Lee 1973).
In fathead minnows (Pimephales promelas), water levels of 55 to 1,230
ng/liter (0.055 ppb to  1.23 ppb) resulted in growth disturbance after
90 and within 150 days; the minnows' collagen content was shown to de-
crease, both absolutely and in relation to calcium content, and the in-
creased mineralization was expressed by increased fragility.   Under
stress, toxaphene-treated minnows' backbones fractured (ITehrle and
Mayer 1975a).  Brook trout (Salvelinus fontinalis) were exposed to to-
xaphene from 22 days before to ninety days after hatching.  Although
hatching itself was not affected, growth was significantly decreased
by 139 and 288 ng/liter (0.137 to 0.288 ppb) within 30 days, and by
39 ng/liter (0.039 ppb) within ninety days after hatching.  Whole-body
                                  349

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collagen was decreased within 15 days of hatching, and calcium and
phosphorus content increased (Mehrle and Mayer 1975b) .
Toxaphene was less toxic to anuran amphibians than were endrin, aldrin,
or dieldrin, and had approximately the same toxicity as DDT  (Ferguson
and Gilbert 1967).  Tolerance of up to 200-fold was found in amphibians
near insecticide treated cotton fields (ibid).
Birds—The !!)_„ of toxaphene in seven-day old mallard ducklings was
30.8 mg/kg, with 95 percent confidence limits of 23.3 to 40.6 mg/kg
(Tucker and Crabtree 1970).  Mallards were less sensitive at three to
five months of age, with an LD,-^ of 70.7 mg/kg and 95 percent confidence
limits of 37.6 to 133 mg/kg.  Mature sharp-tailed grouse had an W)rn of
10-2C mg/kg.  Symptoms were seen within 20 minutes in some species, but
mortality generally occurred between two and fourteen days (Tucker and
Crabtree 1970).
Limited tests with young chickens suggested that toxaphene, in contrast
to Ojp'-DDT and p^p'-DDE, decreased sleeping time (Stickel 1973).  Tox-
aphene increased the thyroid growth of bobwhite quail when birds were
treated with 50 ppm for three or four months while liver weights did
not increase even after 500 ppm were fed for the same length of time
(Hurst e^ al. 1974).
Mammals—The acute oral LD,.- of toxaphene in rats is g€;nerally consid-
ered to be 90 mg/kg in males and 80 mg/kg in females  (Servintuna 1963,
Guyer et_ al_. 1971) although Jones et_ al_. (1968) claimed an LD5Q of 283
mg/kg.  The dermal LD . was slightly over 1,000 mg/kg (Servintuna 1963,
Jones et al. 1968).  Schindler  (1956) found that toxaphene controlled
voles when applied at two kg/ha, and Lange and Crueger (1960) found
that four liters/ha of a 50 percent toxaphene solution resulted in a
thorough kill of field mice.
In rats, less than additive effects were reported for the combination
of carbofenthion, diazinon, or parathion with toxaphene, but carbaryl
                                  350

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or malathion interacted additively (Keplinger and Deichman 1967).   The
mode of action of toxaphene poisoning is not understood, but it is
thought to be pharmacologically similar to that of the cyclodienes,
since cyclodiene resistance invariably confers toxaphene resistance in
insects (Brooks 1974, Vol. 2).  No effects of toxaphene on rat repro-
duction were found during a multigeneration study (Kennedy et_ al.  1973)
                                  351

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Conclusions
Although data on organochlorine insecticides are by no means complete,
it is apparent that, in less than forty years, they have become almost
universal contaminants of land, water, and living things.  Of the 12
compounds for which a literature search was carried out, only methoxy-
chlor is biodegradable.  With respect to the other compounds, it must
be assumed:
     1.  that, over the period of their persistence, all will move
         through soil, into water, into the atmosphere, and into
         living organisms;
     2.  that there are no efficient biological pathways for their
         degradation to naturally occurring substances;
     3.  that the effects of some, and perhaps all, of these com-
         pounds on microorganisms, fish, birds, and even man may
         eventually prove as disastrous as they seemed benign or-
         iginally.
Accordingly, it is recommended that waste chlorinated hydrocarbon insec-
ticides be burned or chemically degraded, with suitable precautions for
disposal of chlorine and other toxic gases.  Disposal in soil, whether
in shallow pits or deep wells, is considered utterly undesirable, since
the available evidence is that dispersal would precede any significant
degradation.  The sole exception to these conclusions is methoxychlor,
which might be disposed of in flooded soil or in sequestered ponds,
provided adequate precautions were taken against contaminating natural
waters.  Endosulfan is not excepted from the conclusion against soil
or water disposal, since the few available data suggest that its major
terminal residue endosulfan sulfate, which shares most of the toxic
properties of endosulfan itself, is very persistent in soil.
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References
Achari, R. G., S. S. Sandhu and W. J. Warren; 1975.  Chlorinated hydro-
  carbon residues in groundwater.  Bull. Environ. Contain. Toxicol. 13:
  94-97.
Acree, F., Jr., M. Beronza, M. C. Bowmman; 1963.  Codistillation of DDT
  with water.  J. Agric. Food Chem. 11:278-280.
Adlung, K. G. ; 1957.  Toxicity of insecticidal and acaricidal agents for
  fish.  Naturwissenschaften 44:471-472. (Chem. Abstr. 52:2325d, 1958).
Albone, E. S., G. Eglinton, N. C. Evans, J. M. Hunter, M. M. Rhead; 1972.
  Fate of DDT in Severn estuary sediments.  Environ. Sci. Technol. 6:
  914-918.
Albright, R., N. Johnson, T. W. Sanderson, R. M. Farb, R. Melton, L.
  Fisher, G. R. Wells, W. R. Parsons, V. C. Scott, J. L. Speake,  J. R.
  Stallworth, B. G. Moore and A. W. Hayes; 1974.  Pesticide residues in
  the topsoil of five west Alabama counties.  Bull. Environ. Contain.
  Toxicol. 12:378-384.
Alexander, M.; 1972.  in:Environmental Toxicology of Pesticides3 pp. 365-
  383.  F. Matsumura, G. M. Boush, and T. Misato, Eds.; Academic Press.
  N. Y.; Microbial degradation of pesticides.
Alley, E. G. and B. R. Layton; 1974.  Identification of insecticide
  photoproducts by mass spectrometry.  Mass Spectram. NMR Spectrosc.
  Pestic. Chem., Proc. Symp. 1973 81-90. (Chem. Abstr. 81:119540-, 1974).
Alley, E. G., D. A. Dollar, B. R. Layton, and J. P. Minyard, Jr.; 1973.
  Photochemistry of mirex.  J. Agr. Food Chem. 21:138-139.
Alley, E. G., B. R. Layton and J. P. Minyard; 1974.  Identification of
  the photoproducts of the insecticides mirex and kepone.  J. Agr. Food
  Chem. 22:442-445.
Anagnostopoulos, M. L., H. Parlar, F. Korte; 1974.  Beitrage zur okolo-
  gischen Chemie LXXI.  Isolierung, Identifizierung, und Toxikologie
  einiger Toxaphenkomponenten.  Chemosphere 3:65-70.
                                  353

-------
Anderson, J. P. E.,  E. P. Lichtenstein, W. F. Whittingham; 1970.  Effect
  of Muaor altemans on the persistence of DDT and dieldrin in culture
  and in soil.  J. Econ. Entomol. 63:1595-1599.
Andrade, P. S. L., Jr. and W. B. Wheeler; 1974.  Biodegradation of mirex
  by sewage sludge organisms.  Bull. Environ. Contam. Toxicol. 11:415-
  416.
Anonymous; Nov. 1974.  Draft Analytical Report.  New Orleans Area Water
  Supply.  U.S. Environmental Protection Agency Region VI Dallas, Tx.
  28 pp.
Archer, T. E.; 1970.  Kelthane residues on almond hull meal exposed to
  ultraviolet light  irradiation.  Bull. Environ. Contam. Toxicol. 5:247-
  250.
Archer, T. E.; 1974.  Effect of ultraviolet radiation filtered through
  pyrex glass upon residues of dicofol (kelthane; l,l'-bis(p-chloro-
  phenyl)-2,2,2-trichloroethanol) on apple pomace.  Bull. Environ. Con-
  tam. Toxicol. 12:202-203.
Archer, T. E., I. K. Nazer, and D. G. Crosby; 1972.  Photodecomposition
  of endosulfan and related products in thin films by ultraviolet light
  irradiation.  J. Agr. Food Chem. 20:954-956.
Asai, R. I., W. E. Westlake and F. A. Gunther; 1969.  Endrin decomposi-
  tion on air-dried soils.  Bull. Environ. Contam. Toxicol. 4:278-284.
Askerov, N. A.; 1969.  Effect of insecticides on the number of some
  groups of soil microorganisms.  Biol. Zh. Arm. 22:106-107. (Chem. Abstr.
  71:122761k, 1969).
Atabaev, S. T., Y. U. Khasanov and L. S. Nazarova; 1970.  Stability of
  the pesticide aldrin under hot climate conditions.  Gig. Sanit. 35:
  108-109.  (Chem. Abstr. 73:34140t, 1970).
Atwal, 0. S.; 1973.   Fatty changes and hepatic cell excretion in avian
  liv^r:  an electron microscopical study of kepone toxicity.  J. Comp.
  Pathol. 83:115-124.
Bache, C. A., G. G.  Gyrisco, S. N. Fertig, E. W. Huddleston, D. J. Lisk,
  F. E. Fox, G. W. Trimberger and F. R. Holland; 1960.  Effects of
                                   354

-------
  feeding low levels of heptachlor epoxide to dairy cows on residues
  and off-flavors in milk.  J. Agr. Food Chem. 8:408-409.
                                                                 14
BSckstrb'm, J. , E. Hansson and S. Ullberg; 1965.  Distribution of   C-
          14
  DDT and   C-dieldrin in pregnant mice determined by whole-body auto-
  radiography.  Toxicol. Appl. Pharmacol. 7:90-96.
Bailey, S., P. J. Bunyan, B. D. Rennison and A. Taylor; 1969a.  The
  metabolism of l,l-di(p-chlorophenyl)-2,2,2-trichloroethane and 1,1-di-
  (p-chlorophenyl)-2,2-dichloroethane in the pigeon.  Toxicol. Appl.
  Pharmacol. 14:13-22.
Bailey, S., P. J. Bunyan, B. D. Rennison and A. Taylor; 1969b.  The
  metabolism of l,l-di(p-chlorophenyl)-2,2-dichloroethylene and 1,1-di-
  (p-chlorophenyl)-2-chloroethylene in the pigeon.  Toxicol. Appl.
  Pharmacol. 14:23-32.
Baker, R. D. and H. G. Applegate; 1970.  Effect of temperature and ul-
  traviolet radiation on the persistence of methyl parathion and DDT in
  soil.  Agron. J. 62:509-512.
Balaban, I. E. and F. K. Sutcliffe; 1945.  Thermal stability of DDT.
  Nature 155:755.
Baldwin, M. K. and J. Robinson; 1969.  Metabolism in the rat of the
  photoisomerization product of dieldrin.  Nature 224:283-284.
Balinov, I.; 1973.  Determination of residual amounts of DDT and its
  metabolic products in apple orchards.  Gradinar. Lozar. Navka 10:43-
  50. (Chem. Abstr. 81:164644m, 1974).
Ballard, T. M. ; 1971.  Role of humic carrier substances in DDT movement
  through forest soil.  Soil Sci. Soc. Amer., Proc. 35:145-147.
Baluja-Marcos, G. and L. Serrano Gonzalvez; 1970.  Contamination of the
  environment by organic pesticides.  V. Adsorption-desorption of lin-
  dane and aldrin by two types of Spanish agricultural soils.  Rev. Ag-
  roquim. Tecnol. Aliment. 10:486-498. (Chem. Abstr. 75:97534m, 1971).
Bardiya, M. C. and A. C. Gaur; 1968.  Influence of insecticides on car-
  bon dioxide evolution from soil.  Indian J. Microbiol. 8:233-238.
  (Chem. Abstr. 72:65739d, 1970).
                                  355

-------
Barlow, F.; 1966.  Spontaneous decomposition of a sample of pure endrin.
  Nature 212:505.
Barlow, F. and A. B. Hadaway; 1958.  Aqueous suspensions of insecti-
  cides.  VI. Sorption of insecticides by soils.  Bull. Entomol. Res.
  49:315-331.
Barnes, J. M.; 1966.  Carcinogenic hazards from pesticide residues.
  Residue Reviews 13:69-82.
Barnett, J. R. and H. W. Borough; 1974.  Metabolism of chlordane in rats.
  J. Agr. Food Chem. 22:612-619.
Barren, J. C.; 1969.  Adsorption of toxaphene by activited charcoal.
  Tex. J. Sci. 21:99-100.
Bartha, R., R. P. Lanzilotta and D. Pramer; 1967.  Stability and effects
  of some pesticides in soil.  Appl. Microbiol. 15:67-75.
Barthel, W. F.,  J. C. Hawthorne, J. H. Ford, G. C. Bolton, L. L. McDow-
  ell, E. H. Grissinger and  D. A. Parsons; 1969.  Pesticide residues
  in sediments of the lower  Mississippi river and its tributaries. Pes-
  tic. Monit. J. 3:8-66.
Bartsch, H., C.  Malaveille and R. Montesano; 1975.  In vitro metabolism
  and microsome-mediated mutagenicity of dialkylnitrosamines in rat,
  hamster, and mouse tissues.  Cancer Res. 35:644-651.
Beall, M. L., Jr., and R. G. Nash; 1969.  Crop seedling uptake of DDT,
  dieldrin, endrin, and heptachlor from soils.  Agron. J. 61:571-575.
Beard, J. E. and G. W. Ware; 1969.  Fate of endosulfan on plants and
  glass.  J. Agron. Food Chem. 17:216-220.
Begum, S., S. Gaeb, H. Parlar and F. Korte; 1973.  Beitrage zur bkolo-
  gischen Chemie LXIV.  Reaktionsverhalten von Kelevan in L&'sung, als
  FestkSrper und in der Gasphase bei UV-Bestrahlung.  Chemosphere 2:
  235-238.
Beitz, H., J. Hartisch, F. Seefeld, and E. Heinisch; 1970.  Uptake of
  DDT from the soil by plants.  Arch. Pflanzenschutz 6:99-112. (Chem.
  Abstr. 74:52432q, 1971).
                                   356

-------
Bender, M. E. and P. Eisele; 1971.  Long term effects of pesticides on
  stream invertebrates.  Nat'l. Tech. Inf. Serv. PB-206, 692.
Bennett, G. W.,  D. L. Bailee, R. C. Hall, J. E. Faney, W. L. Butts, J.
  V. Osmun; 1974.  Persistence and distribution of chlordane and diel-
  drin applied as termiticides.  Bull. Environ. Contam. Toxicol. 11:64-
  69.
Benson, W. R.; 1971.  Photolysis of solid and dissolved dieldrin.  J.
  Agr. Food Chem. 19:66-72.
Beran, F. and J. A. Guth; 1965.  Das Verhalten Organischer insektizider
  Stoffe in verschiedenen Boden mit besonderer Berlicksichtigung der
  Mb'glichkeiten einer Grundwasserkontamination.  Pflanzenschutz Ber.
  33:65-117.
Bess, H. A. and J. W. Hylin; 1970.  Persistence of termiticides in
  Hawaiian soil.  J. Econ. Entomol. 63:633-638.
Bevenue, A. and H. Beckman; 1966.  The examination of toxaphene by gas
  chromatography.  Bull. Exp. Contam. Toxicol. 1:1-15.
Bevenue, A., J.  W. Hylin, Y. Kawano and T. W. Kelley; 1972a.  Pesticides
  in water.  Pestic. Monit. J. 6:56-64.
Bevenue, A., J.  N. Ogata and J. W. Hylin; 1972b.  Organochlorine pes-
  ticides in rainwater, Oahu, Hawaii, 1971-1972.  Bull. Environ. Contam.
  Toxicol.  8:238-241.
Bidleman, T. F.  and C.  E. Olney; 1974.  Chlorinated hydrocarbons in the
  Sargasso Sea atmosphere and surface water.  Science  183:516-518.
Bixby, M. W., G. M. Boush and F. Matsumura; 1971.   Degradation of diel-
  drin to carbon dioxide by a soil fungus Tviehoderma koningii.   Bull.
  Environ. Contam. Toxicol. 6:491-494.
Block, S. S.; 1968.  Antibacterial and antifungal  activity of kepone de-
  rivatives.  Develop.  Ind. Microbiol. 9:430-436.  (Chem. Abstr.  69:2045s,
  1968).
Bollen, W. B., H. E. Morrison and H.  H. Crowell; 1954.  Effect of field
  and laboratory treatments with BHC and DDT on nitrogen transformations
  and soil respiration.  J. Econ. Entomol. 47:307-312.
                                   357

-------
Bollen, W. B., J. E. Roberts and H. E. Morrison; 1958.  Soil properties
  and factors influencing aldrin-dieldrin recovery and transformation.
  J. Econ. Entomol. 51:214-219.
Bollen, W. B. and C. M. Tu; 1971.  Influence of endrin on soil microbial
  populations and their activity.  U.S. Forest Serv., Res. Pap. PNW-
  114, 4 pp. (Chem. Abstr. 76:767z, 1972).
Boswell, V. R.;  1955.  Effects of certain insecticides in soil on crop
  plants.  U.S.  Dept. Agr. Tech. Bull. 1121, 59 pp. (Chem. Abstr. 49:
  16316c, 1955).
Boucher, F. R. and F. G. Lee; 1972.  Adsorption of lindane and dieldrin
  pesticides on unconsolidated aquifer sands.  Environ. Sci. Technol.
  6:538-543.
Bourquin, A. W., S. K. Alexander, H. K. Speidel, J. E. Mann and J. F.
  Fair; 1972.  Microbial interactions with cyclodiene pesticides.
  Develop. Ind.  Microbiol. 13:264-276.
Bowman, M. C., M. S. Schechter and R. L. Carter; 1965.  Behavior of
  chlorinated insecticides in a broad spectrum of soil types.  J. Agr.
  Food Chem. 13:360-365.
Bradley, J. R.,  T. J. Sheets and M. D. Jackson; 1972.  DDT and toxa-
  phene movement in surface water from cotton plots.  J. Environ. Qual.
  1:102-105.
Bradshaw, J. S., E. L. Loveridge, K. P. Rippee, J. L, Peterson, D. A.
  White, J. R. Barton and D. K. Fuhriman; 1972.  Seasonal variations in
  residues of chlorinated hydrocarbon pesticides in the water of the
  Utah Lake drainage system, 1970 and 1971.  Pestic. Monit. J. 6:166-
  170.
Breidenbach, A.  W., C. G. Gunnerson, F. K. Kawahara, J. J. Lichtenberg
  and R. S. Green; 1967.  Chlorinated hydrocarbon pesticides in major
  river basins 1957-1965. Pub. Health Repts. 82:139-156.
Brewerton, H. V. and D. A. Slade; 1964.  Kepone residues on applies.  New
  Zealand J. Agr. Res. 7:647-653.
Brooks, G. T.; 1971.  in:  Pesticide Terminal Residues, pp. 111-136.
                                   358

-------
  A. S. Tahori, Ed.  Butterworths, London.  The fate of chlorinated
  hydrocarbons in living organisms.
Brooks, G. T.; 1974.  Chlorinated Insecticides, 2 Vols. CRC Press,
  Cleveland.
Brown, A. L.; 1954.  Effect of several insecticides on ammonification
  and nitrification in two neutral alluvial soils.  Soil Sci. Soc. Amer.,
  Proc. 18:417-420.
Brown, J. R.; 1972.  Effect of dietary kelthane on mouse and rat repro-
  duction.  Pestic. Chem., Proc. Int. Congr. Pestic. Chem., 2nd; 6:
  531-548. (Chem. Abstr. 80:604b, 1974).
Brown, J. R., H. Hughes and S. Viriyanondha; 1969.  Storage, distribu-
  tion and metabolism of l,l-bis(4-chlorophenyl)-2,2,2-trichloroethanol.
  Toxicol. Appl. Pharmacol. 15:30-37.
Brown, L. R., E. G. Alley and D. W. Cook; 1975.  Effect of mirex and
  carbofuran on estuarine microorganisms.  U.S. Environ. Prot. Agency,
  Off. Res. Dev., (Rep.) EPA.  EPA 660/3-75-024.  47 pp. (Chem. Abstr.
  83:189038w, 1975).
Bruce, W. N. and G. C. Decker; 1966.   Insecticide residues in soybeans
  grown in soil containing various concentrations of aldrin, dieldrin,
  heptachlor, and heptachlor epoxide.  J. Agr. Food Chem. 14(4):395-398.
Bruce, W. N., G. C. Decker and J. G.  Wilson; 1966a.  The relationship
  of the levels of insecticide contamination of crop seeds to their fat
  content and soil concentration of aldrin, heptachlor, and their ep-
  oxides.  J. Econ. Entomol. 59:179-181.
Bruce, W. N. , R. P. Link, and G. C. Decker; 1966b.  Storage of hepta-
  chlor epoxide in the body fat and its excretion in milk of dairy
  cows fed heptachlor in their diets.  J. Agr. Food Chem. 13:63-67.
Burge, W. D.; 1971.  Anaerobic decomposition of DDT in soil:  accelera-
  tion by volatile components of alfalfa.  J.  Agr. Food Chem. 19:375-
  378.
Burke, W. D. and D. E. Ferguson; 1969.  Toxicities of four insecticides
  to resistant and susceptible mosquito fish in static and flowing so-
  lutions.  Mosquito News 29:96-101.
                                   359

-------
Burkhardt, C. C. and M. L. Fairchild; 1967.  Bioassay of field-treated
  soils to determine bioactivity and movement of insecticides.  J. Econ.
  Entomol. 60:1602-1610.
Burton, W. B. and G. E. Pollard; 1974.  Rate of photochemical isomeri-
  zation of endrin in sunlight.  Bull. Environ. Contain. Toxicol. 12:
  113-116.
Butcher, J. W., R. M. Snider and J. L. Aucamp; 1970.  Biology of selec-
  ted microarthropods and their role in DDT degradation.  Ann. Zool.-
  Ecol. Anim. 20 (suppl.):207-217.
Butler, G. L., T. R. Deason and J. C. O'Kelley; 1975.  Loss of five
  pesticides from cultures of twenty-one planktonic algae.  Bull.
  Environ. Contam. Toxicol. 13:149-152.
Butler, P. A., A. J. Wilson and A. J. Rick; 1960.  Effects of pesti-
  cides on oysters.  Proc. Natl. Shell Fisheries Assoc. 51:23-32.
  (Chem. Abstr. 57:5140a, 1962).
Byers, R. A., D. W. Woodham and M. C. Bowman; 1965.  Residues on coas-
  tal Bermuda grass, trash, and soil treated with granular endosulfan.
  J. Econ. Entomol. 58:160-161.
Cabejszek, I. and J. Stanislawska; 1965.  Effects of methoxychlor (1,1,1-;
  trichloro-2,2-bis(p-methoxyphenol) ethane) on water organisms.  Rocz-
  niki Panstwowego Zakladu Hig. 16:261-268. (Chem. Abstr,. 63:12259b,
  1965).
Cabral, J. R., M. C. Testa and B. Terracini; 1972.  Lack of long-term
  effects of the administration of heptachlor to suckling rats.  Tumori
  58:49-53.
Camoni, I., L. Gambetti, N. Gandolfo and G. Ramelli; 1971.  Organochlo-
  rine pesticide residues in soil and beets from the Agro Pontino re-
  gion.  Boll. Lab. Chim. Prov. 22:740-751. (Chem. Abstr. 77:18284v,
  1972).
Carlo, C. P., D. Ashdown and V. G. Heller; 1952.  Persistence of para-
  thion, toxaphene, and methoxychlor in soil.  Oklahoma Agr. Expt. Sta.
  Tech. Bull. No. T-42, 11 pp.  (Chem. Abstr. 46:3707b, 1952).
                                   360

-------
Caro, J. H.; 1971.  Accumulation of dieldrin and heptachlor on corn
  leaves in and around a treated field.  J. Agr. Food Chem. 19:78-80.
Caro, J. H. and A. W. Taylor; 1971.  Pathways of loss of dieldrin from
  soils under field conditions.  J. Agr. Food Chem. 19:379-384.
Caro, J. H., A. W. Taylor and E. R. Lemon; 1971.  Int. Symp. Identifi-
  cation Meets.  Environ. Pollut.s 1971, pp. 72-77; B. Westley, ed. Nat'l
  Res. Counc. Can.; Ottawa, Ont.  Measurement of pesticide concentra-
  tions in the air overlying a treated field. (Chem. Abstr. 80:91961e,
  1974).
Carter, L. J.;  1974.  Cancer and the environment (I): A creaky system
  grinds on.  Science 186:239-242.
Carter, F. L. and C. A. Stringer; 1970a.  Residues and degradation pro-
  ducts of technical heptachlor in various soil types.  J. Econ. Entomol,
  63:625-628.
Carter, F. L. and C. A. Stringer; 1970b.  Soil moisture and soil type
  influence on the initial penetration by organochlorine insecticides.
  Bull. Environ. Contam. Toxicol. 5:422-428.
Carter, F. L. and C. A. Stringer; 1971.  Soil persistence of termite
  insecticides.  Pest Contr. 39(2):13-14, 16, 18, 20, 22.
Carter, F. L.,  C. A. Stringer and D. Heinzelman; 1971.  l-hydroxy-2,3-
  epoxychlordene in Oregon soil previously treated with technical hep-
  tachlor.  Bull. Environ. Contam. Toxicol. 6:249-254.
Casida, J. E.,  R. L. Holmstead, S. Khalifa, J. R. Knox, T. Ohsawa, K. J.
  Palmer and R. Y. Wong; 1974.  Toxaphene insecticide:  a complex bio-
  degradable mixture.  Science 183:520-521.
Castro, T. F. and T. Yoshida; 1971.  Degradation of organochlorine in-
  secticides in flooded soils in the Phillipines.  J. Agr. Food Chem.
  19:1168-1170.
Castro, T. F. and T. Yoshida; 1974.  Effect of organic matter on the
  biodegradation of some organochlorine insecticides in submerged soils.
  Soil Sci. Plant Nutr. (Tokyo) 20:363-370. (Chem. Abstr. 82:165850h,
  1975).
                                  361

-------
Cecil, H. C., J. Bitman, and S. J. Harris; 1971.  Estrogenicity of
  o.,p'-DDT in rats.  J. Agr. Food Chem. 19:61-65.
Cecil, H. C., S. J. Harris, J. Bitman and P. Reynolds; 1975.  Estro-
  genic effects and liver microsomal enzyme activity of technical meth-
  oxychlor and technical l,l,l-trichloro-2,2-bis(p-chlorophenyl)ethane
  in sheep.  J. Agr. Food Chem. 23:401-404.
Ceurvels, A. R. , J. DerHovanesian, Jr. and J. Kaylor; 1974.  Ionizing
  radiation-induced changes in chlorinated hydrocarbons.  Mar. Pollut.
  Bull. 5:143-144.
Chacko, C. I. and J. L. Lockwood; 1967.  Accumulation of DDT and dieldrin
  by microorganisms.  Can. J. Microbiol. 13:1123-1126.
Chacko, C. I., J. L. Lockwood and M. Zabik; 1966.  Chlorinated hydro-
  carbon pesticides: degradation by microbes.  Science 154:893-895.
Chandra, P.; 1967.  Progr. Soil Biol.f Proc. Colloq.  1966; pp. 320-
  330.  0. Graff, ed.; F. Vieweg and Sohn G. m. b. H., Brunswick.
  Effect of two chlorinated insecticides on soil microflora and nitri-
  fication process as influenced by different soil temperatures and
  textures.  (Chem. Abstr. 70:19196k, 1969).
Chapman, S. K. and K. C. Leibman; 1971.  Effects of chlordane, DDT, and
  3-methylchloranthrene upon the metabolism and toxicity of diethyl 4-C.
  nitrophenyl phosphorothionate (parathion).  Toxicol. Appl. Pharmacol.
  18:977-987.
Chawla, R. P. and S. L. Chopra; 1967.  Persistence of residues of DDT
  and BHC in normal and alkaline soils.  J. Res., Punjab Agr. Univ. 4:
  96-103. (Chem. Abstr. 68:11928p, 1968).
Chekal, V. N. and E. M. Yurovskaya; 1967.  Stability of some chloro-
  organic insecticides in the soil, and their effect on soil, micro-
  flora.  Gig. Naselennykh Mest 1967, 189-193. (Chem. Abstr. 70:2702z,
  1969).
Chernoff, N. , R. J. Kavlock, J. R. Kathrein, J. M. Dunn and J. K. Haseman;
  1975.  Prenatal effects of dieldrin and photodieldrin in mice and
  rats.  Toxicol. Appl. Pharmacol. 31:302-308.
                                   362

-------
Chisholm, D. and A. W. MacPhee; 1972.  Persistence and effects of some
  pesticides in soil.  J. Econ. Entomol. 65:1010-1013.
Chisholm, R. D., R. H. Nelson and E. E. Fleck; 1949.  Toxicity of DDT
  deposits as influenced by sunlight.  J. Econ. Entomol. 42:154-155.
Chopra, N. M.; 1966.  Persistence and degradation of heptachlor in some
  soils.  J. Econ. Entomol. 59:326-330.
Claborn, H. V., R. C. Bushland, H. D. Mann, M. C. Ivey, and R. D. Rade-
  leff; 1960a.  Meat and milk residues from livestock sprays.  J. Agr.
  Food Chem. 8:439-442.
Claborn, H. B., R. D. Radeleff and R. C. Bushland; 1960b.  Pesticide
  residues in meat and milk.  U.S. Dept. Agr. ARS 33-63:46.
Clark, D. R., Jr., and M. A. R. McLane; 1974.  Chlorinated hydrocarbon
  and mercury residues in woodcock in the United States 1970-1971.
  Pestic. Monit. J. 8:15-22.
Clark, J. M. ; 1974.  Mutagenicity of DDT in mice, Drosophila melanogas-
  te?j and Neurospora arassa.   Aust. J. Biol. Sci. 27:427-440.
Clausen, J., L. Braestrup and 0. Berg; 1974.  Content of polychlori-
  nated hydrocarbons in arctic mammals.  Bull. Environ. Contam. Toxicol.
  12:529-534.
Cleveland, F. P.; 1966.  Summary of work on aldrin and dieldrin toxi-
  city at the Kettering Laboratory.  Arch. Environ. Health 13:195-198.
Cliath, M. and W. F. Spencer;  1971.  Movement and persistence of diel-
  drin and lindane in soil as influenced by placement and irrigation.
  Soil Sci. Soc. Amer., Proc.  35:791-795.
Cliath, M. M. and W. F. Spencer; 1972.  Dissipation of pesticides from
  soil by volatilization of degradation products.  Lindane and DDT.
  Environ. Sci. Technol. 6:910-914.
Collins, H. L., J. R. Davis and G. P. Markin; 1973.  Residues of mirex
  in channel catfish and other aquatic organisms.  Bull. Environ. Con-
  tam. Toxicol. 10:73-77.
Cooley, N. R., J. M. Keltner and J. Forester; 1972.  Mirex and aroclor
  1254.  Effect on and accumulation by Tetrdhymena pyriformis strain W.
                                  363

-------
  J. Protozool. 19:636-638.
Cowley, G. T. and E. P. Lichtenstein; 1970.  Growth inhibition of soil
  fungi by insecticides and annulment of inhibition by yeast extract
  or nitrogenous nutrients.  J. Gen. Microbiol. 62:27-34.
Crosby, D. G. and K. W. Moilanen; 1974.  Vapor-phase decomposition of
  aldrin and dieldrin.  Arch. Environ. Contain. Toxicol. 2:62-74.
                                                36
Crowder, L. A. and E. F. Dindal; 1974.  Fate of   Cl-toxaphene in rats.
  Bull. Environ. Contain. Toxicol. 12:320-327.
Cullinan, F. P.; 1949.  Some new insecticides.  Their effect on plants
  and soils.  J. Econ. Entomol. 42:387-391.
Cutcomp, L. K.; 1947.  Thermal decomposition of DDT dispersed in water.
  J. Econ. Entomol. 40:444-445.
Czaplicki, E.; 1969.  Use of isotope-labeled pesticides in residue
  studies.  Biul, Inst. Ochr. Rosl. 44:263-267. (Chem. Abstr. 73:2905e,
  1970).
Dalton, S. A., M. Hodkinson and K. A. Smith; 1970.  Interactions be-
  tween DDT and river fungi.  I. Effects of p^p'-DDT on growth of aqua-
  tic hyphomycetes.  Appl. Microbiol. 20:662-666.
Datta, P. R., E. P. Laug, J. 0. Watts, A. K. Klein and M. J. Nelson;
  1965.  Metabolites in urine of rats on diets containing aldrin or
  dieldrin.  Nature 208:289-290.
Davis, H. C.; 1961.  Effects of some pesticides on eggs and larvae of
  oysters (Crassostrea vivginioa) and clams  (Venus mercenap-ia').  Com.
  Fisheries Rev. 23:8-23. (Chem. Abstr. 57:1325d, 1962).
Davis, H. C. and H. Hidu; 1969.  Effects of pesticides on embryonic
  development of clams and oysters, and on survival and growth of the
  larvae.  U.S. Fish Wildl. Serv., Fish. Bull. 67:393-404.
Davis, K. J. and 0. G. Fitzhugh; 1962.  Tumorigenic potential of aldrin
  and dieldrin for mice.  Toxicol. Appl. Pharmacol. 4:187-189.
Davison, K. L., J. H. Cox and C. K. Graham;  1975.  Effect of mirex on
  reproduction of Japanese quail and on characteristics of eggs from
  Japanese quail and chickens.  Arch. Environ. Contain. Toxicol. 3:84-
  95.
                                  364

-------
Dawidow, B., J. L. Radomski and R. Ely; 1953.  Excretion of heptachlor
  epoxide in milk of a dairy cow fed heptachlor.  Science 118:383-384.
Dean, B. J., S. M. A. Doak and H. Somerville; 1975.  The potential mu-
  tagenicity of dieldrin (HEOD) in mammals.  Food Cosmet. Toxicol. 13:
  317-323.
Decker, G. C., W. N. Bruce and J. H. Bigger; 1965.  The accumulation and
  dissipation of residues resulting from the use of aldrin in soils.  J.
  Econ. Entomol. 58:266-271.
DeDios Lopez-Gonzalez, J., and C. Valenzugla-Calahorro; 1970.  Associated
  decomposition of DDT to DDE in the diffusion of DDT on homoionic clays
  J. Agr. Food Chem. 18:520-523.
Deema, P., E. Thompson and G. W. Ware; 1966.  Metabolism, storage, and
                14
  excretion of C  -endosulfan in the mouse.  J. Econ. Entomol. 59:546-
  550.
Deichmann, W. B. and W. E. MacDonald; 1971.  Organochlorine pesticides
  and human health.  Food Cosmet. Toxicol. 9:91-103. (Chem. Abstr. 75:
  87456y, 1971).
Deichmann, W. B., W. E. MacDonald, E. B. Blum, M. Bevilacqua, J. L. Rad-
  omski, M. L. Keplinger and M. Balkus; 1970.  Tumorogenicity of aldrin,
  dieldrin, and endrin in the albino rat.  Ind. Med. Surg. 39:426-434.
  (Chem. Abstr. 74:75566a, 1971).
Deichmann, W. B., W. E. Macdonald and D. A. Cubit; 1971a.  DDT tissue
  retention:  sudden rise induced by the addition of aldrin to a fixed
  DDT intake.  Science 172:275-276.
Deichmann, W. B., W. E. MacDonald, A. G. Beasley and D. Cubit; 1971b.
  Subnormal reproduction in beagle dogs induced by DDT and aldrin.  Ind.
  Med. Surg. 40:10-20. (Chem. Abstr. 75:97195b, 1971).
Dennis, E. B. and C. A. Edwards; 1964.  Phytotoxicity of insecticides
  and acaricides. IV. Soil applications.  Plant Pathol. 13:173-177.
Derby, S. B. and E. Ruber; 1970.  Primary production:  depression of
  oxygen evolution in algal cultures by organophosphorus insecticides.
  Bull. Environ. Contain.  Toxicol. 5:553-558.
                                  365

-------
Desaiah, D. and R. B. Koch; 1975.  Inhibition of ATPases activity in
  channel catfish brain by kepone and its reduction product.  Bull.
  Environ. Contam. Toxicol. 13:153-158.
Diaz-Mena, D.; 1954.  Phytotoxicity of five insecticides applied to the
  soil during the germination and early growth of four crops.  Acta.
  Agron. (Colombia) 4:175-202. (Chem. Abstr. 49:7173f, 1955).
Dimond, J. B., R. B. Owen, Jr. and A. S. Getchell; 1974.  Distribution
  of DDTR (DDT residue loads) in a uniformly-treated stream.  Bull.
  Environ. Contam. Toxicol. 12:522-528.
Dobson, R. C., J. E. Fahey, D. L. Bailee and E. R. Baugh; 1972.  Dield-
  rin and heptachlor epoxide residues in fat from hogs foraging on corn
  stover in insecticidally treated fields.  Bull. Environ. Contam. Toxi-
  col. 7:311-320.
Dorough, H. W. and B. C. Pass; 1972.  Residues in corn and soils treat-
  ed with technical chlordane and high purity chlordane.  J. Econ. En-
  tomol. 65:976-979.
Dorough, H. W., R. F. Skrentny and B. C. Pass; 1972.  Residues in alfal-
  fa and soils following treatment with technical chlordane and high
  purity chlordane  (HCS 3260) for alfalfa weevil control.  J. Agr. Food
  Chem. 20:42-47.
Dorough, H. W. and R. W. Hemken; 1973.  Chlordane residues in milk and
  fat of cows fed HCS 3260 (high purity chlordane) in the diet.  Bull.
  Environ. Contam. Toxicol. 10:208-216.
Downs, W. G., E. Bordas and L. Navarro; 1951.  Duration of action of
  residual DDT deposits on adobe surfaces.  Science 114:259-262.
Drui, E. G., V. P. Shustova, V. S. Khokhryakova and K. A. Gar; 1971.
  Effect of DDT and the y-isomer of hexachlorocyclohexane on useful soil
  microflora.  Khim. Sel. Khoz. 9:33-35.  (Chem. Abstr. 74:124035n,
  1971).
Duffy, J. R. and N. Wong; 1967.  Residues of organochlorine insecticides
  and their metabolites in soils in the Atlantic provinces of Canada. J.
  Agr. Food Chem. 15:457-464.
                                  366

-------
Dunachie, J. F. and W. W. Fletcher; 1969.  Investigation of the toxi-
  city of insecticides to birds' eggs using the egg injection technique.
  Ann. Appl. Biol. 64:409-423.
Edwards, C. A. and A. R. Thompson; 1973.  Pesticides and the soil fauna.
  Residue Reviews 45:1-80.
Edwards, C. A., A. R. Thompson, K. I. Beynon and M. J. Edwards; 1970.
  Movement of dieldrin through soils.  I. From arable soils into ponds.
  Pestic. Sci. 1:169-173.
Eichelberger, J. W. and J. J. Lichtenberg; 1971.  Persistence of pes-
  ticides in river water.  Environ. Sci. Technol. 5:541-544.
Eisler, R. ; 1970a.  Factors affecting pesticide-induced toxicity in an
  estuarine fish.  Tech. Paper Bur. Sport Fish and Wildlife. #45-46,
  #45, 20 pp.
Eisler, R.; 1970b.  Acute toxicities of organochlorine and organophos-
  phorus insecticides to estuarine fishes.  Tech. Pap. Bur. Sport Fish
  Wlldl. 45-46, #46, 12 pp.
Eldon, M. , I. Dobos and C. J. Krijnen; 1970.  Endosulfan toxicity and
  dietary protein.  Arch. Environ. Health 21:15-19.
Elgar, K. E.; 1966.  Analysis of crops and soils for residues of the
  soil insecticides aldrin and telodrin.  J. Sci. Food Agr. 17:541-545.
Ellis, M. M., B. A. Westfall and M. D. Ellis; 1944.  Toxicity of dichlo-
  rodiphenyl trichloroethane.  Science 100:477.
Eisner, E., D. Bieniek, W. Klein and F. Korte; 1972.  Beitrage zur
                                                                 14
  okologischen Chemie LIT.  Verteilung und Umwandlung von Aldrin-  C,
  Heptachlor-  C und Lindan-  C in der Grunalge Chlorella pyrenoidosa.
  Chemosphere 1:247-250.
Ely, R. E., L. A. Moore, P. E. Hubanks, R. H. Carter and F. W. Poos;
  1953.  Results of feeding methoxychlor-sprayed forage and crystal-
  line methoxychlor to dairy cows.  J. Dairy Sci. 36:309-314.
Engst, R. and M. Kujawa; 1967.  Enzymatischer Abbau des DDT durch
  Schimmelpilze  2. Mitt Reaktionsverlauf des enzymatischen DDT-Abaues.
  Nahrung 11:751-760.
                                  367

-------
Eno, C. F. and P. H. Everett; 1958.  Effects of soil applications of ten
  chlorinated hydrocarbon insecticides on soil microorganisms and the
  growth of stringless black valentine beans.  Soil Sci. Soc. Am.  Proc.
  22:235-238.
Epstein, S. S. and M. S. Legator; 1971.  The Mutagenicity of Pesticides.
  MIT Press, Cambridge, Mass. p. 179.
Epstein, S. S. and H. Shafner; 1968.  Chemical mutagens in the human
  environment.  Nature 219:385-387.
Erben, H. K.; 1972.  Ultrastructure and wall thickness of pathological
  eggshells.  Akad. Wiss. Lit. Mainz Abh. Math-Naturwiss. K16:193-216.
  (Toxline Search).
Eroschenko, V. P. and W. 0. Wilson; 1974.  Photoperiods and age as fac-
  tors modifying the effects of kepone in Japanese quail.  Toxicol.
  Appl. Pharmacol. 29:329-339.
Ettinger, M. B. and D. I. Mount; 1967.  A wild fish should be safe to
  eat.  Environ. Sci. Technol. 1:203-205.
Farmer, W. J., K. Igue, W. F. Spencer and J. P. Martin; 1972.  Volati-
  lity of organochlorine insecticides from soil.  I. Effect of concen-
  tration, temperature, air flow rate, and vapor pressure.  Soil Sci.
  Soc. Am. Proc. 36:443-447.
Farmer, W. J., K. Igue, W. F. Spencer; 1973.  Effect of bulk density on
  the diffusion and volatilization of dieldrin from soil.  J. Environ.
  Qual. 2:107-109.
Farmer, W. J., W. F. Spencer, R. A. Shepherd and M. M. Cliath; 1974.
  Effect of flooding and organic matter applications on DDT residues
  in soil.  J. Environ. Qual. 3:343-346.
Feil, V. J., C. H. Lamoureux and R. G. Zayleskie; 1975.  Metabolism of
  tf.,p'-DDT in chickens.  J. Agr. Food Chem. 23:382-388.
Ferguson, D. E. and C. C. Gilbert; 1967.  Tolerances of three species
  of anuran amphibians to five chlorinated hydrocarbon insecticides.
  J. Miss. Acad. Sci. 13:135-138. (Chem. Abstr. 70:56655e, 1969).
                                  368

-------
Finlayson, D. G. and H. R. McCarthy; 1973.  in:  Environmental Pollu-
  tion by Pesticides, pp. 57-86.  Pesticide residues in plants.  C. A.
  Edwards, ed.; Plenum Press, London, New York.
Fischler, H. M. and F. Korte; 1969.  Sensiblisierte und unsensiblierte
  Photoisomisierung von Cyclodien-Insekticiden.  Tetrahedron Lett.  32:
  2793-2796.
Fisher, N. S.; 1975.  Chlorinated hydrocarbon pollutants and photosyn-
  thesis of marine phytoplankton;  A reassessment.  Science 189:463-
  465.
Fitzhugh, 0. G., A. A. Nelson and M. L. Quaife; 1964.  Chronic oral
  toxicity of aldrin and dieldrin in rats and dogs.  Food Cosmet. Toxi-
  col. 2:551-562.
Fleming, W. E. and W. W. Maines; 1953.  Persistence of DDT in soils of
  the area infested by the Japanese beetle.  J. Econ. Entomol. 46:445-
  449.
Fletcher, D. W. and W. B. Bollen; 1953.  The effects of aldrin on soil
  microorganisms and some of these activities related to soil fertility.
  Appl. Microbiol. 2:349-354.
Focht, D. and M. Alexander; 1971.  Aerobic cometabolism of DDT analogs
  by Hydrogenomonas.  J. Agr. Food Chem. 19:20-22.
Foster, T. S.; 1973.  Evaluation of the possible estrogenic activity of
  methoxychlor in the chicken by means of feeding trials.   Bull.  Environ.
  Contain. Toxicol. 9:234-242.
Foster, T. S.; 1974.  Physiological and biological effects of pesti-
  cide residues in poultry.  Residue Reviews 51:69-121.
Fowkes, F. M., H. A. Benesi, L. B. Ryland, W. M. Sawyer, K. D. Detling,
  E. S. Loeffler, F. B. Folckemer and M. R. Johnson; 1960.  Clay-cata-
  lyzed decomposition of insecticides.  J. Agr. Food Chem. 8:203-210.
Franzke, C., M. Kujawa and R. Engst; 1970.  Enzymatischer Abbau des
  DDT durch Schimmelpilze. 4. Mitt. Einfluss des DDT auf das Wachstum
  von Fusariwn oxysporum sowie auf die Pilzesterase.  Nahrung 14:339-
  346.
                                   369

-------
Fredeen, F. J. H. and R. G. Duffy; 1970.  Insecticide residues in some
  components of the St. Lawrence River ecosystem following applications
  of DDD.  Pestic. Monit. J. 3:219-226.
Fredeen, F. J. H., J. G. Saha and M. H. Balba; 1975.   Residues of meth-
  oxychlor and other chlorinated hydrocarbons in water, sand, and selec-
  ted fauna following injections of methoxychlor black fly larvicide in-
  to the Saskatchewan River, 1972.  Pestic. Monit. J. 8:241-246.
Freed, V. H., R. Haque and D. Schmedding; 1972.  Vaporization and envi-
  ronmental contamination by DDT.  Chemosphere 1:61-66.
Freeman, H. P., A. W. Taylor and W. M. Edwards; 1975.  Heptachlor and
  dieldrin disappearance from a field soil measured by annual residue
  determinations. J. Agr. Food Chem. 23:1101-1105.
Gabliks, J.; 1967.  Insecticidal compounds.  Effects on replication of
  vaccinia and polio virus in human Chang-strain liver cells.  Arch.
  Environ. Health 14:698-702.
Gabliks, J., T. Al-Zubaidy and E. Askari; 1975.  DDT and immunological
  responses.  Arch. Environ. Health 30:81-84.
Gaeb, S., H. Parlar and F. Korte; 1974a.  Beitrage zur bkologischen
  Chemie LXI.  Photoreaktionen des Aldrin/Dieldrin-Metaboliten Dihy-
  drochlordendicarbonsaure(4,5,6,7,8,8-Hexachloro-4,7-Methano-3a,4,7,
  7a-Tetrahydroindan-l,3-Dicarbonsaure).  Tetrahedron 30:1145-1151.
Gaeb, S., H. Parlar, S. Nitz, K. Hustert and F. Korte; 1974b.  Beitrage
  zur okologischen Chemie LXXXI.  Photochemischer Abbau von Aldrin,
  Dieldrin und Photodieldrin als Festkorper im Sauerstoffstrom.  Chemo-
  sphere 3:183-186.
Gaeb, S., H. Parlar, and F. Korte; 1974c.  Beitrage zur 6'kologischen
  Chemie. LXXXII.  Reaktionen von Photodieldrin als Festkorper auf
  Glas und adsorbiert an Kieselgel bei UV-Bestrahlung.  Chemosphere
  3:187-192.
Gaeb, S., W. P. Cochrane, H. Parlar and F. Korte; 1975c.  Photochemische
  Reaktionen von Chlorden-Isomeren des technischen Chlordans.  Z. Natur-
  forsch. 308:239-244.
                                   370

-------
Gaeb, S., S. Nitz, H. Parlar and F. Korte; 1975a.  Beitrage zur okolo-
  gischen Chemie CV.  Photomineralization of certain aromatic xenobio-
  tica as solids in 0_ stream.  Chemosphere 4:251-256.
Gaeb, S., V. Saravanja and F. Korte; 1975b.  Beitrage zur okologischen
  Chemie LXXIII.  Irradiation studies of aldrin and chlordene adsorbed
  on a silica gel surface.  Bull. Environ. Contam. Toxicol. 13:301-306.
Gaines, T. B.; 1969.  Acute toxicity of pesticides.  Toxicol. Appl.
  Pharmacol. 14:515-534.
Gaines, T. B. and R. D. Kimbrough; 1970.  Oral toxicity of mirex in adult
  and suckling rats.  Arch. Environ. Health 21:7-14.
Gannon, N. and J. H. Bigger; 1958.  Conversion of aldrin and heptachlor
  to their epoxides in soil.  J. Econ. Entomol. 51:1-2.
Gannon, N. and G. C. Decker; 1958.  The conversion of aldrin to dieldrin
  on plants.  J. Econ. Entomol. 51:8-11.
Gannon, N. and G. C. Decker; 1960.  The excretion of dieldrin, DDT, and
  heptachlor epoxide in milk of dairy cows fed on pastures treated with
  dieldrin, DDT, and heptachlor.  J. Econ. Entomol. 53:411-415.
Gawaad, A. A. A., M. A. Hamad and F. H. El-Gayar; 1971.  Effect of the
  canal irrigation system used in the UAR on the persistence of soil
  insecticide.  Int. Pest. Contr. 13(4):8-10.  (Chem. Abstr. 76:42720j,
  1972).
Gawaad, A. A. A., M. H. Hamad and F. H. El-Gayar; 1972a.  Soil insecti-
  cides.  X.Effect of soil insecticides on soil microorganisms.  Zentralbl,
  Bakteriol., Parasitenk., Infektionskr. Hyg., Abt. 2; 127:290-295.
Gawaad, A. A. A., M. Hamad and F. H. El-Gayar; 1972b.  Soil insecti-
  cides.  XI. Effect of soil insecticides on the nitrogen transformation
  of treated soils.  Zentralbl. Bakteriol., Parasitenk., Infektionskr.
  Hyg., Abt. 2; 127:296-300.
Gawaad, A. A. A., A. 11. El-Minshawy and M. Zein; 1973a.  Effect of some
  soil insecticides on nodule-forming bacteria of the broad bean and
  Egyptian clover.  Agrokem. Talajtan 22:153-160. (Chem. Abstr. 79:
  143387y, 1973).
                                   371

-------
Gawaad, A. A. A., M. Hamad and F. H. El-Gayar; 1973b.  Effects of some
  soil insecticides on the transformation of nitrogen in soils.  Agro-
  kern. Talajtan 22:169-174. (Chem. Abstr. 80:779n, 1974).
Gawaad, A. A. A., M. Hamad and F. H. El-Gayar; 1973c.  Effect of some
  soil insecticides on soil microorganisms.   Agrokem. Talajtan 22:161-
  168.
Gellert, R.,  W. L. Heinrichs,  W.  Leroy and R. S. Swerdloff; 1972.  DDT
  homologs.  Estrogen-like effects on the vagina, uterus, and pituitary
  of the rat.  Endocrinology 91:1095-1100.
Gellert, R.,  W. L. Heinrichs and R. Swerdloff; 1974.  Effects of neona-
  tally-administered DDT homologs on reproductive function in male and
  female rats.  Neuroendocrinology.  16:84-94.
Gibson, J. R., G. W. Ivie and H.  W. Dorough; 1972.  Fate of mirex and
  its major photodecomposition product in rats.  J. Agr. Food Chem. 20:
  1246-1248.
Gillett, J. W., T. M. Chan and L. C. Terriere; 1966.  Interactions be-
  tween DDT analogs and microsomal epoxidase systems.  J. Agr. Food Chem.
  14:540-545.
Ginsburg, J.  M.; 1953.  Rate of decomposition of the newer insecticides
  when exposed outdoors to direct sunlight.   Proc. N. J. Mosquito Ex-
  term. Assoc. 40:163-168. (Chem. Abstr. 48:2307i, 1954).
Gish, C. D.;  1970.  Organochlorine insecticide residues in soils and
  soil invertebrates from agricultural lands.  Pestic. Monit. J. 3:241-
  252.
Glancey, B. M., W. Roberts and J. Spence; 1970.  Effect on honeybee pop-
  ulations of exposure to bait containing mirex for control of imported
  fire ants.   Amer. Bee  J. 110:314. (Chem.  Abstr. 73:97765w, 1970).
Goerlitz, D.  F. and L. M. Law; 1974.  Distribution of chlorinated hydro-
  carbons in stream-bottom material.  J. Res. U.S. Geol. Surv. 2:541-
  543.
Goldsworthy,  M. C. and A. C. Foster; 1950.  Effect of organic sprays on
  orchard soils.  Am. Fruit Grower 70:52-53.
                                   372

-------
Good, E. E. and G. W. Ware; 1969.  Effects of insecticides on reproduc-
  tion in the laboratory mouse. IV. Endrin and dieldrin.  Toxicol. Appl.
  Pharmacol. 14:201-203.
Good, E. E., G. W. Ware and D. F. Miller; 1965.  Effects of insecti-
  cides on reproduction in the laboratory mouse: I. Kepone.  J. Econ.
  Entomol. 58:754-757.
Gorbach, S. and W. Knauf; 1971.  Endosulfan and the environment.  The
  behavior of endosulfan residues in water and its effect on water or-
  ganisms.  Schriftner. Ver. Wasser-, Boden-, Lufthyg., Berlin-Dahlem
  No. 34, 85-93.  (Chem. Abstr. 75:97538r, 1971).
Gorbach, S. G., 0. Crist, H. M. Kellner, G. Kloss and E. Boerner; 1968.
  Metabolism of endosulfan in milk sheep.  J. Agr. Food Chem. 16:950-
  953.
Gorbach, S., R. Haarring, W. Knauf and H. J. Werner; 1971.  Residue an-
  alysis and biotests in rice fields of East Java with Thiodan.  Bull.
  Environ. Contain. Toxicol. 6:193-199.
Gordienko, E. I.; 1964.  Effect of hexachlorocyclohexane (BHC) and hep-
  tachlor on soil fertility.  Rol Udobrenii I Drugikh Faktorov V Povy-
  shenii Produktivn. Rast. Sb. 1964:186-191. (Chem. Abstr. 63:18964b,
  1965).
Grandolfo, N., I. Camoni, I. DiSimone, V. Leonie, G. Ramelli and A.
  Sampaolo; 1967.  Persistence of parathion, methylparathion, malathion,
  carbaryl, DDT, and Kelthane residues in lettuce.  Ann. Fac. Agr.,
  Univ. Catt. Sacro. Cuore. 7:357-376. (Chem. Abstr. 70:46232a, 1969).
Green, V. A.; 1970.  in:  Trace Subst. Environ. Health-3.  Effects of
  pesticides on rat and chick embryos.  Proc. Univ. Mo. Annu. Conf.,
  3rd, 1969:183-209. (Chem. Abstr. 73:130169e, 1970).
Greer, D. E., J. E. Keil, L. W. Stillway, and S. H. Sandifer; 1974.
  Effect of DDT and PCB (polychlorinated biphenyl) on lipid metabolism
  in Esaher-iohia aoli and BaGteroides fragilis.  Bull. Environ. Contain.
  Toxicol. 12:295-300.
                                  373

-------
 Gregory, W. W., Jr., J. K. Reed and L. E. Priester; 1969.  Accumulation
  of parathion and DDT by some algae and protozoa.  J. Protozool. 16:69-
  71.
Greim, H.; 1970.  Toxicity and therapeutic utility of DDT and its meta-
  bolites.  Aerztl. Forsch. 24:197-201. (Chem. Abstr. 73:54954q, 1970).
Greve, P. A. and H. G. Verschuuren; 1971.   Toxicity of Endosulfan for
  fish in surface waters.  Schriftenr. Ver. Wasser-, Boden-, Lufthyg.,
  Berlin-Dahlem No. 34, 63-67. (Chem. Abstr. 75:109150y, 1971).
Greve, P. A. and S. L. Wit; 1971a.  Endosulfan in the Rhine River.  J.
  Water Pollut. Contr. Fed. 43:2338-2348.  (Chem. Abstr. 76:37157b, 1972).
Greve, P. A. and S. L. Wit; 1971b.  Endosulfan in Rijnwater.  Chem.
  Weekbl. 67:7-9.
Grolleau, G. and Y. Froux; 1973.  Effet de 1'heptachlore sur la repro-
  duction de la caille Coturnix ootwcnix Japoniaa.  Ann. Zool.-Ecol.
  Anim. 5:261-270.
Grosch, D. S.; 1967.  Poisoning with DDT:   Effect on reproductive per-
  formance of Artemia.  Science 155:592-593.
Grosch, D. S. and L. R. Valcovic; 1967.  Chlorinated hydrocarbon insec-
  ticides are not mutagenic in Bracon hebeter tests.  J. Econ. Entomol.
  60:1177-1179.
Grossmann, F. and D. Steckhan; 1960.  Nebenwirkungen einiger Insektizide
  auf pathogene Bodenpilze.  Z. Pflanzenkrankh. U. Pflanzenschutz 67:7-
  19.
Guenzi, W. D. and W. E. Beard; 1967.  Anaerobic biodegradation of DDT to
  DDD in soil.  Science 156:1116-1117.
Guenzi, W. D. and W. E. Beard; 1968.  Anaerobic conversion of DDT to
  DDD and aerobic stability of DDT in soil.  Soil. Sci. Soc. Amer.,
  Proc. 32:522-524.
Guenzi, W. D. and W. E. Beard; 1970.  Volatilization of lindane and DDT
  from soils.  Soil Sci. Soc. Amer., Proc. 34:443-447.
Gul'ko, A. G.; 1968.  Toxicology of the acaricide Kelthane.  Gig. Tok-
  sikol. Pestits, Klin. Otravleni. No. 4,  113-117. (Chem. Abstr. 69:
  34315w, 1968).
                                  374

-------
Gunther, F. A., D. L. Lindgren and M. I. Elliot; 1946.  Persistence of
  certain DDT deposits under field conditions.  J. Econ. Entomol. 39:
  624-627.
Gunther, F. A. and L. R. Tow; 1946.  Inhibition of the catalyzed ther-
  mal decomposition of DDT.  Science 104:203-204.
Gunther, F. A., H. P. Hermanson, L. D. Anderson and M. J. Garber; 1971.
  Installment application effects upon insecticide residue content of
  a California soil.  J. Agr. Food Chem. 19:722-726.
Guyer, G. E., P. L. Adkisson, K. DuBois, C. Menzie, H. P. Nicholson, G.
  Zweig and C. L. Dunn; 1971.  Toxaphene Status Report:  Environmental
  Protection Agency, Washington, D. C.
Haag, H. B., J. K. Finnegan, P. S. Larson, W. Riese and M. L. Dreyfuss;
  1950.  Comparative chronic toxicities for warm-blooded animals of
  2,2-bis-(n-chlorophenyl)-l,l,l-trichloroethane (DDT) and 2,2-bis€
  @?-methoxyphenyl)-l,l,l-trichloroethane  (DMDT, methoxychlor).  Arch.
  Intern. Pharmacodynamie 83:491-504. (Chem. Abstr. 45:4340e, 1951).
Haegele, M. A. and R. K. Tucker; 1974.  Effects of 15 common environ-
  mental pollutants on eggshell thickness in mallards and coturnix.
  Bull. Environ. Contam. Toxicol. 11:98-102.
Halvorson, H., M. Ishaque, J. Solomon, and 0. W. Grussendorf; 1971.
  Biodegradability test for insecticides.  Can. J. Microbiol. 17:585-
  591.
Hannon, M. R., Y. A. Greichus, R. L. Applegate and A. C. Fox; 1970.  Eco-
  logical distribution of pesticides in Lake Poinsett, South Dakota.
  Trans. Amer. Fish Soc. 99:496-500.
Harris, C. I.; 1969.  Movement of pesticides in soil.  J. Agr. Food
  Chem. 17:80-82.
Harris, C. R.; 1964.  Influence of soil moisture on the toxicity of
  insecticides in a mineral soil to insects.  J. Econ. Entomol. 57:
  946-950.
Harris, C. R.; 1967.  Further studies on the influence of soil moisture
  on the toxicity of insecticides in soil.  J. Econ. Entomol. 60:41-47.
                                   375

-------
Harris, C. R.; 1972a.  Behavior of dieldrin in soil.  Laboratory studies
  on the factors influencing biological activity.  J. Econ. Entomol.
  65:8-13.
Harris, C. R.; 1972b.  Factors influencing the biological activity of
  technical chlordane and some related components in the soil.  J. Econ.
  Entomol. 65:341-347.
Harris, C. R.; 1973.  Behavior and persistence of biological activity of
  HCS 3260 (AG-chlordan) in soil under laboratory conditions.  Proc,,
  Entomol. Soc. Ont. 1972, 103:10-16.
Harris, C. R. and W. W. Sans; 1967.  Absorption of organochlorine in-
  secticide residues from agricultural soils by root crops.  J. Agr.
  Food Chem.  15:861-863.
Harris, C. R. and W. W. Sans; 1969a.  Vertical distribution of residues
  of organochlorine insecticides in soils collected from six farms in
  southwestern Ontario.  Proc. Entomol. Soc. Ont. 100:156-164. (Chem.
  Abstr. 74:86789b, 1971).
Harris, C. R. and W. W. Sans; 1969b.  Pesticides in soil.  Absorption of
  organochlorine insecticide residues from agricultural soils by crops
  used for animal feed.  Pestic. Monit. J. 3:182-185.
Harris, C. R. and W. W. Sans; 1971.  Insecticide residues in soils on
  16 farms in southwestern Ontario-1964, 1966, and 1969.  Pestic.
  Monit. J. 5:259-267.
Harris, C. R. and W. W. Sans; 1972a.  Behavior of dieldrin in soil:
  Microplot field studies on the influence of soil type on biological
  activity and absorption by carrots.  J. Econ. Entomol. 65:333-335.
Harris, C. R. and W. W. Sans; 1972b.  Behavior of heptachlor epoxide
  in soil.  J. Econ. Entomol. 65:336-341.
Harris, C. R., W. W. Sans and J. R. W. Miles; 1966.  Exploratory studies
  on occurrence of organochlorine insecticide residues in agricultural
  soils in southwestern Ontario.  J. Agr. Food Chem. 14:398-403.
Harris, S. J., H. C. Cecil and J. Bitman; 1974.  Effect of several
  dietary levels of technical methoxychlor on reproduction in rats.
  J. Agr.  Food Chem.   22:969-973.
                                   376

-------
Hartley, G. S.; 1968.  Evaporation of pesticides.  Adv. Chem. Series
  86:115-134.
Hathaway, D. E., J. A. Moss, J. A. Rose and D. J. M. Williams; 1967.
  Transport of dieldrin from mother to blastocyst and from mother to
  fetus in pregnant rabbits.   Eur. J. Pharmacol. 1:167-175.
Head, W. K. and R. B. McKercher; 1971.  Recovery of pesticide residues
  from chernozemic soils.  Can. J. Soil Sci. 51:423-430.
Heinisch, E.; 1973.  The contamination of the soil with agrochemicals
  and side effects deriving from it.  Wiss. Z. Tech. Univ. Dresden
  22:670-674. (Toxline Data Base).
Herzel, F.; 1972.  Organochlorine insecticides in surface waters in
  Germany.  Pestic. Monit. J. 6:179-187.
Hill, D. W. and P. L. McCarty; 1967.  Anaerobic degradation of selected
  chlorinated hydrocarbon pesticides.  J. Water Pollut. Contr. Fed. 39:
  1259-1277.
Hiltibran, R. C.; 1974.  Oxygen and phosphate metabolism of bluegill
  liver mitochondria in the presence of some insecticides.  Trans. 111.
  State Acad. Sci. 67(2):228-237.
Hodge, H. C., A. M. Boyce, W. B. Deichmann and H. F. Kraybill; 1967.
  Toxicology and no-effect levels of aldrin and dieldrin.  Toxicol.
  Appl. Pharmacol. 10:613-675.
Hodge, H. C., E. A. Maynard, W. L. Downs, J. K. Ashton9 and L. J.
  Salerno; 1966.  Tests on mice for evaluating carcinogenicity.  Toxi-
  col. Appl. Pharmacol. 9:583-596.
Hodkinson, M. and S. A. Dalton; 1973.  Interactions between DDT and riv-
  er fungi.  II. Influence of culture conditions on the compatibility
  of fungi and  p^p^-DDT.  Bull. Environ. Contam. Toxicol. 10:356-359.
Holmstead, R. L., S. Khalifa and J. E. Casida; 1974.  Toxaphene compo-
  sition analysed by combined gas chromatography-chemical ionization
  mass spectrometry.  J. Agr. Food Chem. 22:939-944.
Homonnay-Csehi, E.; 1971.  Biological determination of aldrin residues
  in the soil after application of superphosphate with aldrin.  Kiser-
                                  377

-------
  letugyi Kozlem., A 1969; 62:185-193. (Chem. Abstr. 76:82139h, 1972).
Hrdina, P. D., R. L. Singhal and G. M. Ling; 1975.  DDT and related
  chlorinated hydrocarbon insecticides.  Pharmacological basis of
  their toxicity in mammals.  Adv. Pharmacol. Chemother. 12:31-88.
Huang, J. C.; 1971.  Effect of selected factors on pesticide sorption
  and desorption in the aquatic system.  J.  Water Pollut. Contr. Fed.
  43:1739-1748. (Chem. Abstr. 75:97551q,  1971).
Huber, J. J.; 1965.  Some physiological effects of the insecticide
  Kepone in the laboratory mouse.  Toxicol.  Appl. Pharmacol. 7:516-524.
Hughes, R. A. and G. F. Lee; 1973.  Toxaphene accumulation in fish in
  lakes treated for rough fish control.  Environ. Sci. Technol. 7:934-
  939.
Hurst, J. G., W. S. Newcomer and J. A. Morrison; 1974.  Effects of DDT,
  toxaphene, and polychlorinated biphenyl on thyroid function in bob-
  white quail.  Poult. Sci. 53:125-133.
Igue, K., W. J. Farmer, W. F. Spencer and J. P. Martin; 1972.  Volati-
  lity of organochlorine insecticides from soil: II. Effects of rela-
  tive humidity and soil water content on dieldrin volatility.  Soil
  Sci. Soc. Amer., Proc. 36:447-450.
Ivie, G. W.; 1973.  Nature and toxicity of two oxychlordane photoisomers.
  J. Agr. Food Chem. 21:1113-1115.
Ivie, G. W. and J. E. Casida; 1971.  Sensitized photodecomposition and
  photosensitizer activity of pesticide chemicals exposed to sunlight
  on silica gel chromatoplates.  J. Agr.  Food Chem. 19:405-409.
Ivie, G. W., J. R. Knox, S. Khalifa, I. Yamamoto and J. E. Casida; 1972.
  Novel photoproducts of heptachlor epoxide, trans-chlordane, and trans-
  nonachlor.  Bull. Environ. Contain. Toxicol. 7:376-382.
Ivie, G. W., H. W. Borough and E. G. Alley;  1974.  Photodecomposition
  of mirex on silica gel chromatoplates exposed to natural and artifi-
  cial light.  J. Agr. Food Chem. 22:933-935.
lyengar, L. and A. Rau; 1973.  Metabolism of chlordan and heptachlor by
  Aspergillus niger.  J. Gen. Appl. Microbiol. 19:321-324.
                                   378

-------
Jackson, C. , Jr., I. L. Lindahl, P. Reynolds and G. M. Sidwell; 1975.
  Effects of methoxychlor and malathion on semen characteristics of
  rams.  J. Anim. Sci. 40:514-517.
Jager, K. W.; 1970.  Aldrin, Dieldrin,, Endrin and Telodrin.  Elsevier,
  Amsterdam.
Jager, K. W.; 1971.  Epidemiological and toxological study covering 15
  years in workers occupationally exposed to aldrin and dieldrin. Meded.
  Fac. Landbouwwetensch., Rijksuniv. Gent 36:1114-1118. (Chem. Abstr.
  77:44029k, 1972).
Joensson, A. and G. Faraeus; 1960.  Effect of aldrin on soil bacteria.
  KGL. Lantbrukshoegskol. Ann. 26:323-332. (Chem. Abstr. 55:14793a,
  1961).
Johansen, C. A. and M. G. Kleinschmidt; 1972.  Insecticide formulations
  and their toxicity to honeybees.  J. Apicult. Res. 11:59-62.
Johnson, B. T. and J. 0. Kennedy; 1973.  Biomagnification of p3p '-DDT
  and methoxychlor by bacteria.  Appl. Microbiol. 26:66-71.
Johnson, L. G. and R. L. Morris; 1971.  Chlorinated hydrocarbon  pesti-
  cides in Iowa rivers.  Pestic. Monit. J. 4:216-219.
Johnson, T. B., H. 0. Saunders and R. S. Campbell; 1971.  Biological
  magnification and degradation of DDT and aldrin by freshwater inver-
  tebrates.  J. Fish Res. Bd. Can. 28:705-709.
Johnson, W. D., G. F. Lee and D. Spyrioakis; 1966.  Persistence of tox-
  aphene in treated lakes.  Air Water Pollution 10:555-560.
Johnston, W. R., F. T. Ittihadieth, K. R. Craig and A. F. Pillsbury; 1967.
  Insecticides in tile drainage effluent.  Water Resour. Res. 3:525-537.
Johnston, H. R., V. K. Smith and H. R. Seal; 1971.  Chemicals for sub-
  terranean termite control.  Results of long-term tests.  J. Econ.
  Entomol. 64:745-748.
Jones, L. W.; 1952.  Stability of DDT and its effect on microbial acti-
  vities of soil.  Soil Sci. 73:237-241.
Jones, L. W. ; 1956.  Effects of some pesticides on microbial activities
  of the soil.  Utah State Agr. Coll., Agr. Expt. Sta. Bull. #390, 17 pp.
                                    379

-------
  (Chem. Abstr. 51:9071g, 1957).
Jones, K. H., D. M. Sanderson and D. N. Noakes; 1968.  Acute toxicity
  data for pesticides.  World Rev. Pest Contr. 7:135-143.
Ju-Chang, H. and C-S Liao; 1970.  Adsorption of pesticides by clay min-
  erals.  J. Sanit. Eng. Div., Amer. Soc. Civil Eng. 96:1057-1078.
  (Chem. Abstr. 74:63461z, 1971).
Jukes, T. H.; 1970.  DDT and tumors in experimental animals.  Int. J.
  Environ. Stud. 1:43-46.
Kagan, Y. S., S. I. Fudel-Osipova, B. I. Khaikina, U. A. Kuz'Minskaya
  and S. D. Koton; 1969.  Harmful effect of DDT and its mechanism of
  action.  Residue Reviews 27:43-79.
Kagan, Y. S., A. M. Lukaneva and G. A. Rodionov; 1974.  Effect of pes-
  ticides on the development of some kinds of experimental pathology of
  the vascular system.  Farmakol. Toksikol. 9:189-196. (Chem. Abstr.
  82:11958n, 1975).
Kaneda, Y., K. Nakamura, H. Nakahara and M. Iwaida; 1974.  Degradation
  of organochlorine pesticides with calcium hypochlorite.  I.  Eisei
  Kagaku 20:296-299.  (Chem. Abstr. 82:94190e, 1975).
Kapoor, I. P., R. L. Metcalf, A. S. Hirwe, P-Y Lu, J. R. Coats and R. F.
  Nystrom; 1972.  Comparative metabolism of DDT, methylchlor, and eth-
  oxychlor in mouse, insects, and in a model ecosystem.  J. Agr. Food
  Chem. 20:1-6, 1972.
Kapoor, I. P., R. L. Metcalf, R. F. Nystrom and G. K. Sangha; 1970.
  Comparative metabolism of methoxychlor, methiochlor, and DDT in
  mouse, insects, and in a model ecosystem.  J. Agr. Food Chem. 18:
  1145-1152.
Kaul, R., D. Bieniek and W. Klein; 1972.  Beitrage zur okologischen
  Chemie XLVI.  Isolierung und Indentifizierung von Metaboliten des
    C-ferans-Chlordans aus Weisskohl.  Chemosphere 1:139-142.
Kawano, Y., A. Bevenue and H. Beckman and F. Erro; 1969.  Studies on
  the effect of sulfuric-forming nitric acid treatment on the analyti-
  cal character of toxaphene.  Ass. Offic. Anal. Chem. J., 52:167-172.
                                  380

-------
Kearney, P. C., E. A. Woolson, J. R. Plimmer and A. R. Isensee; 1969.
  Decontamination of pesticides in soils.  Residue Reviews 29:137-149.
Kemeny, T. and R. Tarian; 1966.  Investigations on the effect of chron-
  ically administered small amounts of DDT in mice.  Experientia 22:
  748-749.
Kennedy, G. L., Jr., J. P. Frawley and J. C. Calandra; 1973.  Multi-
  generation reproductive effects of three pesticides in rats.  Toxicol.
  Appl. Pharmacol. 25:589-596.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1969.  Chemi-
  cal and thermal methods for disposal of pesticides.  Residue Reviews
  29:89-104.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman; 1972a.  Chemical and
  thermal aspects of pesticide disposal.  J. Environ. Qual. 1:63-65.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1972b.  Analy-
  sis of decomposition products of pesticides.  J. Agr. Food Chem. 20:
  341-343.
Keplinger, M. L. and W. B. Deichman; 1967.  Acute toxicity of combina-
  tions of pesticides.  Toxicol. Appl. Pharmacol. 10:586-595.
Khaikina, B. I. and V. F. Shilina; 1971.  Effect of some organochlorine
  pesticides on serotonin metabolism.  Farmakol. Toksikol. (Moscow) 34:
  357-359. (Chem. Abstr. 75:62531f, 1971).
Khalidov, A. B., F. G. Gatilova, and S. M. Samosova; 1968.  Effect of
  insecticides on the soil layer of the biocenosis of a beet field.
  Mater. Faune. Ekol. Pochvoobitayushchikh Bespozvonochnykh 1968:141-
  161.  (Chem. Abstr. 71:90216t, 1969).
Khalifa, S., T. R. Mon, J. L. Engel and J. E. Casida; 1974.  Isolation
  of 2,2,5-endOj6-exo38,9,10-heptachlorbornane and an octachloro toxi-
  cant from technical toxaphene.  J. Agr. Food Chem. 22:653-657.
Khan, M. A. Q., R. H. Stanton, D. J. Sutherland, J. D. Rosen and N.
  Maitra; 1973.  Toxicity-metabolism relation of the photoisomers of
  certain chlorinated cyclodiene insecticide chemicals.  Arch. Environ.
  Contam. Toxicol. 1:159-169.
                                  381

-------
Kiigemagi, U. and L. C. Terriere; 1972.  Persistence of DDT in orchard
  soils.  Bull. Environ. Contain. Toxicol. 7:348-352.
Kiigemagi, U., H. E. Morrison, J. E. Roberts and W. B. Bollen; 1958.
  Biological and chemical studies on the decline of soil insecticides.
  J. Econ. Entomol. 51:198-204.
Kimbrough, R. , T. B. Gaines and J. D. Sherman; 1964.  Nutritional fac-
  tors, long-term DDT intake, and chloro-leukemia in rats.  J. Nat.
  Cancer Inst. 33:215-216.
King, R. L., N. A. Clark and R. W. Hemken; 1966.  Distribution, move-
  ment, and persistence of heptachlor and its epoxide in alfalfa plants
  and soil.  J. Agr. Food Chem. 14:62-65.
Kiss, L.; 1967.  Laboratory investigation of the effect of various in-
  secticides on the most important mycorrhiza fungi associated with
  pines.  Erdeszeti Kut. 63:241-247. (Chem. Abstr. 68:58692x, 1968).
Klein, A. K. and J. D. Link; 1967.  Field weathering of toxaphene and
  chlordane.  J. Assoc. Off. Anal. Chem. 50:586-591.
Klein, W., S. Zarif and I. Weisgerber;  1972.  Ecological Chemistry.
                                       14
  XXXVI.  Residual behavior of isodrin-  C and its conversion products
  in white cabbage and carrots.  Chem.  Mikrobiol. Technol. Lebensm. 1:
  121-125. (Chem. Abstr. 78:24921n, 1973).
Klein, W., J. Kohli, II Weisgerber and F. Korte; 1973.  Fate of aldrin-£
  14
    C in potatoes and soil under outdoor conditions.  J. Agr. Food Chem.
  21:152-156.
Klevay, L. M.; 1970.  Dieldrin excretion by the isolated perfused rat
  liver.  A sexual difference.  Toxicol. Appl. Pharmacol. 17:813-815.
Knauf, W. and E. F. Schulze; 1973.  Toxicity of endosulfan and its
  metabolites to aquatic organisms.  Meded. Fac. Landbouwwetensch.,
  Rijksuniv. Gent 38:717-732.  (Chem. Abstr. 81:34185e, 1974).
Knoevenagel, K. and R. Himmelreich; 1973.  Photolysis of Kepone and
  Kelevan.  Z. Pflanzenkr. Pflanzenschutz. 80:155-159. (Chem. Abstr.
  80:70044t, 1974).
Knox, J. R., S. Khalifa, G. W. Ivie, and J. E. Casida; 1973.  Charac-
                                  382

-------
  terization of the photoisomers from eis- and trans-chlordanes, trans-
  nonachlor, and heptachlor epoxide.  Tetrahedron 20:3869-3879.
Knutson, H., A. M. Kadoum, T. L. Hopkins, G. F. Swoyer and T. L. Har-
  vey; 1971.  Insecticide usage and residues in a newly developed Great
  Plains irrigation district.  Pestic. Monit. J. 5:17-27.
Ko, W. H. and J. L. Lockwood; 1968a.  Conversion of DDT to ODD in soil
  and the effect of these compounds on soil microorganisms.  Can. J.
  Microbiol. 14:1069-1073.
Ko, W. H. and J. L. Lockwood, 1968b.  Accumulation and concentration of
  chlorinated hydrocarbon pesticides by microorganisms in soil.  Can. J.
  Microbiol. 14:1075-1078.
Kohli, J., I. Weisgerber and W. Klein; 1973a.  Beitrage zur okologischen
                                          14
  Chemie LVIII.  Zum Transport von Aldrin-  C und Umwandlungsprodukten
  im Boden.  Chemosphere 2:125-130.
Kohli, J., I. Weisgerber, W. Klein and F. Korte; 1973b.  Beitrage zur
  b'kologischen Chemie LIX.  Riickstandsverhalten und Umwandlung von
           14
  Dieldrin-  C in Kulturpflanzen, Boden und Sickerwasser nach Boden-
  applikation.   Chemosphere 2:153-156.
Kokke, R.; 1970a.  Pesticide and herbicide interaction with microbial
  ecosystems.  Antonie van Leeuvenhoek; J. Microbiol. Serol. 36:580-
  581.
Kokke, R.; 1970b.  DDT; its action and degradation in bacterial popu-
  lations.  Nature 226:977-978.
Kolipinski, M. C., A. L. Higer and M. L. Yates; 1971.  Organochlorine
  insecticide residues in Everglades National Park and Loxahatchie
  Wildlife Refuge, Florida.  Pestic. Monit. J. 5:281-288.
Konar, S. K.; 1970.  Toxicity of heptachlor to aquatic life.  J. Water
  Pollut. Contr. Fed. 42(8)(Pt2), R299-R303.
Korschgen, L. J.; 1971.  Disappearance and persistence of aldrin after
  five annual applications.  J. Wildl. Manage. 35:494-500.
Korte, F. and H. Arent; 1965.  Metabolism of insecticides IX. Isolation
  and identification of dieldrin metabolites from urine of rabbits
                                  383

-------
                                        14
  after oral administration of dieldrin-  C.  Life Sci. 4:2017-
  2026.
Korte, F., W. Klein, I. Weisgerber, R. Kaul, W. Mueller and A. Djirsarai;
  1970.  in:  Pestic. Symp.; Collect Pap.  Inter. Amer. Conf. Toxicol.
  Occup. Med.3 6th, ?th3 1968-1970.  pp. 51-60.  W. B. Deichmann, ed.
  Halos Ass., Inc., Miami.  Recent results in studies on the fate of
  chlorinated insecticides.
Koula, J.; 1970.  Absorption of allicyclic chlorinated insecticides in
  their solid forms and their retention in plants in relation to var-
  ious soil types.  Pol'nohospodarstvo 16:214-220. (Chem. Abstr. 73:
  108698e, 1970).
Kralovic, J.; 1974.  Inhibitory effect of toxaphene on the photosynthe-
  sis of alfalfa.  Pol'nohospodarstvo 20:745-754. (Chem. Abstr. 83:1824x,
  1975).
Krasovskii, G. N. and S. A. Shigan; 1970.   Assessment of the mechanism
  of the cumulative action of toxic substances.  Gig. Sanit. 35:17-21.
  (Chem. Abstr. 73:760743, 1970).
Krechniak, J., R. Dubrawski and W. Czarnowski; 1973.  Residues of DDT
  in soils of the Koscierzyna district.  Rozpr. Wydz. 3:  Nauk Mat-
  Przyr., Gdansk. Tow. Nauk. 8:65-71. (Chem. Abstr. 82:52591f, 1975).
Kricher, J. C. , J. C. Urey, and M. L. Hawes; 1975.  The effects of
  mirex and methoxychlor on the growth and productivity of Chlovella
  pyreno-idosa.  Bull. Environ. Contain. Toxicol. 14:617.
Ruhr, R. J., A. C. Davis and J. B. Bourke; 1974.  DDT residues in soil,
  water, and fauna from New York apple orchards.  Pestic. Monit. J. 7:
  200-204.
Ruhr, R. J., A. C. Davis and E. F. Taschenberg; 1972.  DDT residues in
  a vineyard soil after 24 years of exposure.  Bull. Environ. Contain.
  Toxicol. 8:329-333.
Kunze, F. M., E. P. Laug and C. S. Prickett; 1950.  The storage of meth-
  oxychlor in the fat of the rat.  Proc. Soc. Exptl. Biol. Med. 75:415-
  416.
                                   384

-------
Kuz'minskaya, U. A. and V. E. Yakushko; 1970.  Effect of DDT and Sevin
  on the activity of some liver enzymes.  Gig. Sanit. 35:97-99. (Chem.
  Abstr. 73:76076g, 1970).
LaFleur, K. S.; 1974.  Toxaphene-soil-solvent interactions.  Soil Sci.
  117:205-210.
LaFleur, K. S., G. A. Wojeck and W. R. McCaskill; 1972.  Movement of
  toxaphene and fluometron through Dunbar soils to underlying ground
  water.  J. Environ. Qual. 2:515-518.
Lakota, S.; 1974.  Toxic action of methoxychlor on certain water ani-
  mals.  Tagungsber., Akad. Landwirtschaftswiss. D.D.R. 126:111-115.
  (Chem. Abstr. 83:73043q, 1975).
Lange, B. and G. Crueger; 1960.  Proa. Intern. Congr. Crop Protect.,
  4th Congr.  Hamburg, 1957; 2:1349-1355.  Controlling field mice by
  surface treatments.  (Chem. Abstr. 55:8744f, 1961).
Langlois, B. E.; 1967.  Reductive dechlorination of DDT by Esoheriohia
  ooli.  J. Dairy Sci. 50:1168-1170.
Laubscher, J. A., G. R. Dutt and C. C. Roan; 1971.  Chlorinated insec-
  ticide residues in wildlife and soil as a function of distance from
  application.  Pestic. Monit. J. 251-258.
Lauer, G. J., H. P. Nicholson, W. S. Cox and J. I. Teasley; 1966.
  Pesticide contamination of surface waters by sugar cane farming in
  Louisiana.  Trans. Am.  Fisheries Soc. 95:310-316.
Lay, J. P., I. Weisgerber and W. Klein; 1975.  Conversion of the aldrin/
                                                         14
  dieldrin metabolite dihydrochlordene dicarboxylic acid-  C in rats.
  Pestic. Biochem. Physiol. 5:226-232.
Lee, G. K., F. D. Friedrich, B. C. Post and H. Whaley; 1971.  Thermal
  destruction of DDT-bearing powders.  Can. Mines Br., Res. Rep. R234,
  13 pp.
Leigh, G. M.; 1969.  Degradation of selected chlorinated hydrocarbon
  insecticides.  J. Water Pollut. Contr. Fed. 4l:R450-R460.
Leland, H. V., W. N. Bruce and N. F. Shimp; 1973.  Chlorinated hydro-
  carbon insecticides in sediments of southern Lake Michigan.  Environ.
                                  385

-------
  Sci. Technol. 7:833-838.
Lemire, R. and V. Fredette; 1961.  Action of DDT on bacteria.  Rev. Can.
  Biol. 20:833-836. (Chem. Abstr. 56:12081k, 1962).
Leshniowsky, W. 0., P. R. Dugan, R. M. Pfister, J. I. Frea, and C. I.
  Randies; 1970.  Aldrin removal from lake water by flocculent bacteria.
  Science 169:993-995.
Li, C. F. and R. L. Bradley, Jr.; 1969.  Degradation of chlorinated
  hydrocarbon pesticides in milk and butteroil by ultraviolet energy.
  J. Dairy Sci. 52:27-30.
Lichtenstein, E. P.; 1958.  Movement of insecticides in soils under
  leaching and non-leaching conditions.  J. Econ. Entomol. 51:380-383.
Lichtenstein, E. P.; 1959.  Absorption of some chlorinated hydrocarbon
  insecticides from soils into various crops.  J. Agr. Food Chem. 7:
  430-433.
Lichtenstein, E. P. and J. B. Polivka; 1959.  Persistence of some chlor-
  inated hydrocarbon insecticides in turf soils.  J. Econ. Entomol. 52:
  289-293.
Lichtenstein, E. P. and K. R. Schulz; 1959a.  Breakdown of lindane and
  aldrin in soils.  J. Econ. Entomol. 52:118-124.
Lichtenstein, E. P. and K. R. Schulz; 1959b.  Persistence of some chlor-
  inated hydrocarbon insecticides as influenced by soil types, rate of
  application and temperature.  J. Econ. Entomol. 52:124-131.
Lichtenstein, E. P. and K. R. Schulz; 1960.  Epoxidation of aldrin and
  heptachlor in soils as influenced by autoclaving, moisture, and soil
  types.  J. Econ. Entomol. 53:192-197.
Lichtenstein, E. P. and K. R. Schulz; 1965.  Residues of aldrin and
  heptachlor in soils and their translocation into various crops.  J.
  Agr. Food Chem. 13:57-63.
Lichtenstein, E. P., L. J. DePew, E. L. Eshbaugh and J. P. Sleesman;
  1960.  Persistence of DDT, aldrin, and lindane in some midwesterti
  soils.  J. Econ. Entomol. 53:136-144.
                                  386

-------
Lichtenstein, E. P., T. W. Fuhremann, K. R. Schulz and R. F. Skrentny;
  1967.  Effect of detergents and inorganic salts in water on the per-
  sistence and movement of insecticides in soils.  J. Econ. Entomol.
  60:1714.
Lichtenstein, E. P., W. F. Millington and G. T. Cowley; 1962a.  Effect
  of various insecticides on growth and respiration of plants.  J. Agr.
  Food Chem. 10:251-256.
Lichtenstein, E. P., C. H. Mueller, G. R. Myrdal and K. R. Schulz; 1962b.
  Vertical distribution and persistence of insecticidal residues in
  soils as influenced by mode of application and a cover crop.  J. Econ.
  Entomol. 55:215-219.
Lichtenstein, E. P., G. R. Myrdal and K. R. Schulz; 1964.  Effect of
  formulation and mode of application of aldrin on the loss of aldrin
  and its epoxide from soils and their translocation into carrots.  J.
  Econ. Entomol. 57:133-136.
Lichtenstein, E. P., J. P. Anderson, T. W. Fuhremann and K. R. Schulz;
  1968a.  Aldrin and dieldrin:  loss under sterile conditions.  Science
  159:1110-1111.
Lichtenstein, E. P., T. W. Fuhremann, and K. R. Schulz; 1968b.  Use of
  carbon to reduce the uptake of insecticidal soil residues by crop
  plants.  Effects of carbon on insecticide adsorption and toxicity in
  soils.  J. Agr. Food Chem. 16:348-355.
Lichtenstein, E. P., K. R. Schulz, T. W. Fuhremann and T. T., Liang;
  1970.  Degradation of aldrin and heptachlor in field soils during a
  10 year period.  J. Agr. Food Chem. 18:100-106.
Lichtenstein, E. P., T. W. Fuhremann and K. R. Schulz; 1971a.  Persis-
  tence and vertical distribution of DDT, lindane, and aldrin residues,
  ten and 15 years after single soil application.  J. Agr. Food Chem.
  19:718-721.
Lichtenstein, E. P., K. R. Schulz and T. W. Fuhremann; 1971b.  Effects
  of cover crop vs. soil cultivation on the fate and vertical distri-
  bution of insecticide residues in soil, 7 to 11 years after soil treat-
                                   387

-------
  ment.  Pestic. Monit. J. 5:215-222.
Lichtenstein, E. P., K. R. Schulz and T. W. Fuhremann; 1971c.  Long-
  term effects of carbon in reducing uptake of insecticidal soil resi-
  dues by crops.  J. Econ. Entomol. 64:585-588.
Lidgate, H. J.; 1967.  Earthworm control with chlordane.  J. Sportsturf
  Res. Ind. 1966, 42:5-8. (Chem. Abstr. 70:10592d, 1969).
Lillie, R. J., H. C. Cecil and J. Bitman; 1973.  Methoxychlor in chick-
  en breeder diets.  Poult. Sci. 52:1134-1138.
Lippold, P. C., J. S. Cleere, L. M. Massey, Jr., J. B. Bourke and A. W.
  Avens; 1969.  Degradation of insecticides by cobalt-60 gamma radia-
  tion.  J. Econ. Entomol. 62:1509-1560.
Lloyd-Jones, C. P.; 1971.  Evaporation of DDT.  Nature 229:65-66.
                                                                    14
Lopes-Gonzalez, J. D. and C. Gonzalez-Gomez; 1970.  Leaching of DDT-  C
  from homoionic clays using water.  An. Quim. 66:271-282. (Chem.
  Abstr. 73:119588v, 1970).
Lowe, J. I., P. D. Wilson, A. J. Rick, A. J. Wilson and J. Alfred, Jr.;
  1970.  Chronic exposure of oysters to DDT, toxaphene, and parathion.
  Proc. Nat. Shellfish Assoc. 61:71-79. (Chem. Abstr. 75:128793b, 1971).
Lu, P-Y., R. L. Metcalf, A. S. Hirwe and J. W. Williams; 1975.  Evalua-
  tion of environmental distribution and fate of hexachlorocyclopenta-
  diene, chlordene, heptachlor, and heptachlor epoxide in a laboratory
  model ecosystem.  J. Agr. Food Chem. 23:967-972.
Luchev, I., S. Danon, T. Kuyumdziheva and G. Dzhedzheva; 1971.  Criteria
  for standardization of pesticide levels in soil.  Roca. Panstw. Zakl.
  Hig. 22:33-37. (Chem. Abstr. 75:4516u, 1971).
Luczak, J.; 1969.  Stability of methoxychlor in natural waters.  Rocz.
  Panstw. Hig. 20:147-154. (Chem. Abstr. 71:53307c, 1969).
Ludke, J. L., 11. T. Finley and C. Lusk; 1971.  Toxicity of mirex to
  crayfish, Procambarus blandingii.  Bull. Environ. Contain. Toxicol,.
  6:89-96.
Luedemann, D. and H. Neumann; 1962.  Uber die Wirkung der Neuzeitlichen
  Kontaktinsectizide auf die Tiere des Stisswassers.  Anz. Schadlings-
  kunde 35:5-9.
                                  388

-------
Lutz-Ostertag, Y. and J. P. Kantelip; 1971.  Action sterilisante de
  1'endosulfan (Thiodan) (insecticide organochlore") sur les gonads de
  1'embryon de poulet et de caille in vivo and in vitro.  C. R. Soc.
  Biol. 165:844-848.
Macek, K. J., C. Hutchinson and 0. B. Cope; 1969.  Effects of tempera-
  ture on the susceptibility of blue-gills and rainbow trout to selec-
  ted pesticides.  Bull. Environ. Contain. Toxicol. 4:174-183.
Macek, K. J. and W. A. McAllister; 1970.  Insecticide susceptibility
  of some common fish family representatives.  Trans. Amer. Fish Soc.
  99:20-27.
MacGregor, J. S.; 1974.  Changes in the amount and proportions of DDT
  and its metabolites, DDE and DDD, in the marine environment off
  southern California.  Nat. Oceanic Atmos. Admin. (U.S.), Fish Bull.
  72:27-293. (Chem. Abstr. 81:58986q, 1974).
MacLang, F. A.; 1967.  Persistence of aldrin and dieldrin in soils.
  Sugar News 43:135-136, 138, 140. (Chem. Abstr. 68:21169f, 1968).
Mackay, D. and A. W. Wolkoff; 1973.  Rates of evaporation of low-solu-
  bility contaminants from water bodies to atmosphere.  Environ. Sci.
  Technol. 7:611-614.
MacPhee, A. W., D. Chisolm and C. R. MacEachern; 1960.  Persistence of
  certain pesticides in the soil and their effect on crop yeilds.  Can.
  J. Soil Sci. 40 No. 1:59-62.
Mahmoud, S. A. Z., K. G. Selim and M. T. El-Mokadem; 1970.  Effect of
  dieldrin and lindane on soil microorganisms.  Zentralbl. Bakteriol.,
  Parasitenk., Infektionskr. Hyg., Abt. 2: 125:134-149.
Maier-Bode, H.; 1966.  The persistence of the insecticide endosulfan in
  plants and animals.  Meded. Rijksfac. Landbouwwetensch., Gent 31:506-
  510. (Chem. Abstr. 69:75892a, 1968).
Malecki, R. A., S. A. Allen and J. 0. Elliston; 1974.  Cottontail re-
  production related to dieldrin exposure.  U.S. Fish Wildl. Serv.
  Spec. Sci. Rep. Wildl. 177, 61 pp.
Markaryan, D. S.; 1972.  Mutagenic characteristics of organochlorine
                                  389

-------
  pesticides in primates and small laboratory animals.  Vop. Gig.
  Normirovaniya Izuch. Otdalennykh Posledstvii Vosdeistv. Prom.
  Veshchestv. 24-40.
Markin, G., J. H. Ford and J. C. Hawthorne; 1972.  Mirex residues in
  wild populations of the edible red crawfish (Procambarus alarkii).
  Bull. Environ. Contam. Toxicol. 8:369-.
Marston, R. B. , R. M. Tyo and S. C. Middendorf;  1969.  Endrin in water
  from treated Douglas fir seed.  Pestic. Monit. J. 2:167-175.
Martens, R.; 1972.  Decomposition of endosulfan by soil microorganisms.
  Schriftner, Ver. Wasser-, Boden-, Lufthyg., Berlin-Da'hlem, No. 37:
  167-173. (Chem. Abstr. 78:156400b, 1973).
Martin, H.; 1968.  Pesticide Manual.  British Crop Protection Council.
Martin, J. P., R. B. Harding, G. H. Cannell and L. D. Anderson; 1959.
  Influence of five annual field applications of organic insecticides
  on soil biological and physical properties.  Soil Sci. 87:334-338.
Matsumura, F. and G. M. Boush; 1967.  Dieldrin:   degradation by soil
  microbes.  Science 156:959-961.
Matsumura, F. and G. M. Boush; 1968.  Degradation of insecticides by a
  soil fungus, Trichoderma viride.  J. Econ. Entomol. 61:610-612.
Matsumura, F. and G. M. Boush; 1971.  Metabolism of insecticides by
  microorganisms.  Soil Biochem. 2:320-336.
Matsumura, F. and G. M. Boush; 1972.  Metabolic transformation of DDT,
  dieldrin, aldrin, and endrin by marine microorganisms.  Environ. Sci.
  Technol. 6:629-632.
Matsumura, F., G. M. Boush and A. Tai; 1968.  Breakdown of dieldrin in
  the soil by a microorganism.  Nature 219:965-967.
Matsumura, F., K. C. Patil and G. M. Boush; 1970.  Formation of photo-
  dieldrin by microorganisms.  Science 170:1206-1207.
Matsumura, F., V. G. Khanvilkar, K. C. Patil and G. M. Boush; 1971a.
  Metabolism of endrin by certain soil microorganisms.  J. Agr. Food
  Chem. 19:27-31.
                                  390

-------
Matsumura, F., K. C. Patil and G. M. Boush; 1971b.  DDT metabolized by
  microorganisms from Lake Michigan.  Nature 230:325-326.
Matsumura, F., R. W. Howard and J. 0. Nelson; 1975.  Structure of the
  toxic fraction A of toxaphene.  Chemosphere 4:271-276.
McCaskey, T. A., A. R. Stemp, B. J. Liska and W. J. Stadelman; 1968.
  Residues in egg yolks and raw and cooked tissues from laying hens
  administered selected chlorinated hydrocarbon pesticides.  Poultry
  Sci. 47:564-569.
McFarland, L. Z. and P. B. Lacy; 1969.  Physiologic and endocrinologic
  effects of the insecticide Kepone in the Japanese Quail.  Toxicol.
  Appl. Pharmacol. 15:441-450.
McKinely and H. C. Grice; 1960.  Identification of pesticide residues
  in extracts of fruit, vegetables, and animal fats. III. Metabolites
  of chlorinated hydrocarbon insecticides in animal depot fat.  J.
  Assoc. Offic. Agr. Chemists 43:725-731.
McLane, M. A. R., L. F. Stickel and J. D. Newsom; 1971.  Organochlorine
  pesticide residues in woodcock, soils, and earthworms in Louisiana,
  1965.  Pestic. Monit. J. 5:248-250.
McLaughlin, J., Jr., J. P. Marliac, M. J. Verrett, M. K. Mutchler and
  0. G. Fitzhugh; 1962.  The injection of chemicals into the yolk sac
  of fertile eggs prior to incubation as a toxicity test.  Toxicol.
  Appl. Pharmacol. 5:760-761.
Mehendale, H. M., L. Fishbein, M. Fields and H. B. Matthews; 1972.
                14
  Fate of mirex-  C in the rat and plants.  Bull. Environ. Contain.
  Toxicol. 8:200-207.
Mehrle, P. M. and F. L. Mayer, Jr.; 1975a.  Toxaphene effects on growth
  and bone composition of fathead minnows, Pi-mephales promelas.   J.
  Fish. Res. Board Can. 32:593-598.
Mehrle, P. M. and F. L. Mayer, Jr.; 1975b.  Toxaphene effects on growth
  and development of brook trout (Salvelinus fontinalis").  J. Fish Res.
  Board Can. 32:609-613.
                                  391

-------
Meksongsee, B., R. S. Yang and F. E. Guthrie; 1967.  Effect of inhibitors
  and inducers of microsomal enzymes on the toxicity of carbamate in-
  secticides to mice and insects.  J. Econ. Entomol. 60:1469-1471.
Mendel, J. L. and M. S. Walton; 1966.  Conversion of pjp'-DDT to p3pr-
  DDD by intestinal flora of the rat.  Science 151:1527-1528.
Menzel,  D. W., J. Anderson and A. Randtke; 1970.  Marine phytoplankton
  vary in their response to chlorinated hydrocarbons.  Science 167:
  1724-1726.
Menzie, C. M.; 1974.  Metabolism of pesticides: an update.  U.S. Dept.
  Int. Fish and Wildl. Serv. Sp. Sci. Rep. Wildl. 184:486 pp.
Merna, J. W. and P. J. Eisele; 1973.  Effects of methoxychlor on aquatic
  biota.  U.S. Nat. Tech. Inform. Serv., PB Rep. //228643/3GA, 66 pp. GPO,
  80.95.
Mestitsova, M.; 1967.  Reproduction studies and the occurrence of cata-
  racts in rats after long-term feeding of the insecticide heptachlor.
  Experientia 23:42-43.
Metcalf, R. L., G. K. Sangha and I. P. Kapoor; 1971.  Model ecosystem
  for the evaluation of pesticide biodegradability and ecological mag-
  nification.  Environ. Sci. Technol. 5:709-713.
Metcalf, R. L., I. P. Kapoor, P-Y Lu, C. K. Schuth and P. Sherman; 1973.
  Model ecosystem studies of the environmental fate of six organochlorine
  pesticides.  Environ. Health Perspect. 1973:35-44.
Metcalf, R. L., J. R. Sanborn, P-Y Lu, and D. Nye; 1975.  Laboratory
  model ecosystem studies of the degradation and fate of radiolabeled
  tri-, tetra-, and pentachlorobiphenyl compared with DDE.  Arch.
  Environ. Contam. Toxicol. 3:151-165.
Miles, J. R. W. and C. R. Harris; 1971.  Insecticide residues in a
  stream and a controlled drainage system in agricultural areas of
  southwestern Ontario.  Pestic. Monit. J. 5:289-294.
Miles, J. R., C. M. Ming and C. R. Harris; 1969.  Metabolism of hepta-
  chlor and its degradation products by soil microorganisms.  J. Econ.
  Entomol. 62:1334-1338.
                                   392

-------
Miles, J. R. W., C. M. Tu and C. R. Harris; 1971.  Degradation of hepta-
  chlor epoxide and heptachlor by a mixed culture of soil microorgan-
  isms.  J. Econ. Entomol. 64:839-941.
Mistric, W. J. and J. C. Gaines; 1953.  Effect of wind and other factors
  on the toxicity of certain insecticides.  J. Econ. Entomol. 46:341-
  349.
Miyazaki, S. and A. J. Thorsteinson; 1972.  Metabolism of DDT by fresh-
  water diatoms.  Bull. Environ. Contam. Toxicol. 8:81-83.
Mizyukova, I. G. and G. V. Kurchatov; 1970.  Metabolism of heptachlor.
  Farmakol. Toksikol. 33:496-499. (Chem. Abstr. 73:86885j, 1970).
Morgan, L. W., D. B. Leuck, E. W. Beck and D. W. Woodham; 1967.  Resi-
  dues of aldrin, chlordane, endrin, and heptachlor in peanuts grown in
  treated soil.  J. Econ. Entomol. 60:1289-1291.
Morgan, D. P. and C. C. Roan; 1971.  Absorption, storage, and metabolic
  conversion of ingested DDT and DDT metabolites in man.  Arch. Environ.
  Health 22:301-308.
Morley, H. V. and M. Chiba; 1965.  Dieldrin uptake from soil by wheat
  plants.  Can. J. Plant Sci. 45:209-210.
Morris, R. L. and L. G. Johnson; 1971.  Dieldrin levels in fish from
  Iowa streams.  Pestic. Monit. J. 5:12-16.
Mosier, A. R., W. D. Guenzi and L. L. Miller; 1969.  Photochemical de-
  composition of DDT by a free-radical mechanism.  Science 164:1083-
  1085.
Moubry, R. J., J. M. Helm and G. R. Myrdal; 1968.  Chlorinated pesti-
  cide residues in an aquatic environment located adjacent to a com-
  mercial orchard.  Pestic. Monit. J.;  l(4):27-29.
Moye, W. C. and W. H. Luckman; 1964.  Fluctuations in populations of
  certain aquatic insects following application of aldrin granules to
  Sugar Creek, Iroquois County, Illinois.  J. Econ. Entomol. 57:318-
  322.
Moza, P., I. Weisgerber and W. Klein; 1972.  BeitrSge zur Bkologischen
                                                     14
  Chemie L.  Auswaschen eines wasserlb'slichen Aldrin-  C-Abbauprodukts
                                   393

-------
  aus Boden.  Chemosphere 1:191-195.
Mueller, W. P. and F. Korte; 1975.  Contributions to ecological chemis-
  try CII.  Microbial degradation of benzo-(a)-pyrene, monolinuron, and
  dieldrin in waste composting.  Chemosphere 4:195-198.
Mulla, M. S.; 1960a.  Loss of chlorinated hydrocarbon insecticides from
  soil surface in the field.  J. Econ. Entomol. 53:650-659.
Mulla, M. S.; 1960b.  Loss of activity of chlorinated hydrocarbon insec-
  ticides in soil as measured against the eye gnat, Hippelates collusor.
  J. Econ. Entomol. 53:785-788.
Mulla, M. S.; 1962.  Frog and toad control with insecticides.  Pest
  Control 30: October, p. 20.
Mulla, M. S., L. W. Isaak and H. Axelrod; 1963.  Field studies on the
  effects of insecticides on some aquatic wildlife species. J. Econ.
  Entomol. 56:184-188.
Muller, W., G. Nohynek, G. Woods, F. Korte and F. Coulston; 1975.  Com-
                                  14
  parative metabolism of dieldrin-  C in mouse, rat, rabbit, rhesus
  monkey and chimpanzee.  Chemosphere 4:89-92.
Mullins, D. E., R. E. Johnsen and R. I. Starr; 1971.  Persistence of
  organochlorine insecticide residues in agricultural soils of Colo-
  rado.  Pestic. Monit. J. 5:268-275.
Murado-Garcia, M. A., G. Baluia Marcos; 1973.  Metabolism of aldrin by
  Penieilliion funiculosion.  Rev. Agroquim. Tecnol. Aliment. 13:559-566.
  (Chem. Abstr. 81:34208m, 1974).
Naishtein, S. Y., E. I. Yurovskaya, N. P. Vashkulat; 1967.  Pesticides
  in the soil as a possible factor of the pollution of groundwaters and
  open reservoirs.  Vop. Gig. Toksikol. Pestits., Tr. Nauch. Sess. Akad.
  Med. Nauk SSR 1967:225-228. (Chem. Abstr. 74:139991v, 1971).
Nakamura, N.; 1960.  Chronic poisoning by various insecticides in rats.
  Nippon Yakurigaku Zasshi 56:829-849. (Chem. Abstr. 55:22605g, 1961).
Naqvi, S. M. and D. E. Ferguson; 1968.  Pesticide tolerances of selec-
  ted freshwater invertebrates.  J. Miss. Acad. Sci. 14:121-127.  (Chem.
  Abstr. 72:65811w, 1970).
                                   394

-------
Nash, R. G.; 1968.  Plant absorption of dieldrin, DDT and endrin from
  soils.  Agron. J. 60:217-219.
Nash, R. G. and W. G. Harris; 1973.  Chlorinated hydrocarbon insecti-
  cide residues in crops and soils.  J. Environ. Qual. 2:269-273.
Nash, R. G. and E. A. Woolson; 1967.  Persistence of chlorinated hydro-
  carbon insecticides in soils.  Science 157:924-927.
Nash, R. G. and E. A. Woolson; 1968.  Distribution of chlorinated in-
  secticides in cultivated soil.  Soil Sci. Soc. Amer., Proc. 32:525-
  527.
Nash, R. G., M. L. Beall, Jr., and W. G. Harris; 1972.  Endrin trans-
  formations in soil.  J. Environ. Qual. 1:391-394.
Nelson, J. A.; 1974.  Effects of dichlorodiphenyltrichloroethane (DDT)
  analogs and polychlorinated biphenyl (PCB) mixtures on 17 (3-estradiol-
  3
   H to rat uterine receptor.  Biochem. Pharmacol. 23:447-451.
Nelson, J. 0. and F. Matsumura; 1975.  A simplified approach to studies
  of toxic toxaphene compounds.  Bull. Environ. Contain. Toxicol. 13:
  464-470.
Nelson, B. D. and C. Williams; 1971.  Action of cyclodiene pesticides
  on oxidative metabolism in the yeast Saceharomyces ceTevls-Lae.  J.
  Agr. Food Chem. 19:339-341.
Neudorf, S. and M. A. Q. Khan; 1975.  Pick up and metabolism of DDT,
  dieldrin, and photodieldrin by a fresh water alga  (Arikistrodesmus
  amalloides') and a microcrustacean  (Daphnia pulex).  Bull. Environ.
  Contain. Toxicol. 13:443-450.
Nishimura, H.; 1973.  Teratogenic substances.  Int. Chem. Eng. 13:774-
  780.
Noda, K., M. Hirabayashi, I. Yonemura, M. Maruyama and I. Endo; 1972.
  Endrin.  Oyo Yakuri 6:673-679. (Chem. Abstr. 78:38963q, 1973).
Obuchowska, I.; 1969.  Stability of methoxychlor in the soil.  Roca.
  Panstw. Zakl. Hig. 20:489-493.  (Chem. Abstr. 72:89234m, 1972).
Obuchowska, I.; 1972.  Behavior of Tritox-30 in soil.  Roca. Panstw.
  Zakl. Hig. 23:147-154. (Chem. Abstr. 77:57592p, 1972).
                                  395

-------
Ohsawa, T., J. R. Knox, S. Khalifa and J. E. Casida; 1975.  Metabolic
  dechlorination of toxaphene in rats.  J. Agr. Food Chem. 23:98-106.
Okey, A. B.; 1972.  Dimethylbenzanthracene-induced mammary tumors in
  rats.  Inhibition by DDT.  Life Sci. 11(17)(Pt. l):833-843.
Olney, C. E., W. E. Donaldson and T. W. Kerr; 1962.  Methoxychlor in
  eggs and chicken tissues.  J. Econ. Entomol.  55:477-479.
Onuska, F. I. and M. E. Comba; 1975.  Isolation and characterization of
  the photoalteration products of oi-s- and trans-chlordan.  Assoc. Off.
  Anal. Chem., J. 58:6-9.
Ottolenghi, A. D., J. Haseman and F. Suggs; 1974.  Teratogenic effects
  of aldrin, dieldrin and endrin in hamsters and mice.  Teratology 9:
  11-16.
Ozburn, G. W. and F. 0. Morrison; 1964.  A DDT-tolerant strain of mice.
  Can. J. Zool. 42:519-526.
Palmer, K. A., S. Green and M. S. Legator; 1973.  Dominant lethal study
  of p^p'-DDT in rats.  Food Cosmet. Toxicol. 11:53-62.
Palmer, K. J., R. Y. Wong, R. E. Lundin, S. Khalifa and J. E. Casida;
  1975.  Crystal and molecular structure of 2,2,5-endo3 6-exo, 8,9,10-
  heptachlorobornane, ciQHllC7' a toxic component of toxaphene insec-
  ticide.  J. Am. Chem. Soc. 97:408-413.
Paris, D. F. and D. L. Lewis; 1973.  Chemical and microbial degradation
  of ten selected pesticides in aquatic systems.  Residue Rev. 45:95-
  124.
Park, P. 0. and C. E. McKone; 1966.  Persistence and distribution of
  soil-applied insecticides in an irrigated soil in Northern Tanzania.
  Trop. Agr. 43:133-142.
Parlar, H. and F. Korte: 1973.  BeitrMge zur Skologischen Chemie LX.
  Zur Photochemie der Chlordanderivate.  Chemisphere 2:169-172.
Parr, J. F., G. H. Willis and S. Smith; 1970.  Soil anaerobiosis.  II.
  Effect of selected environments and energy sources on the degrada-
  tion of DDT.  Soil. Sci. 110:306-312.
                                  396

-------
Parr, J. F. and S. Smith; 1974.  Degradation of DDT in an everglades
  muck as affected by lime, ferrous iron, and anaerobiosis.  Soil Sci.
  118:45-52.
Parsenyuk, L. N. and V. Y. Akimenko; 1970.  Effect of DDT on the redox
  potential of the soil.  Faktory Vnesh. Sredy Ikh Znachenie Zdorov'ya
  Naseleniya 2:137-140. (Chem. Abstr. 75:19140r, 1971).
Pathak, A. N., H. Shankar and K. S. Awasthi; 1961.  Effect of some pes-
  ticides on available nutrients and soil microflora.  J. Indian Soc.
  Soil Sci. 9:197-200. (Chem. Abstr. 56:7750g, 1962).
Patil, K. C. and F. Matsumura; 1970.  Degradation of endrin, aldrin, and
  DDT by soil microorganisms.  Appl. Microbiol. 19:879-881.
Patil, K. C., F. Matsumura and G. M. Boush; 1972.  Metabolic transfor-
  mation of DDT, dieldrin, aldrin, and endrin by marine microorganisms.
  Environ. Sci. Technol. 6:629-632.
Paulini, E.; 1957.  Adsorption of DDT by clay.  Bol. Ofic. Sanit. Panam.
 .43:433-438. (Chem. Abstr. 52:17599b, 1958).
Peach, M. E., J. P. Schaffner and D. A. Stiles; 1973.  Movement of ald-
  rin and heptachlor residues in a sloping field of sandy loam textures.
  Can. J. Soil Sci. 53:459-463.
Peakall, D. B.; 1975.  in: Environmental Dynamics of PesticideS3 343-
  360.  R. Haque and V. H. Freed, ed.; Plenum Press, N.Y. and London.
  Physiological effects of chlorinated hydrocarbons on avian species.
Peeters, J. F., A. R. Van Rossen, K. A. Heremans and L. Delcambe; 1975.
  Influence of pesticides on the presence and activity of nitrogenase
  in Azobacter vinelandii.  J. Agr. Food Chem. 23:404-406.
Peri, G.; 1952.  Insecticide action on soil microflora.  Ann. Fitopatol.
  1:47-57. (Chem. Abstr. 47:2411, 1953).
Perscheid, M., H. Schlueter and K. Ballschmiter; 1973.  Aerober Abbau
  von Endosulfan durch Bodenmikroorganismen.  Z. Naturforsch., Teil C
  28:761-763.
                                  397

-------
Persin, S. A.; 1961.  The influence of chlorinated-organic compounds on
  soil fertility and on crop yields.  Pochvovedenie 1961, No. 9:91-99.
  (Chem. Abstr. 56:10614b, 1962).
Petrocelli, S. R.,  J. W. Anderson and A. R. Hanks; 1975.  Biomagnifi-
  cation of dieldrin residues by food-chain transfer from clams to
  blue crabs under controlled conditions.  Bull. Environ. Contam. Toxi-
  col. 13:108-116.
Pfaender, F. K. and M. Alexander; 1973.  Effect of nutrient additions
  on the apparent cometabolism of DDT.  J. Agr. Food Chem. 21:397-399.
Pfister, R. M.; 1971.  Influence of suspended microscopic substances on
  the metabolic activities of microorganisms responsible for biological
  enrichment of water.  U.S. Nat. Tech. Inform. Serv. PB Rep. #202581,
  124 pp.
Phillips, F. T.; 1971.  Persistence of organochlorine insecticides on
  different substrates under different environmental conditions.  I.
  Rates of loss of dieldrin and aldrin by volatilization from glass
  surfaces.  Pest.  Sci. 2:255-266.
Phillips, J. H., E. E. Haderlie and W. L. Lee; 1975.  An analysis of
  the dynamics of DDT in marine sediments.  EPA Ecological Research
  series:  EPA-660/3-75-013.
Phillips, W. E. J.  and G. Hatina; 1972.  Effect of dietary organochlo-
  rine pesticides on the liver vitamin A of the weanling rat.  Nutr.
  Rep. Int. 5:357-362.  (Chem. Abstr. 77:71073b, 1972).
Piasecki, J., J. Wybieralski, A. Wybieralska; 1970.  Effect of ultra-
  violet radiation on DDT and HCH content in soils with various physio-
  chemical properties.  Zesz. Nauk. Wyzsz. Szk. Roln. Szczecinie 6:251-
  262. (Chem. Abstr. 75:19138w, 1971).
Pielou, D. P.; 1946.  Lethal effect of DDT on young fish.  Nature 158:
  378.
Pierce, R. H., Jr., C. E. Olney and G. T. Felbeck, Jr.; 1974.  p3p '-DDT
  adsorption  to suspended particulate matter in sea water.  Geochim.
  Cosmochim. Acta 38:1061-1073.  (Chem. Abstr. 82:12252q, 1975).
                                   398

-------
Pimentel, D.; 1971.  Ecological effects of pesticides on non-target
  species.  U.S. Gov't Printing Office #4106-0029.
Plimmer, J. R., P. C. Kearney and D. W. VonEndt; 1968.  Mechanism of
  conversion of DDT to DDD by AeTobaoteT aerogenee.  J. Agr. Food Chem.
  16:594-597.
Polizu, A., S. Floru and F. Paulian; 1971.  Translocation and distribu-
  tion of heptachlor, aldrin, and dieldrin in the corn plant.  Qual.
  Plant. Mater. Veg. 20:329-339. (Chem. Abstr. 76:108908k, 1972).
Polizu, A., M. Roman and G. Boguleanu; 1972.  Aldrin, dieldrin, and
  heptachlor persistence in soil and accumulation of residues in pota-
  to tubers following soil applications.  An. Inst. Gercet. Prot.
  Plant., Acad. Stiinte Agr. Silvice 1970. (Chem. Abstr. 79:1182d, 1973).
Popov, P. V. and L. Donev; 1970.  Residual effects of insecticides ap-
  plied into the soil.  Acta. Agron. (Budapest) 19:89-96. (Chem. Abstr.
  73:75748r, 1970).
Poppe, J.; 1966.  Tolerance of mushroom mycelium to some insecticides
  and acaricides.  Meded. Rijksfac. Landbouwwetensch. Gen. 31:995-1004.
  (Chem. Abstr. 69:6647q, 1968).
Porter, L. K. and W. E. Beard; 1968.  Retention and volatilization of
  lindane and DDT in the presence of organic colloids isolated from
  soils and leonardite.  J. Agr. Food Chem. 16:344-347.
Probst, A. H. and R. T. Everly; 1957.  Effect of soil insecticides on
  emergence, growth, yield, and chemical composition of soybeans.  Agron.
  J. 49:385-387.
Prospero, J. M. and D. B. Seba; 1972.  Additional measurements of pes-
  ticides in the lower atmosphere of the northern equatorial Atlantic
  Ocean.  Atmos. Environ. 6:363-364.
Radomski, J. L., W. B. Deichmann, E. E. Clizer and A. Ray; 1968.  Pes-
  ticide concentrations in the liver, brain, and adipose tissue of ter-
  minal hospital patients.  Food Cosmet. Toxicol. 6:209-220. (Chem.
  Abstr. 69:66426z, 1968).
                                   399

-------
Radomski, J. L., W. B. Deichmann, W. E. MacDonald and E. M. Glass; 1965.
  Synergism among oral carcinogens.  I. Results of the simultaneous
  feeding of four tumorigens to rats.  Toxicol. Appl. Pharmacol. 7:652-
  656.
Raman, S. and K. K. Krishnamoorthy; 1973.  Decomposition of the active
  ingredient of pesticides during storage.  Pesticides 7:20.
Randolph, N. M., R. D. Chisholm, L. Koblitsky and J. C. Gaines; 1960.
  Insecticide residues in certain Texas soils.  Texas Agr. Expt. Sta.
  MP-477, 11 pp. (Chem. Abstr. 55:4868a, 1961).
Rankov, V. and E. Khristova; 1971.  Effect of some insecticides on soil
  microflora.  Sel'skokhoz. Biol. 6:288-291. (Chem. Abstr. 74:l39970n,
  1971).
Rautapaa, J., H. Siltanen, A. L. Yalta, V. Mattinen; 1972.  DDT, lin-
  dane, and endrin in some agricultural soils in Finland.  Maataloustiet.
  Aikak. 44:199-206, 1972. (Chem. Abstr. 78:109845r, 1973).
Reddy, G. and M. A. Q. Khan; 1975.  Fate of photodieldrin under various
  environmental conditions.  Bull. Environ. Contain. Toxicol. 13:64-72,.
Reed, J. K.; 1969.   Interaction of pesticide pollutants and aquatic
  food chain organisms.  U.S. Clearinghouse Fed. Sci. Tech. Inform. PB
  REP #188794, 18 pp.
Reimold, R. J. and C. J. Durant; 1974.  Toxaphene content of estuarine
  fauna and flora before, during, and after dredging toxaphene-contami-
  nated sediments.   Pestic. Honit. J. 8:44-49.
Reinbold, K. A., I. P. Kapoor, W. F. Childers, W. N. Bruce and R. L.
  Metcalf; 1971.  Comparative uptake and biodegradability of DDT and
  methoxychlor by aquatic organisms.  111. Nat. Hist. Surv. Bull. 30:
  405-417.
Reinert, R. E.; 1970.  Pesticide concentrations in Great Lakes fish.
  Pestic. Monit. J. 3:233-240.
Reynolds, H. T., T. R. Fukuto, R. L. Metcalf and R. B. March; 1957.
  Seed treatment of field crops with systemic insecticides.  J. Econ.
  Entomo. 50:527-539.
                                   400

-------
Richardson, E. M. and E. Epstein; 1971.  Retention of three insecti-
  cides on different size soil particles suspended in water.  Soil Sci.
  Soc. Amer., Proc. 35:884-887.
Richardson, L. T. and D. M. Miller; 1960.  Fungitoxicity of chlorinated
  hydrocarbon insecticides in relation to water solubility and vapor
  pressure.  Can. J. Botany 38:163-175.
Riekerk, H. and S. P. Gessel; 1968.  Movement of DDT in forest soil so-
  lutions.  Soil Sci. Soc. Amer., Proc. 32:595-596.
Risebrough, R. W., R. J. Hugget, J. J. Griffin and E. D. Goldberg; 1968.
  Pesticides:  transatlantic movements in the Northeast Trades.  Science
  159:1233-1236.
Roberts, D.; 1975.  Differential uptake of endosulfan by the tissues of
  Mytilus edulis.  Bull. Environ. Contain. Toxicol. 13:170-176.
Roberts, J. E. and W. B. Bollen; 1955.  A microplating method for soil
  molds and its use to detect some effects of certain insecticides and
  herbicides.  Appl. Microbiol. 3:190-194.
Rosen, J. D. and D. J. Sutherland; 1967.  The nature and toxicity of
  the photoconversion products of aldrin.  Bull. Environ. Contain.
  Toxicol. 2:1-9.
Roemer-Maehler, J., D. Bieniek and F. Korte; 1973.  BeitrSge zur okolo-
  gischen Chemie LIV.  Solvolyse von Heptachlor und Dieldrin unter
  hohen Drucken.  Chemosphere 2:31-33.
Rosenberg, D. M.; 1975.  Fate of dieldrin in sediment, water, vegeta-
  tion, and invertebrates of a slough in central Alberta, Canada.
  Quaest. Ent. 11:69-96.
Rosival, L. ; 1970.  Mutagenic effects of pesticides.  Agrochemia 10:12.
  (Chem. Abstr. 74:98848h, 1971).
Ross, D. J.; 1974.  Influence of four pesticide formulations on micro-
  bial processes in a New Zealand pasture soil.  II. Nitrogen minerali-
  zation.  N. Z. J. Agr. Res. 17:9-17.
Saha, J. G. and Y. W. Lee; 1970.  Metabolic fate of dieldrin-1 C in
  wheat plants and in soil.  J. Econ. Entomol. 63:670-671.
                                  401

-------
Saha, J. G. and A. K. Sumner; 1971.  Organochlorine insecticide resi-
  dues in soil from vegetable farms in Saskatchewan.  Pestic. Monit. J.
  5:28-31.
Saha, J. G., C. H. Craig and W. K. Janzen; 1968.  Organochlorine resi-
  dues in agricultural soil and legume crops in northeastern Saskatche-
  wan.  J. Agr. Food Chem. 16:617-619.
Salonius, P. 0.; 1972.  Effect of DDT and fenitrothion on forest-soil
  microflora.  J.  Econ.  Entomol. 65:1089-1090.
Sanborn, J. R.; 1974.  The fate of select pesticides in the aquatic en-
  vironment.  EPA Ecological Research Series.  U.S. Gov't Printing
  Office #5501-00995.
Sanborn, J. R. and C. C. Yu; 1973.  Fate of dieldrin in a model ecosys-
  tem.  Bull. Environ. Contain. Toxicol.  10:340-346.
Sanborn, J. R., R. L. Metcalf, W. N.  Bruce and P. Y. Lu; 1976.  The fate
  of chlordane and toxaphene in a terrestrial-aquatic model ecosystem.
  Environmental Entomology (in press).
Sandrock, K., D. Bieniek, W. Klein and F. Korte; 1974.  Beitrage zur
  b'kologischen Chemie LXXXVI:  Isolierung und Strukturaufklarung von
          14
  Kelevan-  C-Metaboliten und Bilanz  in Kartoffeln und Boden.  Chemo-
  sphere 3:199-204.
Sazonov, P. V. and Y. N. Chikhacheva; 1972.  Persistence of granulated
  heptachlor in soil.  Tr. Vses. Nauchno-Issled. Inst. Zashch. Rast.
  35:63-67. (Chem. Abstr. 83:2182y, 1975).
Scalf, M. R., W. J. Dunlap, L. G. McMillion and J. W. Keeley; 1969.
  Movement of DDT  (l,l,l-trichloro-2,2-Ms(p-chlorophenyl)ethane) and
  nitrates during groundwater recharge.   Water Resour. Res. 5:1041-
  1052.
Schafer, E. W.; 1972.  Acute oral toxicity of 369 pesticidal, pharma-
  ceutical, and other chemicals to wild birds.  Toxicol. Appl. Pharma-
  col. 21:315-330.
Schindler, U.; 1956.  Vole control experiments.  Z. Pflanzenkrankh. u.
  Pflanzenschutz.  63:694-704.  (Chem.  Abstr. 53:22710b, 1959).
                                  402

-------
Schmidt, R.; 1973.  Effect of l,l,l-trichloro-2,2-bis(p-chlorophenyl)^
  ethane (DDT) on the prenatal development of the mouse (under consid-
  eration of distribution and metabolism of tritium-labeled and carbon^
  14-labeled DDT in pregnant mice).  Biol. Rundsch. 11:316-317. (Chem.
  Abstr. 80:116895b, 1974).
Schoettger, R. A.; 1970.  Toxicology of Thiodan in several fish and
  aquatic invertebrates.  Invest. Fish Contr. No. 35, 31 pp. (Chem.
  Abstr. 73:119606z, 1970).
Schultz, C. D., W. L. Yauger and A. Bevenue; 1975.  Pesticides in fish
  from a Hawaiian canal.  Bull. Environ. Contain. Toxicol.  13:206-208.
Schumacher, G. , W. Klein and F. Korte; 1971.  Beitrage zur b'kologischen
  Chemie XXXII:  Photochemische Reaktionen des Endosulfans in Losung.
  Tetrahedron Letters.  2229-2232.
Schumacher, H. G., H. Parlar, W. Klein and F. Korte; 1973.  Beitrage
  zur b'kologischen Chemie LV.  Photochemische Reaktionen von Endosul-
  fan.  Chemosphere 2:65-68.
Schupan, I. and K. Ballschmiter; 1972.  Zur Persistenz von Hexachloro-
  bicyclo-(2,2,l)-hepten-Derivaten.  Fresenius' Z. Anal. Chem.  259:25-
  28.
Schupan, I., K. Ballschmiter and G. Toelg;  1968.  Zum Metabolismus des
  Endosulfans in Ratten und Mausen.  Z. Naturforsch. 23:701-705.
Selim, K. G., S. A. Z. Mahmoud, M. T. El-Mokadem; 1970.  Effect of diel-
  drin and lindane on the growth and nodulation of Vicia faba.   Plant
  Soil 33:325-329.
Servintuna, C.; 1963.  The acute toxicity of insecticides at oral and
  dermal application.  Bitki Koruna Bulteni 3:275-284. (Chem. Abstr.
  61:6246e, 1964).
Sethunathan, U. and T. Yoshida; 1973.  Degradation of chlorinated hy-
  drocarbons by clostridium species isolated from lindane-amended soil.
  Plant Soil 38:663-666.
Shabad, L.  M., T. S. Kolesnichenko and T. V. Nikonova; 1973.  Trans-
  placental and combined long-term effect of DDT in five generations
                                   403

-------
  of A-strain mice.  Int.  J.  Cancer 11:688-693.
Shamiyeh, N. B. and L. F.  Johnson; 1973.  Effect of heptachlor on num-
  bers of bacteria, actinomycetes, and fungi in soil.  Soil Biol. Bio-
  chem. 5:309-314.
Shaw, W. M. and B. Robinson;  1960.  Pesticide effects in soils on ni-
  trification and plant growth.   Soil Sci.  90:320-324.
Sherman, M. and M. M. R.osenberg; 1953.  Acute toxicity of four chlori-
  nated dimethanonaphthalene  insecticides to chicks.  J. Econ. Entomol.
  46:1067-1070.
Sherman, M. and M. M. Rosenberg; 1954.  Subchronic toxicity of four
  chlorinated dimethanonaphthalene insecticides to chicks.   J. Econ.
  Entomol. 47:1082-1083.
Shin; Y. 0., J. J. Chodan and A. R. Wolcott; 1970.  Adsorption of DDT
  by soils, soil fractions, and  biological materials.  J. Agr. Food
  Chem. 18:1129-1133.
Simal, J., J. Creus, A. Charro,  M. A. Boado, R.  Diaz and D. Vilas; 1971.
  Dieldrin content in fish, mollusks, and water of the Coruna, Betan-
  zos-Ares, and Ferrol Estuaries.  An. Bromatol. 1969-1970; 23:1-34.
  (Chem. Abstr. 76:149955s, 1972).
Smith, M. I., H. Bauer, E. F. Stohlman and R. D. Lillie; 1946.  Pharma-
  cologic action of certain analogs and derivatives of DDT.  J. Pharma-
  col. 88:359-365.
Smith, N. R. and M. E. Wenzel; 1947.  Soil microorganisms are affected
  by some of the new insecticides.  Soil Sci. Soc. Am., Proc. 12:227-
  233.
Smith, R. B., Jr., P. S. Larson, J. K. Finnegan, H. B.  Haag, G. R. Hen-
  nigar and F. Cobey; 1959.  Toxicological studies on l,l-bis(p-chloro-
  phenyl)-2,2,2-trichloroethanol  (Kelthane).  Toxicol.  Appl. Pharmacol.
  1:119-134.
Spalding, J. W., E. Ford,  D.  Lane and M. Blois; 1971.  Character of 1,1,
  l-trichloro-2,2-Z»ts (p-chlorophenyl)ethane.  Resistance in mouse L
  5178 Y lymphoma cells.  Biochem. Pharmacol. 11:3185-3196.
                                  404

-------
Speidel, H. K., A. W. Bourquin, J. E. Mann, J. F. Fair and E. 0. Bennett;
  1972.  Microbiological removal of pesticides from aqueous environments.
  Develop. Ind. Microbiol. 13:277-282.
Spence, J. H. and G. P. Markin; 1974.  Mirex residues in the physical
  environment following a single bait application, 1971-1972.  Pestic.
  Monit. J. 8:135-139.
Spencer, W. F.; 1975.  Movement of DDT and its derivatives into the
  atmosphere.  R.esidue Reviews 59:91-.
Spencer, W. F. and M. M. Cliath; 1972.  Volatility of DDT and related
  compounds.  J. Agr. Food Chem. 20:645-649.
Spencer, W. F. and M. M. Cliath; 1973.  Pesticide volatilization as
  related to water loss from soil.  J. Environ. Oual. 2:284-289.
Spencer, W. F., M. M. Cliath, W. J. Farmer and R. A. Shepherd; 1974.
  Volatility of DDT residues in soil as affected by flooding and or-
  ganic matter applications.  J. Environ. Oual. 3:126-129.
Spynu, E. I.; 1964.  Toxicology of new organic chlorinated insecticides
  obtained by diene synthesis with hexachlorocyclopentadiene.  Gigiena
  Truda i Prof. Zabolevaniya 8:30-35. (Chem. Abstr. 64:6299a, 1964).
Stadelman, W. J., B. J. Liska, B. E. Langlois , G. C. Mostert and A. R.
  Stemp; 1964.  Persistence of chlorinated hydrocarbon insecticide res-
  idues in chicken tissues and eggs.  Poultry Sci. 44:435-437.
Stadnyk, L., R. S. Campbell and B. T. Johnson; 1971.  Pesticide effect
  on growth and carbon-14 assimilation in a freshwater alga.  Bull.
  Environ. Contam. Toxicol. 6:1-8.
Stammers, F. M. G. and F. G. S. Whitefield; 1947.  Toxicity of DDT to
  man and animals.  Bull. Entomol. Res.  38:1-73.
Stanly, C. W., J. E. Barney, M. Helton and A. R. Yobs; 1971.  Measure-
  ment of atmospheric levels of pesticides.  Environ. Sci. Technol. 5:
  430-435.
Stevens, L. J., C. W. Collier and D. W.  Woodham; 1970.  Monitoring pes-
  ticides in soils from areas of regular, limited, and no pesticide use.
  Pestic. Monit. J. 4:145-164.
                                  405

-------
Stewart, D. K. R.;  1975.   Chlordane uptake from soil by root crops.
  Environ. Entomol. 4:254-256.
Stewart, D. K. R.  and K.  G. Cairns; 1974.   Endosulfan persistence in
  soil and uptake  by potato tubers.  J.  Agr.  Food Chem. 22:984-986.
Stewart, D. K. R.  and D.  Chisholm; 1971.  Long-term persistence of BHC,
  DDT, and chlordane in a sandy loam soil.  Can.  J. Soil Sci. 51:379-
  383.
Stewart, D. K. R.  and C.  J. S. Fox; 1971.   Persistence of organochlorine
  insecticides and their metabolites in Nova Scotian soils.  J. Econ.
  Entomol. 64:367-371.
Stewart, D. K. R.,  D. Chisholm and C. J. S. Fox;  1965.  Insecticide res-
  idues in potatoes and soil after consecutive soil treatments of al-
  drin and heptachlor.  Can. J. Plant Sci. 45:72-78.
Stickel, L. F.; 1973.  in: Environmental Pollution by Pesticides, pp.
  254-312.  C. A.  Edwards, ed.; Plenum Press, London.  Pesticide resi-
  dues in birds and mammals.
Stickel, W. H., L.  F. Stickel and J. W.  Spann; 1969.  Tissue residues
  of dieldrin in relation to mortality in birds and mammals.  Chemical
  Fallout 174-204.
Stickley, B. D. A.; 1972.  Persistence of aldrin, dieldrin, heptachlor,
  lindane, and crude BHC (hexachlorocyclohexane)  formulations in four
  Queensland soils.  Bur. Sugar. Exp. Sta., Queensl., Tech. Commun. #1,
  38 pp. (Chem. Abstr. 79:74711k, 1973).
Stickley, B. D. A.  and B. E. Hitchcock;  1972.  Dieldrin residues in the
  soil at harvest  of second and third ration crops.  Proc.  Queensl. Soc.
  Sugar Cane Technol. 39:257-259. (Chem. Abstr. 77:71427v,  1972).
Stitt, L. L. and J. Evanson; 1949.  Phytotoxicity and off-quality of
  vegetables grown in soil treated with insecticides.  J. Econ. Entomol.
  42:614-617.
Stojanovic, B. J.,  M. V.  Kennedy and F.  L. Shuman, Jr.: 1972a.  Edaphic
  aspects of the disposal of unused pesticides, pesticide wastes, and
  pesticide containers.  J. Environ. Qual. 1:54-62.
                                  406

-------
Stojanovic, B. J., F. Hutto, M. V. Kennedy and F. L. Shuman, Jr.; 1972b.
  Mild thermal degradation of pesticides.  J. Environ. Qual. 1:397-401.
Street, J. C. and R. W. Chadwick; 1967.  Stimulation of dieldrin meta-
  bolism by DDT.  Toxicol. Appl. Pharmacol. 11:68-71.
Sundaram, K. M. S.; 1974.  DDT residues may be lost from soil by direct
  volatilization.  Bi-Mon. Res. Notes, Can. Forest Serv. 30:14-15.
Sweeny, K. H., and J. R. Fischer; 1970.  Controlled self destruction of
  pesticides.  U.S. Clearinghouse Fed. Sci. Tech. Inform. PB Rep. #
  198224, 131 pp.
Sweeny, K. H., J. R. Fischer, A. F. Graefe, K. L. Marcus and D. H. W.
  Liu; 1974.  Development of field applied DDT.  U.S. N.T.I.S., PB Rep.
  #23594318 GA, 99 pp.
Swoboda, A. R., G. W. Thomas, F. B. Cady, R. VI. Baird and W. G. Knisel;
  1971.  Distribution of DDT and toxaphene in Houston black clay on
  three watersheds.  Environ. Sci. Technol. 5:141-145.
Tarrant, K. R. and J. O'G. Tatton; 1968.  Organochlorine pesticides in
  rainwater in the British Isles.  Nature 219:725-727.
Tate, K. R.; 1974.  Influence of four pesticide formulations on micro-
  bial processes in a New Zealand pasture soil.  N.Z. J. Agr. Res. 17:
  107.
Tatton, J. 0. and J. H. A. Ruzicka; 1967.  Organochlorine pesticides in
  Antartica.  Nature 215:346-348.
Tegeris, A. S., F. L. Earl, H. E. Smalley and J. M. Curtis; 1966. Meth-
  oxychlor toxicity.  Arch. Environ. Health. 13:776-787.
Terracini, B.; 1967.  Evaluation of the carcinogenicity of the chlori-
  nated hydrocarbons used as pesticides.  Tumori 53:601-618. (Chem.
  Abstr. 68:86373n, 1968).
Terracini, B., M. C. Testa, J. R. Cabral and N. Day; 1973.  The effects
  of long-term feeding of DDT to Balb/c mice.  Int. J. Cancer 11:747-
  764.
Terriere, L. C., U. Kiigemagi, A. R. Gerlach and R. L. Borovicka; 1966.
  The persistence of toxaphene in lake water and its uptake by aquatic
                                  407

-------
  plants and animals.  J.  Agr.  Food Chem.  14:66-69.
Terriere, L. C., U. Kiigemagi,  R.  Zwick and P.  Westigard;  1965.  The
  persistence of pesticides in  orchards and orchard  soils;  a twenty
  year study.  Amer. Chem. Soc.,  Div.  Water, Air Waste Chem., Preprints
  5:49-52. (Chem. Abstr. 66:54488w, 1967).
Tewari, S. N. and D. N. Chakravarty; 1970.  Pesticide effects on micro-
  bial activity in soil.  J.  Inst.  Chem.,  Calcutta.  (Chem.  Abstr. 74:
  41378a, 1971).
Thompson, A. R. , C. A. Edwards, M.  J.  Edwards and K. I. Beynon; 1970.
  Movement of dieldrin through  soils.   II. In sloping troughs and soil
  columns.  Pestic. Sci. 1:174-178.
Thorpe, E. and A. E. T. Walker;  1973.   The toxicology of dieldrin
  (HEOD).  II. Comparative long-term oral  toxicity studies  in mice with
  dieldrin, DDT, phenobarbitone,  g-BHC and y-BHC.  Food Cosmet. Toxicol.
  11:433-442.
Thurston, R.; 1953.  The effects  of some soil charactersitics on DDT
  phytotoxicity.  J. Econ. Entomol. 46:545-550.
Tomatis, L., V. Turusov, N. Day and R. T.  Charles; 1972,  The effect of
  long-term exposure to DDT on  CF-1 mice.   Int. J. Cancer 10:489-506.
Toor, H. S., K. Metha and S.  Chhina; 1973.  Toxicity of insecticides
  (commercial formulations) to  the exotic  fish, common carp Cyprinus
  aarpio aomrnn-is.   J. Res.,  Punjab Agr. Univ.  10:341-345.  (Chem.
  Abstr. 81:58983m, 1974).
Train, R.; 1975.  Notice of intent to suspend and findings  of the im-
  minent hazard posed by registrations of  pesticides containing hepta-
  chlor and chlordane.  Environmental Protection Agency.
Triolo, A. J. and J. M. Coon; 1966.  Toxicological interactions of
  chlorinated hydrocarbon and organophosphate insecticides.  J. Agr.
  Food Chem. 14:549-555.
Trudgill, P. W. and R. Widdus;  1970.  Effects of chlorinated insecti-
  cides on metabolic processes  in bacteria.  Biochem. J. 118:48-49.
                                  408

-------
Trudgill, P. W., R. Widdus and J. S. Rees; 1971.  Effects of organo-
  chlorine insecticides on bacterial growth, respiration and viability.
  J. Gen. Microbiol. 69:1-13.
Tsirkov, I.; 1969.  Effect of organochlorine insecticides, hexachloran,
  heptachlor, lindane, and dieldrin, on the activity of certain enzymes
  in soil.  Pochvozn. Agrokhim. 4:85-88.  (Chem. Abstr. 73:54981w, 1970).
Tu, C. M., J. R. W. Miles and C. R. Harris; 1968.  Soil microbial de-
  gradation of aldrin.  Life Sci. 7:311-322 (pt. 2).
Tucker, R. K. and D. G. Crabtree; 1970.  Handbook of toxicity of pesti-
  cides to wildlife.  U.S. Fish Wildl. Serv., Bur. Sport Fish Wildl.,
  Resource Publ. #84.
Turner, B. C., A. W. Taylor and W. M. Edwards; 1972.  Dieldrin and hep-
  tachlor residues in soybeans.  Agron. J. 64:237-239.
Uchiyama, M., T. Chiba and K. Noda; 1974.  Cocarcinogenic effect of DDT
  and PCS (polychlorobiphenyl)  methylcholanthrene-induced chemical
  carcinogenesis.  Bull. Environ. Contain. Toxicol. 12:687-693.
Ukeles, R.; 1962.  Growth of pure cultures of marine phytoplankton in
  the presence of toxicants.  Appl. Microbiol. 10:532-537.
Van Dijk, P. J., H. Van de Voorde and J. Delmotte; 1973.  Biodegradation
  of the insecticide DDT.  Meded. Fac. Landbouwwetensch. Rijksuniv.
  Gent. 38:751-758.  (Chem. Abstr. 81:436u, 1974).
Van Steyvoort, L., P. H. Martens and A. J. Plasman; 1968.  Residues of
  chlorinated insecticides in beets and their by-products.  Meded.
  Rijksfac. Landbouwwetensch., Gent. 33:1277-1282. (Chem. Abstr. 71:
  5973h, 1969).
Varade, P. A., and D. K. Ballal; 1969.  Effect of some common insecti-
  cides on the availability of plant nutrients in black cotton soil.
  J. Indian Soc. Soil Sci. 17:255.  (Chem. Abstr. 72:110279s, 1970).
Vashkov, V. I.; 1949.  Bactericidal properties of some aerosols used
  for insect control.  Gigiena i Sanit. 8:37-41. (Chem. Abstr. 44:
  1166e, 1950).
Veith, G. D. and G. F. Lee; 1971.  Water  chemistry of toxaphene:  role
                                  409

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  of lake sediments.  Environ. Sci. Technol. 5:230-234.
Verschuuren, H. G., R. Kroes, E. M. Dentonkelaar; 1973.  Toxicity
  studies on tetrasul. III. Short-term comparative studies in rats with
  tetrasul and structurally related acaricides.  Toxicology 1:113-123.
Vettorazzi, G.; 1975.  State of the art of the toxicological evaluation
  carried out by the joint FAO/WHO expert committee on pesticide resi-
  dues.  I. Organohalogenated pesticides used in public health and
  agriculture.  Residue Reviews 56:107-134.
Vockel, D. and F. Korte; 1974.  Beitrage zur okologischen Chemie LXXX.
  Versuche zum mikrobiellen Abbau von Dieldrin und 2,2'-I)ichlorbiphenyl.
  Chemosphere 3:177-182.
Voerman, S. and A. F. H. Besemer; 1970.  Residues of dieldrin, lindane,
  DDT and parathion in a light sandy soil after repeated application
  throughout a period of 15 years.  J. Agr. Food Chem. 18:717-719.
Voerman, S. and A. F. H. Besemer; 1975.  Persistence of dieldrin, lin-
  dane, and DDT in a light sandy soil and their uptake by grass. Bull.
  Environ. Contain. Toxicol. 13:501-505.
Voerman, S., and P. M. L. Tammes; 1969.  Adsorption and desorption of
  lindane and dieldrin by yeast.  Bull. Environ. Contain. Toxicol. 4:
  271-277.
Vollner, L. and F. Korte; 1974a.  Beitrage zur 6'kologischen Chemie
  XCL.  Radiolyse von Chlorpestiziden-I.&tfmza-Bestrahlung von Dieldrin
  in Wasser.  Chemosphere. 3:271-274.
Vollner, L. and F. Korte; 1974b.  Beitrage zur okologischen Chemie XCII,
  Radiolyse von Chlorpestiziden. II. ftzmma-Bestrahlung in Hexan, Aceton,
  und Aceton/Wasser.  Chemosphere 3:275-280.
Vollner, L., H. Parlar, W. Klein and F. Korte; 1971.  Beitrage zur oko-
  logischen Chemie. XXXI.  Photoreaktionen der Komponenten des technis-
  chen Chlordans.  Tetrahedron 27:501-509.
Von Oettingen, W. F. and N. E. Sharpless; 1946.  The toxicity and toxic
  manifestations of DDT as influenced by chemical changes in the mole-
  cule.  Relation between chemical constitution and toxicological action.
  J. Pharmacol. 88:400-413.
                                   410

-------
Wagstaff, D. J. and J. C. Street; 1971.  Antagonism of DDT storage in
  guinea pigs by dietary dieldrin.  Bull. Environ. Contain. Toxicol.
  6:273-278.
Waldron, A. C. , H. E. Kaiser, D. L. Goleman, J. R. Staubus and H. D.
  Niemczyk; 1968.  Heptachlor and heptachlor epoxide residues on fall-C
  treated alfalfa and in milk and cow tissues.  J. Agr. Food Chem. 16:
  627-631.
Walker, A. I. T., D. E. Stevenson, J. Robinson, E. Thorpe and M. Rob-
  erts; 1969.  Toxicology and pharmacodynamics of dieldrin (HEOD):
  Two year oral exposure of rats and dogs.  Toxicol. Appl. Pharmacol.
  15:345-373.
Walker, A. I. T., E. Thorpe and D. E. Stevenson; 1973.  The toxicology
  of dieldrin (HEOD).  I. Long-term oral toxicity studies in mice.
  Food Cosmet. Toxicol. 11:415-432.
Wallcave, L., S. Bronczyk and R. Gingell; 1974.  Excreted metabolites
  of 1 ,l,l-trichloro-2,2-Ms(p-chlorophenyl)ethane in the mouse and
  hamster.  J. Agr.   Food Chem. 22:904-908.
Wallace, J. B. and U. E. Brady; 1971.  Residue levels of dieldrin in
  aquatic invertebrates and effect of prolonged exposure on popula-
  tions.  Pestic. Monit. J. 5:295-300.
Walsh, G. E., T. A. Hollister and J. Forester; 1974.  Translocation of
  four organochlorine compounds by red mangrove (JRhi-zophoPcc mangle)
  seedlings.  Bull. Environ. Contam. Toxicol. 12:129-135.
Ware, G. W.; 1975.  The effects of DDT on reproduction in higher ani-
  mals.  Residue Reviews 59:119-140.
Ware, G. W. and E. E. Good; 1967.  Effect of insecticides on repro-
  duction in the laboratory mouse.  II. Mirex, telodrin and DDT.
  Toxicol. Appl. Pharmacol. 10:54-61.
Ware, G. W. and C. C. Roan; 1970.  Interactions of pesticides with
  aquatic microorganisms and plankton.  Residue Reviews 33:15-46.
Ware, G. W., W. P. Cahill and B. J. Estesen; 1975.  Volatilization of
  DDT and related materials from dry and irrigated soils.  Bull. Envi-
  ron. Contam. Toxicol. 14:88-97.
                                 411

-------
Weatherholtz, W. M., G. W. Cornnell, R. W. Young and R. E. Webb; 1967.
  Distribution of heptachlor residues in pond eco-systens in southwes-
  tern Virginia.  J. Agr. Food Chem. 15:667-670.
Wedemeyer, G. A.; 1966.  Dechlorination of DDT by Aerobaater aerogenes.
  Science 152:647.
Wedemeyer, G.; 1967.  Dechlorination of l,l,l-trichloro-2,2-bis(p-£
  chlorophenyl)ethane by Aevobaater aerogenes.   Appl. Microbiol. 15:
  569-574.
Wedemeyer, G.; 1968.  Role of intestinal microflora in the degradation
  of DDT by rainbow trout.  Life Sci. 7:219-223.
Weikel, J. H., Jr.; 1957.  The metabolism of methoxychlor (l,l,l-tri£
  chloro-2,2-bis(p-methoxyphenyl)ethane.  I. The role of the liver and
  biliary excretion in the rat.  Arch. Intern.  Pharmacodynamie 110:
  423-432.
Weil, L., K. E. Quentin and S. Jarrar; 1972.  Analysis of pesticides
  in water.  VII. Adsorption of pesticides by suspended matter. Schrif-
  tenr. Ver. Wasser-, Boden-, Lufthyg., Berlin-Dahlem 37:77-84. (Chem.
  Abstr. 79:9521j, 1973).
Weis, P. and J. S. Weis; 1974.  DDT causes changes in activity and
  schooling behavior in goldfish.  Environ. Res. 7:68-74.
Weisgerber, I., S. Detera and W. Klein; 1974a.   Beitrage zur okologis-
  chen Chemie LXXXVIII. Isolierung und Identifizierung einiger Hepta-
        14
  chlor-  C-metaboliten aus Pflanzen und Boden. Chemosphere 3:221-226.
Weisgerber, I., J. Kohli, R. Kaul, W. Klein and F. Korte; 1974b.  Fate
            14
  of aldrin-  C in maize, wheat, and soils under outdoor conditions.
  J. Agr. Food Chem. 22:609-612.
Welch, R. M., W. Levin and A. H. Conney; 1969a.  Estrogenic activity
  of DDT and its analogs.  Toxicol. Appl. Pharmacol. 14:358-367.
Welch, R. M., W. Levin and A. H. Conney; 1969b.  in: Chemioal Fallout^
  390-407; M. W. Miller, ed.; C. C. Thomas, Springfield, 111.  Effect
  of chlorinated insecticides on steroid metabolism.
                                  412

-------
Welch, R. M. , W. Levin, R. Kuntzman, M. Jacobson and A. H. Conney; 1971,
  Effect of halogenated hydrocarbon insecticides on the metabolism and
  uterotropic action of estrogens in rats and mice.  Toxicol. Appl.
  Pharmacol. 19:234-246.
Wells, D. M., E. W. Huddleston and R. G. Rekers; 1970.  Potential pol-
  lution of the Ogallala by recharging playa lake water pesticides.
  U.S. Nat. Tech. Inform. Serv., PB Rep #208813, 1970, 40 pp.
Whaley, H., G. K. Lee, R. K. Jeffrey and E. R. Mitchell; 1970.  Ther-
  mal destruction of DDT in an oil carrier.  Can., Mines Br., Res. Rep.
  R. 225, 36 pp. (Chem. Abstr. 73:101781t, 1970).
Wheatley, G.; 1973.  in: Environmental Pollution by Pesticides.  C. A.
  Edwards, ed.; Plenum Press, London, N. Y.; Pesticides in the atmos-
  phere.
Wheatley, G. A. and J. A. Hardman; 1965.  Indications of the presence
  of organochlorine insecticides in rainwater i.i central England.
  Nature 207:486-487.
Wheeler, W. B., D.  E. H. Frear, R. 0. Mumma, R. H. Hamilton and D. C.
  Cotner; 1967.  Absorption and translocation of dieldrin by forage
  crops.  J. Agr. Food Chem. 15:231-234.
Wiese, I. H.; 1964.  Biological studies on the inactivation of insec-
  ticides by various soil types.  S. African J. Agr. Sci. 7:823-835.
  (Chem. Abstr. 63:15479e, 1965).
Wilkinson, A. T. S., D. G. Finlayson and H. V. Morley; 1964.  Toxic
  residues in soil nine years after treatment with aldrin and hepta-
  chlor.  Science 143:681-682.
Williams, C. H., J. L. Casterline, Jr., K. H. Jacobson and J. E. Keys;
  1967.  Studies of toxicity and enzyme activity resulting from inter-
  action between chlorinated hydrocarbon and carbamate insecticides.
  Toxicol. Appl. Pharmacol. 11:302-307.
Willis, G. H. and R. A. Hamilton; 1973.  Agricultural chemicals in sur-
  face runoff, ground water, and soil:  1. Endrin.  J. Environ. Qual.
  2:463-466.
                                  413

-------
Willis, G. H., J. F. Parr and S. Smith, Jr.; 1971.  Volatilization of
  soil-applied DDT and DDD from flooded and non-flooded plots. Pestic.
  Monit. J. 4:204-208.
Willis, G. H., J. F. Parr, S. Smith and B. R. Carroll; 1972.  Volati-
  lization of dieldrin from fallow soil as affected by different soil
  water regimes.  J. Environ. Qual. 1:193-196.
Wilson, D. M. and P. C. Oloffs; 1974.  Residues in plants grown in
  soils treated with the experimental insecticide Velsicol HCS-3260.
  Can. J. Plant Sci. 54:203-209.
Wilson, J. K. and R. S. Choudhri; 1946.  Effects of DDT on certain
  microbiological processes in soil.  J. Econ. Entomol. 39:537-538.
Winely, C. L. and C. L. SanClemente; 1970.  Effects of pesticides on
  nitrite oxidation by Nitrobaetep agi-li-s,  Appl. Microbiol. 19:214-
  219.
Wingo, C. W.; 1966.  Persistence and degradation of dieldrin and hepta-
  chlor in soil and effects on plants.  Mo., Univ., Agr. Exp. Sta.,
  Res. Bull. #914, 27 pp. (Chem. Abstr. 66:94202e, 1967).
Wolcott, G. N.; 1954.  Residual effectiveness of insecticides against
  soil-inhabiting insects.  J. Agric. Puerto Rico 38:108-114.
Woods, R. J. and S. Akhtar; 1974.  Radiation-induced dechlorination of
  chloral hydrate and l,l,l-trichloro-2,2-bis(p-chlorphenyl)ethane
  (DDT).  J. Agr.   Food Chem. 22:1132-1133.
Woodward, G., R. R. Ofner and C. M. Montgomery; 1945.  Accumulation of
  DDT in the body fat and its appearance in the milk of dogs.  Science
  102:177-178.
Woodwell, G. M., C. F. Wurster, Jr. and D. A. Isaacson; 1967.  DDT
  residues in an east coast estuary:  a case of biological concentra-
  tion of a persistent pesticide.  Science 156:821-824.
Wurster, C. F.; 1971.  Aldrin and dieldrin.  Environment 13(8):33-45.
Wuu, K. D. and W. F. Grant; 1966.  Morphological and somatic chromoso-
  mal aberrations induce^ oy pesticides in barley (EOTdeum Vulgare).
  Can. J. Genet. Cytol. 8:481-501.
                                  414

-------
Yamamoto, R. S., J. H. Weisburger and E. K. Weisburger; 1971.  Control-
  ling factors in urethan carcinogenens in mice.  Effect of enzyme in-
  ducers and metabolic inhibitors.  Cancer Res. 31:483-486.
Yaron, B., A. R. Swoboda and G. W. Thomas; 1967.  Aldrin adsorption by
  soils and clays.  J. Agr. Food Chem. 15:671-675.
Young, R. W. ; 1969.  Residues of dieldrin and DDT in peanuts and turnip
  greens grown in soil containing these compounds.  Pestic. Monit. J.
  3:94.
Young, L. A. and H. P. Nicholson; 1951.  Stream pollution resulting
  from the use of organic insecticides.  Progr. Fish-Cult. 13:193-198.
Yule, W. N., M. Chiba and H. V. Morley; 1967.  Fate of insecticide
  residues.  Decomposition of lindane in soil.  J. Agr. Food Chem. 15:
  1000-1004.
Zatz, J. L.; 1972.  Accumulation of organochlorine pesticides in man.
  J. Pharm. Sci. 61:948-949.
Zimmer, M. and W. Klein; 1972.  Beitrage zur bkologischen Chemie-XXXVII.
                                                   14
  Riickstands-verhalten und Umwandlung von p_,p'-DDT-  C und seiner Ana-
                  14               14
  logen, p3p '-DDE-  C und p^p'-DDD-  C in hb'heren Pflanzen.  Chemos-
  phere 1:3-6.
Zoro, J. A., J. M. Hunter, G. Eglinton and G. C. Ware; 1974.  Degra-
  dation of p,p '-DDT in reducing environments.  Nature 247:235-236.
Zweig, G., E.  L. Pye, R. Sitlani and S. A. Peoples; 1963.  Residues in
  milk from dairy cows fed low levels of toxaphene in their daily ra-
  tion.  J. Agr. Food Chem. 11:70.
                                  415

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ORGANOPHOSPHORUS INSECTICIDES
Methyl Parathion and Parathion
Methyl parathion is the common name for 030-d±methyl C>-p-nitrophenyl
phosphorothioate, known as parathion-methyl in western Europe and as
metaphos in the USSR.  Introduced in 1949 by Farbenfabriken Bayer as
"Dalf" or "Folidol-M1, methyl parathion is a nonsystemic contact and
stomach insecticide.  When pure, it is a white crystalline powder with
a melting point of 35  to 36 C and a vapor pressure of 0.97 x 10  mm
mercury at 20 C.  At 25 C its solubility in water is 55 to 60 ppm; it
is slightly soluble in light petroleum and mineral oils and soluble in
most other organic solvents.  The technical product is a light to dark
tan liquid of about 80 percent purity (Martin 1968).
Parathion is the common name for (9,£>-diethyl 0-p-nitrophenyl phosphoro-
thioate, also a nonsystemic contact and stomach insecticide.  Known as
thiophos in the USSR, parathion is a pale yellow liquid with a boiling
point of 157 C at 0.6 mm mercury, and a vapor pressure of 3.78 x 10  mm
mercury at 20 C.  Its solubility in water is 24 ppm at 2.5 C, and it is
slightly soluble in petroleum oils.  It is miscible with most organic
solvents.  Parathion can be hydrolyzed in alkaline media, but only one
percent is hydrolyzed in 62 days at pH five or six (Martin 1968) .
Parathion is synthesized by condensing diethyl phosphorochloridothioate
with sodium p-nitrophenate, while methyl parathion requires dimethyl
phosphorochlorodithioate.
Degradation-
Biological—Biological pathways of parathion degradation are shown in
Figure 16; pathways for methyl parathion are analogous.  The metabolic
products of microbial degradation of methyl parathion are listed in
Table 59, as are data representative of mammalian degradation/metabolism.
                                   416

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                            HO-

                                P—OH
                          C2H50
           NO 2


P-NITROPHENOL
                            ANIMAL
                                              HO.
                                           C2H50
                                                              MO-
                                      —OH
                                                         T
                                                         ANIMAL
(C2H50)2P-0  Q
 (C2H50)2P-0/Q
                                                         NO,
                                                      PARAOXON
          PARATHIOH

               r~
            FISH
          MICROBES
                                                        FISH

                                                      MICROPES
(C2H50)2P-0/Q



   AMINOPARATHION
(r.2H5o)2  o- I
                                                 0
                                                 II
                                         (C,HcO),D_ OH
                                                         MH,
                                                  CONJUPATE
         DEGRADATION  PATHWAYS FOR PARATHION (MODIFIED

          HAQUE  AND FREED 1075),  DEGRADATION °ATHWAYS FOR

                  METHYL PARATHION ARE ANALOGOUS,
                        Figure 16
                             417

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The microbial degradation of parathion has been documented repeatedly
(Singh 1974, Boush and Matsumura 1967, Griffiths and Walker 1970, Get-
zin and Rosefield 1968) .  Table 60 lists specific organisms and the
products of their degradation.
Naumann (1959) observed that methyl parathion was 99.9 percent degra-
ded in three weeks if 0.5 to one percent (5,000 to 10,000 ppm) were
added to the soil.  Sterilized soil had first to be recolonized before
degradation took place.  Sethunathan  (1973a, 1973b) and Sethunathan and
Yoshida (1973a, 1973b) found that parathion was degraded more rapidly
in flooded soil or under anaerobic conditions than under aerobic con-
ditions.  If flooded soil was additionally inoculated with Flavohac-
teTium,, the half-life of parathion was approximately 0.76 days, com-
pared to 3.5 days in uninoculated soil.  Aminoparathion was the pri-
mary anaerobic metabolite, with p-nitrophenol as the terminal residue.
Baci-llus species were found which were capable of degrading p-nitro-
phenol to carbon dioxide.  Maximum initial degradation of parathion
occurred in acid sulfate soil under anaerobic conditions and repeated
applications enhanced the degradation in alluvial soils.  Ring clea-
vage and CO- production, however, occurred only under aerobic condi-
tions .
Penicillium waksmani degraded up to 1000 mg/ml (1000 ppm) parathion on
agar, but was inhibited at higher levels of parathion.  After 15 days,
61 percent of the parathion had been degraded, with aminoparathion as
the major product (Rao and Sethunathan 1974).  The addition of organic
natter shifted degradation from the hydrolytic pathways typical of
aerobic unflooded soils to reductive pathways, increasing production
of aminoparathion (Rajaram and Sethunathan 1975) .  A mixed bacterial
culture degraded a parathion-xylene formulation in aqueous medium at a
maximum rate of 50 mg/liter/hour, or with an optimum parathion concen-
tration of 5000 mg/liter (5°00 ppm) in batch cultures.  Both the xylene
diluent and the parathion were metabolized,  the latter preferentially
                                  419

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at slightly alkaline pH.  Complete air saturation, a pH between 7.0
and 7.5, a temperature of 37 C were optimal.  Five of six pseudomo-
nads isolated from the mixed culture used an ortho ring fission system
for p-nitrophenol metabolism while the sixth did not grow on p-nitro-
phenol  (Munnecke and Hsieh 1975).
Naumann (1967) found a Pseudomonas species which was able to dissolve
crystalline methyl parathion from the medium in four to eight weeks.
Siddaramappa et al. (1973) found that Pseudomonas could degrade para-
thion (formulated as Folidol) in a 1,000 ppm aqueous solution with 20
grams of alluvial soil and 24 ml water; two weeks were required for the
degradation.  In sewage lagoons, parathion was degraded less rapidly
than malathion but more rapidly than diazinon (Halvorson et al. 1971),
and both parathion and methyl parathion were inactivated within days
by polluted stream water (Yasuno et al. 1966).  Bacillus subtilis was
highly effective in converting parathion to aminoparathion and methyl
parathion to methylaminoparathion (ibid).
In summary, both parathion and methyl parathion appear to be eminently
degradable compounds in that microorganisms capable of degrading them
exist.  Since both compounds appear to serve as energy sources for the
degrading microorganisms, selection for more efficient degradation is
plausible, in contrast to the situation found for cometabolism by or-
ganochlorine-degrading microorganisms (Alexander 1972).
On plants, evaporation and photolysis predominated as modes of para-
thion removal (Popov and Khol'kin 1958).  Paraoxon decomposed more
rapidly than parathion on citrus foliage (Spear et al. 1975).  The ma-
jor metabolites of methyl parathion in rice grains were thiophosphoric
acid and 0,0-dimethyl thiophosphoric acid (Tomizawa et al. 1962).
Parathion is rapidly metabolized in mammals.  In rabbits, the maximum
blood levels were found twenty minutes after intravenous injection of
six to ten mg/kg parathion, and removal from the blood occurred in 30
                                 421

-------
to 60 minutes.  A second injection was cleared less rapidly (Gar et al.
                                   32
1955).  In rats, maximum levels of   P were found in liver, brain,
lungs, and kidneys within two hours after ingestion; bone levels of
32
  P increased for only seventy-two hours (Kortus et al. 1968).
Hollingworth et^ al_. (1967a, 1967b) compared the metabolism of methyl
parathion with the less toxic fenitrothion 0,0-dimethyl 0-(3-methyl-
4-nitrophenyl) phosphorothioate.  Analysis of urinary and fecal meta-
bolites of the two compounds in mice demonstrated that direct excre-
tion of their oxygen analogs was a significant detoxification mecha-
nism.  The parent compounds were not, however, excreted directly.  Nei-
ther ring hydroxylation nor reduction of the nitro group to the amino
group were significant in mice.  As dosage increased, the excretion of
dimethyl phosphoric acid did not rise proportionally, whereas the lev-
els of desmethyl phosphorothionate increased from a secondary metabo-
lite to the major urinary metabolite.  It was concluded that, whereas
hydrolytic removal of dimethyl phosphoric acid was the primary murine
detoxification mechanism, desmethylation was a secondary route availa-
ble when levels of the toxicants became too high and the hydrolyzing
enzyme systems were overwhelmed.
In rat liver slices, parathion activation to paraoxon was associated
with the microsomal or mitochondrial fraction (Nakatsugawa and Dahm
1967, Fukami and Shishido 1963).  In female rats, 4.4 percent of the
LD-,. dose was converted to paraoxon within one hour, with 64 percent
of the conversion occurring in the liver (Kubistova 1959) .  In dairy
cows, 14 ppm for 61 days produced no detectable parathion in milk,
blood, or urine of the cattle; conjugation with a p-aminoglucuronide
prior to urinary excretion was postulated (Pankaskie et al. 1952).
Gyrisco and his co-workers (1959) found no residues in the milk of four
dary cows fed ten ppm of parathion for three years.  In sheep, how-
ever, 0.10 to 0.15 percent of a daily ingested dose of 2.0 to 5.5 mg/kg
was excreted in the milk; four to five mg/kg parathion also decreased
the volume of milk produced (Alamanni and Cossedu 1969) .
                                  422

-------
                                                      o
Photolytic—Ultraviolet light between 1,850 and 4,000 A  converts para-
thion to paraoxon  (Payton 1953).  On leaf surfaces and glass, sunlight
catalyzed the conversion of parathion to paraoxon  (about one percent)
and to p-nitrophenol  (El-Refai and Hopkins 1966).  Parathion in ethanol
is photolyzed to C^S-triethyl thiophosphate as a major product, and
paraoxon and 030S(9-triethyl phosphate as minor products (Grunwell and
Erickson 1973).  Koivistoinen and Meilainen (1962a, 1962b) claimed that
paraoxon was not affected by ultraviolet light.  Baker and Applegate
(1970) examined the effects of temperature and ultraviolet light on
methyl parathion and  found that UV radiation increased removal of methyl
paration from soils by ten to 14 percent at 30 C and by 14 to 17 per-
cent at 50°C.
Chemical and physical—Parathion is most readily degraded by hydrolysis,
which is easily catalyzed by peroxidases or by ferrous iron and EDTA
(ethylenediaminetetraacetic acid) (Knaak et al. 1962).  In natural a-
queous medium approximately 70 percent of the parathion was hydrolyzed
in four weeks and 72  percent in six weeks.  In another study, 74 per-
cent of the methyl parathion was hydrolyzed in six weeks (Cowart et al.
1971).  Hydrolytic degradation eventually proceeded to the terminal
residue p-nitrophenol, itself toxic.
Hydrolysis of parathion proceeded more rapidly in calcareous sediment
than in slightly acid sediments; aminoparathion was the major metabo-
lite (Graetz et_ a!L. 1970).  At a pH of 7.4 at 20°C, parathion was es-
timated to have a half-life of 108 days if chemical hydrolysis were the
means of degradation; under the same conditions, paraoxon had a half-
life of 114 days (Faust and Gomaa 1972).  In bottled river water both
methyl parathion and  parathion were completely degraded within eight
weeks (Eichelberger and Lichtenberg 1971).  Menzie (1972)  considered
parathion to be nonpersistent in water.
Under shelf storage,  less than four percent of a 50 percent methyl
parathion emulsion decomposed in sixteen months (Raman and Krishna-
                                   423

-------
moorthy 1973).  Dust formulations of methyl parathion decomposed to
give i9,0-dimethylphosphate, its ^-methyl isomer, (9-methyl 5-methyl
0-p-nitrophenylthiophosphate and p-nitrophenol  (Gota et_ al. 1960).
Parathion could be removed from noncombustible containers by washing,
and disappeared from 50 percent ethanol washes within five hours.  So-
dium hydroxide and sodium hypochlorite were less effective (Hsieh jet
al. 1974).
Parathion can be converted to paraoxon by seven percent chlorination
of water or by one to two ppm of ozone, but potassium permanganate at
ten to 40 ppm was not effective (Robeck &t_ al. 1965).  The toxic de-
gradation product p-nitrophenol, if present to one part per hundred in
water, could be removed by the addition of 40 kilograms of sodium hy-
droxide plus 50 kilograms of bleaching powder for each 200 liters of
water:  after two to three hours at 100 C, all organic compounds were
removed from the water and 320 grams of inorganic salts were produced
per liter of water (Mel'nikov et al. 1958).
Radiolysis was successfully used to degrade parathion:  0.1 to 5.0 Mrads
resulted in 27 percent degradation of parathion in hexane solution
(Lippold et al. 1969) and 10,000 rads of jyomma-radiation from a   Co
source resulted in better than 80 percent destruction of sufficiently
dilute aqueous solutions (Sunada 1967).  Sufficiently dilute was de-
fined as concentrations measured in parts per trillion.
Transport-
Within soil—McCarty and King (1966) stated that methyl parathion and
parathion migrated rapidly in soil-water systems, but were also de-
graded rapidly.  Lichtenstein et_ al. (1967) found, on the contrary,
that parathion moved through soil less rapidly than aldrin.  Some para-
thion entered water through sorption to loam and transport with loam
particles, and one ppm of parathion in the presence of percolating
water resulted in small water residues of the pesticide.  In soil col-
umns of Nacodoches clay subsoil, parathion leached to 60 inches when
                                   424

-------
230 inches of rainfall were simulated, while in Houston black clay,
1,725 inches of simulated rain were required to produce leaching to
60 inches (Swoboda and Thomas 1968).  Adsorption was found to be the
main factor retarding mobility, and Swoboda and Thomas (1968) consid-
ered parathion to be dissolving as a liquid phase in an organic frac-
tion of the soil.  Parathion applied at 0.1 pounds per acre, followed
by flooding and a subsequent application of 0.2 pounds per acre, was
degraded before reaching drainage tiles six feet below the soil sur-
face (Johnson et al. 1967).
Stewart &t_ al. (1971) reported that little leaching occurred in six-
teen years after four annual applications of 31.4 pounds of parathion,
despite 42 inches of precipitation per year.  Wolfe et al. (1973) re-
ported that very little parathion was found below the nine inch level
six years after 30,000 to 95,000 ppm of parathion were applied to soil.
In a 15 year study of pesticide residues in light sandy soil, Voerman
and Besemer found that dieldrin and DDT, but not lindane or parathion,
leached to 60 centimeters; parathion was not found below 20 centime-
ters.  Mol et^ sil_. (1972) did not find parathion much below 2.5 centi-
meters even with 220 mm of rain during the eight month persistence of
parathion under their experimental conditions.  Burkhardt and Fairchild
(1967) applied parathion (formulated as Niran) in several sandy soils,
and observed increased mobility at higher levels of moisture.  Sacher
and co-workers (1972) observed little movement of parathion in char-
coal or kaolinite formulations.  Parathion contamination of a farm
pond and its sediment was correlated with the degree of erosion, sug-
gesting that parathion moved with soil particles rather than by leach-
ing (Nicholson et_ al. 1962) .
No mention is made in these studies of the fate or mobility of the de-
gradation products of parathion or methyl parathion.
Between soil and water—When soil was added to parathion in water, 63
percent of the parathion was adsorbed by the soil from a low volume of
                                  425

-------
water (100 ml), but only 38 percent was adsorbed from a larger volume
(250 ml).  The carrier, the depth of the water, its agitation, and the
rate of parathion application all affected the rate of loss of para-
thion to soil (Weidhass et_ al. 1961).  King et_ al. (1969) tested the
ability of several adsorbents to remove parathion from water, and
found that soil with a high clay content was more effective than sandy
soil; coal was 2.5 times as effective as soil, and algal systems were
ten times as effective as soil.  Activated charcoal had 1,000 times the
sorptive capacity of soil.  Movement of parathion into water from soil
appeared to occur by erosion rather than by leaching (Nicholson et_ al.
1962).
Into organisms—The high toxicity of parathion and methyl parathion in
most animals makes bioaccumulation unlikely, nor has evidence for it
been found in cattle (Pankaskie et_ al^. 1952, Gyrisco et_ al_. 1959),
sheep (Alamanni and Cossedu 1969) or rabbits (Kortus et al. 1968).
Methyl parathion was taken up by carrots from soil and retained for up
to four weeks (Engst et_ al_. 1966a, 1966b) .  No methyl paraoxon was
found, suggesting very slow metabolism (1966a) but five phosphorus-^
containing degradation products were found, including monomethyl phos-
phate and dimethyl phosphate  (1966b).  El-Refai and Hopkins (1966)
documented the transfer of ten percent of foliar applications of para-
thion into the bean plant.  Smith (1950) said that only minute amounts
of the parathion absorbed from foliar applications was translocated
within the plant, and Zuckerman et_ al. (1966) did not find any trans-
fer to roots or soil from foliar applications, but near-insecticidal
levels of parathion were transported from soil to leaves.
Bean plants grown in soil containing parathion contained parathion met-
abolites if and only if microorganisms capable of metabolizing para-
thion were present in the soil; in sterile root cultures, bean plants
translocated only unaltered parathion (Mackiewicz et al. 1969).
                                  426

-------
Studies of parathion movement in a model cranberry bog demonstrated
that both fish and microorganisms are capable of accumulating parathion;
fish metabolized the compound better than did mussels, and dead fish
accumulated 80-fold the water concentrations of parathion (Miller et
al. 1966).
In the terrestrial-aquatic model ecosystem only fish contained para-
thion (0.1006 ppm) at the end of the 38 day experiment and none of the
ecosystem organisms contained paraoxon.  Most of the organisms con-
tained radioactivity; 68 percent of the radioactivity in the algae,
Daphniaj snails, and mosquito larvae was unextractable; in the fish,
only 19.7 percent was unextractable, although only 31.5 percent of the
unextractable material (6.21 percent of the total piscine radioactivity)
was parathion (Yu and Sanborn 1975).  Parathion, paraoxon, and p-nitro-
phenol were found in the water at 0.3, 0.47, and 1.4 ppb, respectively.
Parathion was estimated to have a half-life of 15 to 16 days in water,
and no evidence was found for bioaccumulation in any of the organisms
(Yu and Sanborn 1975, Metcalf and Sanborn 1975).
Volatilization-
On petri dishes, parathion in ethanol solution at 35 C was 62 percent
volatilized in 90 days (Allessandri and Amormino 1954) while 94 per-
cent of parathion sprayed on peach leaves was lost within one week
(Brunson and Koblitsky 1952).  Mistric and Gaines (1953) found that
wind, sun, and rain, and/or high temperatures significantly increased
the volatilization of methyl parathion and parathion, which, if pro-
tected from these elements, retained their full insecticidal power for
more than 24 hours, and for more than 48 hours, respectively.  After
one pound per acre of methyl parathion or parathion was sprayed on
cotton in Arizona, immediate residues were 106 ppm of methyl parathion
and 117 ppm of parathion; after 96 hours, residues had fallen to 3.9
and 5.5 ppm, respectively (Ware et_ al^. 1972).
                                  427

-------
Polizu and Floru (1967) observed maximum volatilization of parathion
at a relative humidity of 40 percent and a temperature between 20 and
50 C; the precise emulsifiers present did not seem to affect the rate
of volatilization.  Quinby and co-workers (1958) estimated a half-life
of less than 0.5 hours for methyl parathion on cotton in Mississippi,
where these conditions for maximum volatilization probably held.  Para-
thion was also lost more rapidly at high temperatures (Mistric and Mar-
tin 1956).  Encapsulated parathion persisted for up to 70 days on peach
foliage, however (Winterlin e_t_ Q. 1975).
Although the studies cited did not distinguish between volatilization
and photolysis, the importance of volatilization or of dust-borne
transport is emphasized by the presence of organophosphate pesticides
in the atmosphere above the southeastern United States (Stanly et^ ajU
1971).
Persistence-
Data on the persistence of parathion, methyl parathion and parathion
metabolites are summarized in Tables 61 and 62 for those studies in
which the percent of residue remaining after a specified time could be
ascertained.  At ordinary levels of application, either to soil or to
foliage, both compounds are degraded within weeks if microbial degra-
dation can occur (Lichtenstein et_ al. 1968), and accumulation even of
repeated doses is unlikely (Goldsworthy and Foster 1950).  Under con-
ditions of excessive application or incorporation to the soil, however,
the ordinary modes of degradation do not appear to function.  Simula-
ted spills of concentrated parathion resulted in 15 percent residues
after five years (Wolfe e_t_ al_. 1973) and 0.1 percent after 16 years
(Stewart et_ al. 1971).  The residue levels of 13,800 ppm reported by
Wolfe e_t^ al. (1973) were considered high enough to be lethal and were
considered a plausible contamination arising from normal methods of
transferring parathion.  Microorganisms in the area of the simulated
spill did not show adaptation in degrading parathion or enhanced re-
                                  428

-------





















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sistance to parathion and the number of bacterial colonies in the vi-
cinity was reduced.  A similar observation was made by Kasting and
Woodward (1951) who observed that 2 lb/A (2.24 kg/ha) of soil-applied
parathion disappeared within 16 days, whereas 100 Ibs/A (112 kg/ha)
persisted for over 165 days.
Methyl parathion was also said to be retained longer in the soil if the
initial concentration was substantial (Naishtein et^ al. 1973); the
authors did not consider soil microorganisms to be the primary means of
degradation.  Stobwasser (1963) observed that the second year's appli-
cation of parathion produced lower residues in carrots, even though
higher levels were applied, than did the first year's treatment.
Persistence of parathion and methyl parathion were found to depend on
the type of soil and the rate of application (Burkhardt and Fairchild
1967).  In the laboratory, at 30 C and 40 percent soil moisture, three
ppm of parathion remained in Windy loam eight months after 20 ppm had
been incorporated.  Under the same conditions, Mocho silt loam, Linne
clay, and Madera sandy loam retained one to two ppm after 30 days, and
Laveen loamy sand retained only 0.2 ppm after 30 days.  Changing the
moisture resulted in persistence of up to 1.5 ppm in silt loam after
eight months instead of after one month.  Both microbial and hydrolytic
degradation were considered to contribute to the dissipation of the
parathion (Iwata et al. 1973).
Harris and Mazurek (1966) compared the activity of pesticides in dry
mineral soil, moist mineral soil and muck.  Both parathion and methyl
parathion were most effective in moist mineral soil and least effec-
tive in dry sand or clay, but more effective in moist muck (Harris
1966).  When clay was added to sandy loam, the effectiveness of para-
thion decreased (Harris 1967).  Liang and Lichtenstein (1974) compared
the toxicity of parathion to fruit flies on sand and on silt loam and
observed greater toxicity on sand; parathion toxicity synergized with
atrazine if the latter was present at levels of at least 19 ppm.  In
                                  432
-------
sandy loam, parathion lost its effectiveness within four weeks (Harris
1969).  The addition of detergents increased the two month persistence
level of parathion thirteen-fold and the detergents also synergized the
toxicity of the pesticide against fruit flies (Lichtenstein 1966).
Leenheer and Ahlrichs (1971) analyzed the kinetics of parathion adsorp-
tion on soil organic matter and determined that the initial rate of
adsorption was limited by the diffusion of the pesticide onto the ad-
sorptive sites on the outer surfaces of the adsorbent; after about ten
minutes, the limiting factor became the diffusion of parathion into
the interior of the adsorbent.  The fast, reversible adsorption, with
low heats of adsorption and high adsorptive capacity on hydrophobic
surfaces which was characteristic of parathion was considered indica-
tive of physical adsorption, with Van der Waals bonds between parathion
and the adsorbent surfaces (Leenheer and Ahlrichs 1971).  Yaron and
Saltzman (1972) suggested that parathion cannot displace the strongly
adsorbed water molecules in partially hydrated systems, so adsorption
occurs mainly on water-free surfaces.  In consequence, parathion toxi-
city in clay or organic soil increases, and its persistence decreases,
as increasing soil moisture prevents its adsorption (Naumann 1959,
Harris 1964a, Harris 1964b, Lichtenstein and Schulz 1964, Harris and
Mazurek 1966, Harris 1967, Chopra and Khullar 1971).  Increasing a-
mounts of clay or organic matter also provided more hydrophobic sites
on which parathion could be adsorbed (Chopra et^ al. 1970, Saltzman et_
al. 1972).
Parathion was more readily adsorbed on organic than on mineral surfaces
from aqueous solution, and bonding to organic matter was stronger.  De-
sorption from mineral surfaces was rapid and essentially complete, but
only small amounts of parathion were released from organic matter
(Saltzman et_ al_. 1972, Kliger and Yaron 1975).  Hot only did organic
matter adsorb more parathion than did clays, but sodium montmorillon-
ite was a better adsorbent than was kaolinite (Saltzman and Yaron 1972).
                                  433
-------
Additltion of organic matter was also found to alter the route of para-
thion degradation from hydrolysis to nitroreducation, with aminopara-
thion as the product (Sethunathan 1973).
The persistence of parathion was said to be increased by increasing
the pH (Carlo et al. 1952) or decreasing the temperature (Chopra and
Khullar 1971, Yaron and Saltzman 1972, Baker and Applegate 1970).
Methyl parathion added to sandy-clayey soil at 20 mg/kg decomposed in
seven days at 20 to 25 C when the soil moisture was 6.5 to 10 percent,
but in ten to eleven days when the soil moisture was reduced to 1.7
to 3.4 percent (Obuchowska 1967).  Emendation of soil with different
ions altered adsorption and the relative magnitude of adsorption in
                                _i_     I  I     i I      _i_
the presence of the ions was:  H  > Ca   > Mg   > Na  (Chopra et al.
1970).
The persistence of methyl parathion was twice as great in ultra-low-
volume sprays as in emulsifiable concentrations when sprayed on fol-
iage in normal agricultural usage (Saini et^ al_.  1970).  In dusts, in-
creasing the mean particle size of the carrier from 11.8 microns to
23.2 microns speeded degradation by about five percent (Takehara et aj^
1967a).  Methyl parathion was more rapidly degraded from a Zeeklite
formulation than from clay L; the rate of degradation varied directly
with the total iron content, the amorphous mineral content, and the
base exchange capacity of the formulation (Takehara et al_. 1967b).
Effects on Non-Target Species-
Microorganisms—The effect of parathion and methyl parathion on soil
microorganisms are summarized in Tables 63 and 64 and Table 65, re-
spectively.  The few data on analogs and metabolites are also included
in Table 65.
Capriotti and Martini (1959) found parathion to inhibit the growth of
microflora at normal levels of application, but Somer (1970) observed
no such inhibition.  Cowley and Lichtenstein (1970) observed fungal
                                   434
-------










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inhibition at levels approximating field applications of parathion and
of the seventeen fungi tested, none was able to use parathion as a
source of carbon or phosphorus.  Since the data were obtained under
laboratory conditions, the authors warned against extrapolation to
field conditions.  Parathion was tested for mutagenicity in Esaher'ic'h.'ia
Goli K-12 and was not mutagenic (Mohn 1973), but did inhibit aflatoxin
synthesis by Aspergillus (Hsieh 1973).
The effects of methyl parathion on soil microorganisms have been thor-
oughly investigated by Naumann (1970a, 1970b, 1970c, 1970d, 1971), as
summarized in Table 65.  Naumann noted that nitrogen-fixing bacteria
were most affected by methyl parathion (formulated as Wofatox), where-
as denitrifying bacteria and soil algae tended to remain unaffected.
Bacterial populations tended to increase and fungal populations to de-
crease (1970b).  When soil respiration was measured in a Warburg appa-
ratus, 500 ppm or less of methyl parathion resulted in a decrease in
soil respiration, followed several hours later by an increase; three
separate additions of 5,000 ppm ended the respiratory stimulation after
12 weeks.  The effects were similar in clay, sand, or compost, but were
least marked in clay.  Formulated methyl parathion, in contrast to the
pure compound, depressed actinomycetes, nitrogen-fixing bacteria, cell-
ulolytic bacteria, denitrifying bacteria, and soil algae (I970d).  The
data make it very clear that methyl parathion served as a substrate for
soil microorganisms (1970c).  Mohn (1973) considered methyl parathion
a probable mutagen after testing it in E. soli.
Despite the melange of techniques, it would appear that parathion and
methyl parathion stimulated the soil microflora, particularly bacteria.
The source of such stimulation is those organisms which, using para-
thion or methyl parathion as energy sources, multiply in their presence.
Since only a small proportion of the total soil microflora, and even
of the species known to degrade these pesticides, could be expected to
have the actual capability of using parathion as an energy source, the
                                  438
-------
inhibition of pure cultures by parathion is not inconsistent with over-
all stimulation of soil respiration.
When algae (Anaoystus nidulans, Scenedesmus obliquus) and protozoa  (Eu-
glena gracilis, Pavcaneciwn bwpsaria, Paramecizm rnultimicronucleatim)
were exposed to parathion at one ppm for seven days, neither adverse
effects nor any metabolites were found, although parathion was concen-
trated from 50 to 116-fold (Gregory £t_ sd. 1969).  Cabejszek and Mal-
eszevska (1970) found that 0.16 to 0.80 mg/liter (0.16 to 0.80 ppm)
of methyl parathion decreased oxygen consumption by aquatic organisms
within 30 minutes, but Luczak and Maleszevska (1966) observed no in-
hibitory effect from methyl parathion formulated as Wofatox at ten
mg/liter (10 ppm), and observed stimulation of nitrate-reducing bac-
teria at 250 mg/liter (250 ppm).
Plants—Parathion and methyl parathion are not considered to be phyto-
toxic (Martin 1968).  At two Ibs/A (2.24 kg/ha), however, parathion
decreased the stands of cucumbers, bush beans, and turnips, and reduced
the quality of peas, cauliflower, and Swiss chard (Stitt and Evanson
1949).  Sprays were less damaging than root drenches (Dennis and Ed-
wards 1963).  In quartz sand at 30 ppm (equivalent to 16.8 kg/ha) para-
thion increased the respiration of corn root tips (Lichtenstein et al.
1962) .  Leaf damage to sorghum was reported from both parathion and
methyl parathion  (Meisch et^ al_. 1970).  Parathion did not, however,
accumulate in carrots under conditions producing residues of diazinon
and other organophosphates (Bro-Rasmussen et al. 1969) .  Anaphase in-
hibition was caused by 0.0001 to 0.05 percent solutions of parathion
in the onion, Alli-im aepa; c-mitoses, chromosome and chromatid breaks,
micronuclei and anaphase bridges were also observed (Ravindran 1971).
Invertebrates—Methyl parathion at ten ppt killed 80 percent of Louis-
iana red crayfish (Procambarus clarkii) within five days in the labor-
atory, but 100 ppb had no effect in the field (Hendrick et_ al_. 1966).
                                   439
-------
Aquatic invertebrates were killed by levels of parathion ranging from
0.004 ppm in the caddis fly (Aratopsyahe gvandis) to 0.032 ppm in the
stone fly (Pteromareys ealifornicd); only endrin was consistently more
toxic (Gauf in et^ ^. 1961, 1965).  Luedemann and Neumann (1962) point-
ed out that, although the organophosphates were less toxic to fish
than the organochlorines, both classes were equally toxic to piscine
food organisms.
The effects of organophosphates on soil invertebrates have been treated
in the excellent review of Edwards (1973) who concluded that, although
not as toxic to mites as many organochlorines, organophosphates are
particularly toxic to predatory mites.  Effects on other soil inverte-
brates were not well defined.  Parathion has long been considered high-
ly dangerous to bees (Eckert 1948) , but was acutely less toxic to hon-
eybees in the laboratory than dieldrin, azinphosmethyl, carbaryl, phor-
ate, or DDT (Johansen 1961).  Dusts were twice as toxic to bees as
sprays (Johansen et_ aL^. 1957).
Fish and amphibians—The toxicity of parathion to fish varies from a
96 hour TL  (median tolerance limit) of 0.055 ppm in guppies (Lebistes
reticulatus) to 2.7 ppm in goldfish (Carassium awcatus)3 with bluegills
(Lepomts maeroahirus) and fatheads (Pimephales promelas") intermediate
(Pickering _e_t al. 1962) .  Leudemann and Neumann (1961) found three mg/
liter (3 ppm) of parathion to be lethal to all rainbow trout (Salmo
iyideus') and pike fry (Esox luci-us') which were exposed while the no-
effect levels were 0.8 rag/liter (0.8 ppm) for trout and 1.0 mg/liter
(one ppm) for pike.  Spermatogenesis in guppies was decreased by ex-
posure to 0.1 to one ppm or parathion for more than six days; ten ppm
were lethal within hours (Billard et al. 1970).
Eisler (1970b) found that methyl parathion was less toxic to several
species of fish than were the organochlorines, Phosdrin, malathion, or
DDVP.  The 96 hour toxicity level of parathion was 5,200 to 75,800 ppb
in piscine species including the American eel (Angiulla PO strata"), blue-
                                   440
-------
heads (Thalasoma bifasaiatum'), striped killif ish  (Fundulus majalis"),
and striped mullet (Mugil cephalus').  Mulla and co-workers (1963)
found methyl parathion, at levels used in controlling mosquito larvae,
to be nontoxic to mosquitofish.  Parathion applied to ponds at 0.1  Ib/A
(0.11 kg/ha) killed 22 percent of the mosquitofish (Gambusia affinis)
added 30 hours after treatment (Mulla and Isaak 1961).  The toxicity
was greater over a period of  240 than over 96 hours in the estuarine
mummichog, Fundulus heteroclitus (Eisler 1970a).  Toxicity was in-
creased by increasing water temperature from 10   to 30 C, increasing
salinity, or decreasing the pH.  While the latter alterations in tox-
icity might be due to nonspecific stress effects, the increased toxi-
city after 45 minutes was undoubtedly due to paraoxon formation; great-
er toxicity of longer time periods  suggests cumulative action either
due to accumulation of toxicants, as with organochlorines, or progres-
sive toxicity, as in the neurotoxicity evoked by  some organophosphate
compounds.
Lee and Buzzell (1969) induced respiratory changes in goldfish with
0.56 mg/liter (0.56 ppm) of methyl  parathion although it took 3.20
mg/liter (3.2 ppm) for 65 days to kill the fish.  Burke and Ferguson
(1969) found that parathion was less toxic in flowing than static
solutions, presumably because of the accumulation of paraoxon under the
latter conditions.  DDT, toxaphene  and endrin, which do not require
activation, were more toxic in flowing solutions.  Mount and Boyle
(1969) hypothesized that more resistant species of fish might well ac-
cumulate parathion to some extent,  although the catfish they studied
(letalurus nebulosus") did not.
Parathion caused nerve cell injury  in both carp (Cyprinus aarpio L.)
and river crabs (Cambarus affinis Say) in a study by Kayser ert_ al.
(1962).   No data on piscine carcinogenesis, mutagenesis, or teratogen-
esis were found.  Resistance  to chlorinated hydrocarbon insecticides
did not confer parathion resistance on sunfish or shiners (Minchew and
Ferguson 1969).
                                  441
-------
Amphibians were found to be relatively resistant to organophosphates
(Mulla 1962).  In the toad, Bufo viridis, a lethal injection into the
dorsal lymph sac required 967 mg/kg of parathion or 188 trig/kg of para-
oxon (Edery and Schatzberg-Porath 1960).
Birds—The acute oral LD Q of methyl parathion is 6.12 to 16.3 mg/kg in
mallards and 5.7 to 11.9 mg/kg in pheasants (Tucker and Crabtree 1970).
Parathion has an acute oral LD   of 0.125 to 0.250 mg/kg in fulvous
tree ducks, 1.37 to 2.96 mg/kg in mallards, and 12.4 mg/kg in pheasants
(Tucker and Crabtree 1970).  Keith and Mulla (1966) found no definite
toxicity when mallards were fed five ppm parathion daily for five to
nine weeks, but 25 ppm were essentially lethal.  Heath and co-workers
(1972) calculated the LC   for five days of treated feed followed by
three days of clean feed to be 90 ppm of methyl parathion in bobwhites,
682 ppm for mallards, 46 ppm for Japanese quail, and 116 ppm for phea-
sants.  For parathion, the corresponding LC   was 44 ppm in Japanese
quail, 364 ppm in pheasants, with bobwhites and mallards intermediate.
Methyl mercury (Morsdren) was found to potentiate the action of para-
thion in coturnix quail (Dieter and Ludke 1975) .
Parathion was teratogenic in chickens if injected into the eggs (Up-
shall et_ al. 1968, Roger et al. 1969, Yamada 1972, Reis et_ _aJL_. 1971,
Dunachie and Fletcher 1969, Meiniel 1974) and in Japanese quail when
eggs were dipped into a ten percent solution (Meiniel et al. 1970,
Meiniel 1973).  Sterilization and feminization of treated offspring
were also observed (Lutz-Ostertag et al. 1970).
Mammals—Methyl paraoxon and paraoxon inhibit acetylcholinesterase in
mammals, and poisoning is due to the resulting potentiation of neural
synaptic transmission by acetylcholine.  Since the active agent in
cholinesterase inhibition is not the phosphorothionate itself, species
differences in sensitivity to parathion and methyl parathion may be
due to differing rates of conversion to the analogs (paraoxon and methyl
paraoxon), differing sensitivities of the cholinesterases to inhibi-
                                  442
-------
tion, or differing rates of metabolism of the oxygen analog (Murphy et
al. 1968).  A succinct review of the mechanisms of action and toxicity
of the organophosphates is presented by Fest and Schmidt (1973).
Both parathion and methyl parathion are readily absorbed through the
lungs or skin as well as by ingestion.  The minimum toxic level for a
human adult is estimated at 7.5 mg per day for parathion and somewhat
over 19 mg per day for methyl parathion (Rider et al. 1969).  Faerman
et al. (1969) found hematological abnormalities in workers producing
organophosphates:  iron-deficiency anemia, lower hemoglobin content,
and erythrocyte degeneration were observed.  The acute toxicity of
parathion in man is sufficiently great to warrant the conclusion that,
regardless of the expected degree of occupational exposure, almost any
person who works with parathion is in danger of being poisoned if he
is careless (Arterberry et al. 1961).
The acute oral LD   of parathion is 13 mg/kg in male and 3.6 mg/kg in
female rats; that of methyl parathion, 14 mg/kg in male and 24 mg/kg
in female rats (Martin 1968, Gaines 1969).  The acute oral LD   of pa-
rathion was 11 mg/kg in mice (Klimmer and Plaff 1955), 22-24 mg/kg in
mule deer and 28 to 56 mg/kg in domestic goats (Tucker and Crabtree
1970).  The acute dermal LD   of parathion in rats is 21 mg/kg in males
and 6.8 mg/kg in females (Martin 1968).
In tissue culture of normal cells (human skin fibroblasts) and malig-
nant cells (HeLa), it was observed that the direct cellular toxicity
of parathion was greater than that of paraoxon.  The direct cellular
toxicity of p-nitrophenol, the major terminal residue of parathion,
was as great as that of parathion itself (Litterst and Lichtenstein
1971).
Aldrin, chlordane, and DDT were found to protect somewhat against or-
ganophosphate poisoning (Triolo and Coon 1966, Williams et_ a^. 1967,
Chapman and Leibman 1971).  Triolo, Mata and Coon (1970) hypothesized
that rat serum aliesterases bind paraoxon, and thus the well established
                                  443
-------
enhancement of serum esterases by organochlorine insecticides mediated
paraoxon detoxification.  Parathion inhibits the metabolism of benzo-
(a)pyrene in rats (Weber et al. 1974) .
Parathion is embryotoxic in all species studied.  When female rats
were given methyl parathion three days  before parturition, methyl para-
oxon was found in all fetal tissues within twenty minutes (Ackermann
1974, Ackermann and Engst 1970).  Rat fetuses treated to day 17 were,
however, found to have normal levels of acetylcholinesterases, sugges-
ting that younger fetuses cannot convert parathion to paraoxon (Talens
and Wooley 1973).  Tanimura et al. (1967) reported normal litters from
rats treated on day 12 of pregnancy.  Leibovich (1973) reported de-
creased numbers of neonates and decreased survival among rats born to
dams who were fed parathion (0.1 to ten mg/kg) throughout pregnancy.
Embryotoxicity, but not teratogenesis,  was reported in offspring of
female rats fed 1.4 mg/kg/day of parathion for one week following mat-
ing (Noda et_ al. 1972).  Implantations  decreased and resorptions in-
creased.  Kimbrough and Gaines (1968) found parathion to be teratogenic
as well as embryotoxic in rats only if  maternal toxicity occurred.  In
mice, methyl parathion induced cleft palate (Tanimura e_t_ aJK 1967).
Rats were reportedly more sensitive to  parathion treatment in early
pregnancy than were hamsters (Lauro et  al. 1969) .  Data on other spec-
ies of laboratory mammals were not available.
The sum of these data is that parathion is acutely toxic and exerts
considerable stress on the maternal organism; direct effects on the
embryo have not been ruled out, but have not been seen in the rat.
There are no data available suggesting that parathion and methyl para-
thion are either carcinogenic or mutagenic.  Data to the contrary were
also not available.
Conclusions-
The major hazard of parathion and methyl parathion in ordinary usage
is clearly in their acute toxicity to mammals, birds, beneficial ar-
                                  444
-------
thropods and fish.  When applied at reasonable levels in the natural
environment, parathion and methyl parathion are degraded within weeks.
In the interim, transport can occur from soil into water and from
water into sediment.  Volatilization inevitably occurs from soil fur-
faces and from foliage, and quantifiable residues are taken up by food
plants.  Nevertheless, the relatively rapid detoxification of these
compounds by microbial degradation and by hydrolysis assures dissipa-
tion.
Under conditions of bulk disposal, however, degradation is significantly
retarded (Naishtein et al. 1973) even when the massive treatments are
soil-mixed, as would occur in spills.  If 31 pounds per acre are ap-
plied, residues are found for sixteen years (Stewart et_ a^. 1971),
while potentially lethal residues are found in the top inch of soil for
five years after the equivalent of 190,000 Ibs/A were applied.  These
data argue strongly against bulk disposal of parathion in the soil.
Moreover, there are too few data available on the persistence, soil
toxicity, and motility of p-nitrophenol and other metabolites of para-
thion to permit evaluation of their effects on the environment.
Nonbiological degradation of parathion production wastes is feasible,
but requires extensive cleanup procedures (Stutz 1966).  More plausible
would be controlled microbial degradation, preferably in a two-phase
process which permits anaerobic detoxification followed by aerobic
ring-cleavage as described by Sethunathan (1973a, 1973b) and by Sethu-
nathan and Yoshida (1973a, 1973b).  No data are available on the feas-
ibility of such a process on a large scale.
                                  445
-------
Malathion
Malathion is the common name for  5-1,2-bis-(ethoxycarbonyl)ethyl  0,0-^,
dimethyl phosphorodithioate, introduced by the American Cyanimid Com-
pany in 1950 as Malaphos.  Its common name in West Germany and South
Africa is mercaptothion; 5.n the USSR, carbofos.  Malathion is prepared
by the addition of 030-dimethyl phosphorodithioic acid to diethyl mal-
eate in the presence of hydroquinone (Martin 1968).  It is yellow to
dark brown liquid with a melting point of 2.85 C, a boiling point of
156  to 157 C at 0.7 mm mercury, and a vapor pressure of 4 x 10   mm
mercury at 30 C.  Its solubility in water is 145 ppm at room tempera-
ture and light petroleum oils are soluble to about 35 percent malathion.
It is formulated as emulsifiable concentrates, dusts, and atomizing
concentrates for use as a nonsystemic insecticide and acaricide.
Degradation-
Walker and Stojanovic (1973) analyzed the relative contributions of
chemical and biological reactions to the degradation of malathion in
soil.  They concluded that microbial degradation predominated, but
that increasing pH or soil organic matter increased the importance of
hydrolysis.  The relative contributions of chemical and biological
reactions in three soils are shown in Table 66, and data on biological
degradation are summarized in Table 67.
Biological—Neither Trichoderma wivi-de nor Pseudomonas converted mala-
thion to malaoxon, although both degraded malathion (Matsumura and
Boush 1966).  Soil fungi (Pennicilium notation, Aspergillus niger) were
able to degrade three mg malathion per 100 ml nutrient solution  (30
ppm), but Ehizocton-ia solani was inactivated at this level, although
active at two mg malathion per 100 ml nutrient solution (20 ppm) (Mos-
tafa et al. 1972b) .  Rhizobiwn tvifo1i.-i degraded 95.5 percent of mala-
                                  446
-------
     Table 66.  DEGRADATION OF MALATHION IN THREE SOILS
     OVER A 10 DAY PERIOD (WALKER AND STOJANOVIC 1973).
                      Total%%
	Degradation (%)    Chemical	Biological
Loam                   100              9            91
Sand                    99              5            95
Clay                   100             23            77
Loam-water              85             40            60
Sand-water              29              3            97
Clay-water              75             47            53
                            447
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thion within one week with only 0.5 percent being converted to malaoxon
(Mostafa et_ al^. 1972a) .  Getzin and Rosefield  (1968) reported a stable,
cell-free soil enzyme which converted malathion to its monoacid; the
enzyme was resistant to heat, dessication, and microbial destruction.
Sethunathan and Yoshida (1973a) identified a Flaoobaateviwn which de-
graded parathion and diazinon but not malathion.  In alkaline soils,
adsorption reportedly preceded degradation (Konrad et ajl. 1969).
Malathion was readily degraded by sewage lagoon microorganisms  (Halvor-
son £t_ al_. 1971).  In activated-sludge sewage  systems, the volume of
organic matter was better correlated with the degree of degradation
than was the volume of water.  A ratio of  malathion:microorganism  ::
1:5  or less inhibited microbial degradation (Randall et^ SL^. 1967).  In
surface water the rate of malathion degradation by natural and sewage
microorganisms increased for five days, presumably reflecting changes
in microbial populations (Jirik &t_ al. 1971) .
Malathion sufficed as the sole source of carbon for a heterogeneous
collection of bacteria from aquatic culture, but degradation proceeded
only to the malathion-beta monoacid, which remained stable for at least
4.5 months (Paris et^ aJ^. 1975).  An aquatic fungus, Aspergillus oryzae,
also converted malathion to its monoacid, producing ethanol as a by-
product, which served as a carbon source for the fungi.  Fungal trans-
formation was, however, much slower than the bacterial transformation
(Lewis et al. 1975).  In a microbial salt-marsh ecosystem, malathion
was rapidly decomposed by indigenous bacteria, with a relatively insig-
nificant contribution by those bacteria which use malathion as their
sole source of carbon.  The major agents of degradation were carboxy-
esterases and some phosphatases (Bourquin 1975).
Paraoxon residues on plants inhibited malathion dissipation from plums,
tomatoes, and string beans after harvest; neither parathion nor mala-
thion itself was inhibitory (Koivistoinen et al. 1964).  Aldrin pre-
                                   449
-------
treatment, in contrast, increased malaoxon degradation (Cohen and Mur-
phy 1974).  Wheat seed-coat enzymes converted malathion to its thio-
late and phosphate (Rowlands 1966), and in rice grains malathion is
converted to thiophosphoric acid (Tomizawa et al. 1962).
Malaoxon is produced from malathion by mouse liver (O'Brien 1957),
where its inactivation depends on an esterase highly sensitive to oth-
er organophosphates.  Therefore, the toxicity of malathion can be
sharply increased by the presence of other organophosphates (Cook et
ail. 1957, 1958).  A lactating cow which was fed 63 ppm malathion for
three days excreted 77 percent within one week; the remainder had not
been excreted after three weeks (O'Brien et_ al_. 1961).
In an aquatic-terrestrial ecosystem, malathion was exceptionally de-
gradable:  no traces of the parent compound were found in any of the
organisms.  The fish, snails, and mosquito contained several uncharac-
terized metabolites, which were also found in water (Metcalf and San-
born 1975).
Photolytic—Mosher and Kadoum (1972) analyzed the dissipation of mala-
thion from surfaces under the influence of light.  Themmost rapid de-
gradation was observed with infra-red light and was due to the heat
generated (119 C).  Far ultraviolet was a more effective light source
for degrading malathion, than near ultraviolet light.  Decomposition
products included malaoxon, malathion monoacid, malathion diacid, 0,0-
dimethyl phosphorothioic acid, dimethyl phosphate, phosphoric acid,
and unidentified products.  Malathion disappeared most rapidly from
glass beads, and least rapidly from wheat grains.  Sorghum grains were
intermediate (Mosher and Kadoum 1972).
Anthraquinone accelerated the photodecomposition of malathion on silica
gel chromatographic plates (Ivie and Casida 1971).  After 16 hours of
exposure to ultraviolet light at 37 C, 66 percent of the malathion had
disappeared from ladino clover (Archer 1971).  Wolfe and co-workers  (1975),
using wave lengths above 290 nm, estimated the photolytic half-
                                    450
-------
life of malathion to be 990 hours (41.25 days) in water at pH 6, but
only 16 hours in Suwannee river water which contained large amounts of
colored material.
Chemical—Malathion was more rapidly degraded in clay loam in which
heat-labile substances had been destroyed than in the original soil
(Getzin and Rosefield 1968).  In water at pH 10, malathion decomposed
to the dimethyl phosphate and succinic or thiosuccinic esters (Shev-
chenko et al. 1974).  Degradation is extremely rapid at high pH (Paris
and Lewis 1973) but proceeds quite slowly at low pH, and Wolfe et al.
(1975) reported that malathion persisted for up to two weeks in oxygen-
saturated acidic water.  Spiller (1961) could not detect degradation
after 12 days at pH 5.0 to 7.0, and similar results were obtained for
pH 2.0, 4.0, and 6.0 (Konrad et al. 1969).  In neutral solution, mala-
thion was 70 percent hydrolyzed in one week (Cowert et al. 1971).
Of malathion formulated in Zeeklite (a quartz cristobalite) 8.4 to 9.2
percent had decomposed after 30 days at 40 C, while 36.9 percent of
the malathion formulated on clay L had decomposed in the same period
(Takehara et al. 1967b).  The decomposition of dusts was not affected
by moisture but was catalyzed by copper, lead, mercury or tin (in de-
creasing order of efficacy) while the decomposition of emulsions in-
creased with increasing moisture (Yamauchi et al. 1959).  When mala-
thion was applied to a calcareous (alkaline) West Point loam at the
equivalent of 11,227 kg/ha (five tons per acre), carbon dioxide evo-
lution decreased if analytical grade malathion was used, but increased
when formulated malathion was used, presumably due to degradation of
the carrier (Stojanovic et^ al. 1972a).
Malathion was completely degraded by treatment with liquid ammonia and
metallic sodium or lithium (Kennedy et_ auL. 1972a).  Treatment with 8N
sodium hydroxide decomposed malathion to inorganic phosphate, while
I5N ammonium hydroxide partially decomposed it (Kennedy et_ al_. 1972b).
Ozone treatment of malathion-contaminated water reportedly decreased
                                 451
-------
the toxicity of the water (Gabovich and Kurennoi 1966).
Physical—Cobalt-60 
-------
et_ al_. 1969), but when malathion was  used  to  disinfect  stables,  0.08
to 0.28 ppm were detected  in  the milk for  up  to  three months  (Milhaud
et^a^. 1971).
Carp exposed to 2.5 mg/liter  of malathion  (2.5 ppm)  for four  days  ac-
cumulated 7.91 + 2.27 mg/kg in their  livers  (Bender  1969).  In a salt
marsh in northwestern Florida, 0.42 kg/ha  were applied  in  three  fog-
gings at two week intervals and blue  crabs (Callineetus sopi-dus} ,  grass
shrimp (Palaemonetis vulgaris, Palaemonet-Ls pugio),  pink shrimp  (Pen-
aeus duoramon) and sheepshead minnows (Cypr-inodon varietgatus) confined
in the treated area contained no measurable residues of malathion, nor
did snails (Littorina irrorarata'), but plants (Juncus sp.)  contained
0.05 to 0.10 ppm malathion for up to  14 days.  Water retained traces
of malathion for one day  (Tagatz et al. 1974).
Volatilization-
Ethanol solutions of malathion were evaporated to dryness  on  watch
glasses and kept at 35 C for  90 days.  Not more  than 7.5 percent of the
malathion volatilized in the  first fifteen days; 41  to  49  percent had
volatilized after 90 days; and the lower levels  of volatility were ob-
served with malathion of greater purity (Alessandrini and  Amormino
1954).
Persistence-
The persistence of malathion  in soil, in water,  and  on  organisms is
summarized in Table 68.  Malathion residues were found  in  43  percent
of the soils sampled in five  west Alabama  counties (Albright  et  al.
1974).  Malathion was more persistent in muck than in soil  with  low
organic matter content and soil residues of malathion after eight days
were said to be three percent (Lichtenstein 1965).   Krishnan  and co-
workers (1958) claimed five week residual  effectiveness  for water-dis-
persible malathion powders.   Chopra and Girdhar  (1971)  found  persis-
tence to increase with increasing pH, decreasing relative humidity,
                                  453
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increasing concentration, and decreasing exposure to ultraviolet light.
On plants, ultralow volume sprays were approximately twice as persis-
tent as emulsified concentrations (Saini et al. 1970).
In water, malathion is hydrolyzed almost instantly at pH 12, but not
at all at pH 5 to pH 7 (Spiller 1961) .  Paris and Lewis (1973) sugges-
ted that malathion may be relatively persistent in aquatic systems be-
cause it is not rapidly destroyed at neutral pH but in samples of riv-
er water ranging from pH 7.3 to 8.0, malathion residues after seven
days were 25 percent of the original level and after four weeks no
malathion was detectable (Eichelberger and Lichtenberg 1971).  Menzie
(1972) characterized the persistence of malathion in water as "variable",
but noted that it persisted less than one day in fish.  In cattle, 2.7
           32
percent of   P-malathion remained in the hide after two weeks (March
et al. 1956).
Very little has been published on the fate of non-insecticidal metabo-
lites of malathion.  Lenon and co-workers (1972) reported the presence
of an unidentified metabolite of malathion in all of 49 cisterns tested
on the Virgin Island while malathion itself was present in only two of
the cisterns, at levels of 0.01 ppb and 0.14 ppb.  Paris et_ a\^. (1975)
reported that both ieta-malathion monoacid and malathion diacid were
stable for 4.5 months in aquatic cultures.
Effects on Non-Target Species-
Microorganisms—Malathion was not mutagenic in Eschepi-ehia eoli under
conditions in which a number of organophosphates were mutagenic (Mohn
1973).  Yurovskaya and Zhulinskaya (1974) claimed that any effects of
malathion on soil microorganisms were only temperary.
The effects of malathion on aquatic microorganisms are summarized in
Table 69.  Algae were considered less sensitive to malathion than either
protozoa or rotifers (Ranke-Rybicka and Stanislawska 1972); DaSilva and
co-workers (1975) reported that malathion at a level of 100 ppm initially
                                   455
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inhibited algal growth and subsequently stimulated it.  One species
among nine algae tested, (Cylindpospermum musoiaola) was already ex-
ceeding control growth after one hour; one species (Nostoc derived
from Collematenax) never reached the control levels of growth.  The
other seven species (See Table 69) were below control levels after one
hour, and well above after 28 days.  In sewage disposal lagoons, levels
of malathion as low as one ppm caused 0.83 percent mortality (Steelman
et al. 1967).
The effects of malathion on soil processes and soil microorganisms are
summarized in Table 70.  At 10 pg/ml (10 ppm) malathion completely in-
hibited Nitrosomonas europaea, but 1000 yg/ml (1000 ppm) were required
to inhibit Nitrobaater agilis (Garretson and San Clemente 1968).  In an
upland Novalickes clay loam, malathion decreased the total nitrogen
concentration of the soil, and first decreased, but then increased,
soil levels of phosphorus and calcium (Vicario 1972).  Gram-positive
bacteria were more sensitive to malathion than gram-negative bacteria
(Nestor 1972) and malathion was toxic both to entomogenous fungi and
to pathogenic fungi (Hulea and Piticas 1973).  Aflatoxin synthesis in
Aspergillus was inhibited by malathion (Hsieh 1973).
At five tons per acre  (11,227 kg/ha), formulated malathion strongly in-
hibited bacteria and streptomyces, and slightly inhibited fungal growth.
Malathion itself inhibited bacterial growth  slightly, and stimulated
streptomyces (Stojanovic et^ a^. 1972a).
Invertebrates—Malathion applied to white clover (Trifolium repens") at
1.25 Ibs/A (1.39 kg/ha) of wettable powder or emulsifiable concentrate
was not residually toxic to honeybees (Clinch 1969), but 0.50 to 0.75
Ibs/A (0.61 to 0.84 kg/ha) was toxic to all  bees in the field (Ander-
son and Atkins 1958).  A 48 hour exposure to malathion reportedly in-
creased tolerance of copepods in the contaminated areas to malathion
(Naqvi and Ferguson 1968, 1969).  In treated and control areas  of a
pine hardwood forest, microarthropod populations did not differ one
                                   457
-------














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year after treatment of podzol soil with  2  Ibs/A  (2.24 kg/ha)  of raala-
thion (Hartenstein 1960), but MacPhee and Sanford  (1956)  described  the
effects of raalathion on beneficial arthropods in Nova Scotia apple  or-
chards as drastic.
The knock-out level of malathion for Dctphnia magna was ten ppm for  19
minutes (Klimmer and Plaff 1955), while the median tolerance limits
for freshwater shrimp (.Gcamarus locustTis) was 0.00162 mg/1  (0.00162
ppm) (Gaufin et^ al. 1965).
Fish and amphibians—Malathion is less toxic to fish than endrin or
endosulfan (Toor et al. 1973).  All rainbow trout  (Salmo  ir-ideus) died
when exposed to one mg/liter  (one ppm); the 96 hour LC    was 0.17 ppm
(Pimentel 1971).  In ponds, 0.5 Ib/A (0.56 kg/ha) of malathion killed
48 percent of the mosquitofish (Gambus-uz  aff^nis) which were placed in
the water after 24 hours, and 70 percent  of those placed  in the water
48 hours after malathion treatment (Mulla and Isaak 1961).  Emulsifiable
concentrates were more toxic than technical grade malathion to four
species of warm-water fish, but the difference was slight (Pickering
et_al. 1962).
Birds—The acute oral LDsn for young mallards was 1485 mg/kg,  and the
LC,.-. was over 5000 ppm when two week old  birds were fed treated feed
for five days followed by clean feed for  three days (Pimentel  1971).
Feeding of 0.1 ppm malathion decreased egg production in  hens  (Sauter
and Steele 1972).  Transient paralysis lasting for four to 14  days
was observed in chickens given 100 mg/kg  of malathion (Gaines  1969).
In tissue culture, the ID(-0 (the dose causing 50 percent  growth inhi-
bition) of malathion on embryonic chick muscle was between ten and
100 ppm (Wilson et al. 1973).  Malathion  caused hypoglycemia and in-
creased histogenesis of the islets of Langerhans in chicken embryos
(Arsenault and Gibson 1974).
Injection of malathion into the yolks of  hens' eggs caused malforma-
tions of legs and beaks (Walker 1971; Greenberg and LaHam 1969, 1970;
                                   459
-------
Mclaughlin et^ sd. 1963; Dunachie and Fletcher 1969; Roger et^ a^. 1969).
Levels as low as 15 yM were effective, and cholinesterase inhibition
was not the basis for teratogensis, which could be prevented by nico-
tinamide (Walker 1971).  Quinolinic acid, nicotinic acid, glycine, and
tryptophan also decreased the incidence of malformations but only tryp-
tophan prevented growth retardation (Greenberg and LaHam 1970).
Mammals—The inhibition of cholinesterase by malaoxon is minimal in
mammals because of the rapid hydrolysis of malaoxon (Cook et_ al. 1958,
Murphy et al. 1968, Dauterman and Main 1966).  The acute oral LD_. of
                                                                50
malathion in rats is 1,000 mg/kg in females and 1,375 mg/kg in males
(Gaines 1969):  Jones £t a^. (1968) cited 1,400 and 1,900 mg/kg.
Among the reported effects of sublethal doses of malathion are hyper-
glycemia in rats given a subclinical dose of two to 2.5 mg/kg subcut-
aneously (Ramu and Drexler 1973) and decreased nidation and increased
early resorption in rats given malathion four to eight days after in-
semination (Lauro £t_ aL. 1969).  In tissue culture, malathion at 200
to 400 pg/ml (200-400 ppm) inhibited mitoses (Huang 1973); growth of
Chang liver cells could be inhibited by 15 yg/ml (15 ppm) (Gabliks and
Friedman 1965).  Malathion also inhibited the in vitro replication of
vaccinia and poliomyelitis viruses (Gabliks 1967).  In rats treated
with 4,000 mg/kg (4,000 ppm) for two generations, the only adverse ef-
fect reported was an increase in ringtail disease in the second gener-
ation (Kalow and Marton 1961).
In humans, malathion is a moderately potent allergen, with allergies
occurring under field conditions (Milby and Epstein 1964).  Danilov
(1968) recommended a distance of 1,000 meters between areas of malathion
production and human or animal habitations, because of the hazards of
byproducts and waste products.
Conclusions-
The rapid degradation of malathion makes it eminently suitable for soil
disposal because of its short persistence and minimal effects on soil
processes.
                                   460
-------
Diazinon
Diazinon is the coiranon name for 0,0-diethyl £>-6-methyl-2-(l-methyl-
ethyl)-4-pyrimidinyl phosphorodithioate, introduced by the Geigy Chem-
ical Company in 1952 as Basudin.  It is a nonsystemic insecticide with
some acaricidal activity.  Diazinon is prepared by the condensation of
diethyl phosphorochloridothionate with 2-isopropyl-4-methyl pyrimidin-6-ol,
which was in turn prepared by the condensation of isobiityramidine and
ethyl acetoacetate (Martin 1968).  It is a colorless oil with a boiling
point of 83° to 84°C at 0.002 mm Hg and a vapor pressure of 1.4 x 10
mm Hg at 20 C.  Its solubility in water is 40 ppm at room temperature
and it is readily miscible with ethanol, acetone, and xylene.  It is
also soluble in petroleum oils.  Technical diazinon is a dark brown
liquid of approximately 95 percent purity.
Degradation-
Biological—Diazinon is degraded in soil by a combination of microbial
and chemical reactions.  The initial step is the hydrolysis of the het-
erocyclic P-0 bond, resulting in formation of diethylthiophosphoric
acid and 2-isopropyl-4-methyl-6-hydroxyprimidine (Getzin 1967, Lich-
tenstein ejt al. 1968, Bartsch 1973).  The latter product is resistant
to further degradation under anaerobic conditions, (Sethunathan 1972a,
Sethunathan and Yoshida 1969, 1973a).  Sethunathan and MacRae (1969)
considered chemical hydrolysis to precede microbial action, but Seth-
unathan (1972a) subsequently reported greater persistence of diazinon
in sterilized than in normal soil, and also noted increased hydrolysis
of diazinon after repeated applications (Sethunathan 1972a, 1972b).
Microbial degradation of diazinon is summarized in Table 71.
Tetraethylpyrophosphate was cited as one product of microbial diazinon
degradation (Paris and Lewis 1973).  A Flavobacteriwn species isolated
                                    461
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                                                   14
from paddy water was able to convert 30 percent of   C-labeled diazi-
non to carbon dioxide, with intermediate formation of 2-isopropyl-6£
methyl-4-hydroxyprimidine; diazinon itself was 95 percent depleted
within 72 hours  (Sethunathan and Yoshida~1973a).  Diazinon was more
rapidly degraded in sand than in loam, and more rapidly in moist  than
in dry soil; steam-treating the soil affected persistence more than
soil type, moisture levels, or concentration  (Bro-Rasmussen et al.
1968).  Decreased diazinon degradation due to destruction of heat-
labile soil substances was not observed by Getzin and Rosefield  (1968).
However, hydrolysis of diazinon to diethylthiophosphoric acid and 2-£.
isopropyl-4-methyl-6-hydroxypyrimidine occurred readily in the presence
of sodium azide  (Lichtenstein et al. 1968).
When diazinon was applied to the surface of paddy soil, emulsions were
more rapidly degraded than granules (Masuda and Fukada 1970).  In a
New York State muck soil, addition of marl (a finely powdered mixture
of calcium carbonate and clay) speeded diazinon degradation in unster-
ilized soil, but retarded it in autoclaved soil (Kageyama et^ a^.  1972).
Nasim and co-workers (1972) reported that the degradation of diazinon
in Dacca paddy field soil was carried out by unidentified, heat-labile
substances; degradation reportedly proceeded for 24 hours and then
stopped.
Among the specific organisms which have been found to degrade diazinon
are Arthrobaeter and Streptomyees acting together (Gunner and Zucker-
mann 1968); Streptomyces alone in the presence of glucose (Sethunathan
and MacRae 1969); TT-Ldhoderma vivide (Matsumura and Boush 1968) and
FlavobaoteTium (Sethunathan and Yoshida 1972a, 1973a).  The latter also
degraded parathion, but not malathion (Sethunathan and Yoshida 1973a).
Two of eight microbial colonies tested by Hirakoso (1969) were able  to
degrade diazinon.  Microorganisms from sewage lagoons degraded diazi-
non less readily than either malathion or parathion (Halvorson et al.
1971).  In mosquito-breeding polluted x^ater, diazinon remained unaltered
                                  463
-------
for days if the medium was alkaline (Hirakoso 1968).  Diazinon was re-
moved from culture by all planktonic algae tested, but no estimates of
degradation were made (Butler et^ al. 1975).
Pseudomonas melophthora} the intestinal symbiote of the apple maggot,
degraded diazinon to some extent, with 71 percent of the diazinon re-
maining unmetabolized, 26.7 percent converted to water-soluble sub-
stances, and 2.4 percent to solvent-soluble substances (Boush and Mat-
sumura 1967).
In plants, metabolism was primarily due to hydrolysis of the pyrimi-
dinylphosphorus ester bond with foliage the main site of hydrolysis.
Accumulation of 2-isopropyl-4-methylpyrimidin-6-ol, and possibly of
conjugated metabolites, occurred in the leaves (Kansouh and Hopkins
1968).
Rat liver microsomes were capable of degrading diazinon in vitro to
diethylphosphorothioic acid and diethyl phosphoric acid (Yang et^ al.
1969); in vivo, rats excreted 50 percent of the radioactivity from
14
  C-diazinon labeled at the pyrimidine and ethoxy moieties.  No pyri-
midine ring cleavage was detected (Muecke et^ al. 1970).  Rats hydrolyzed
the alkyl-P bond of diazinon to form diethylphosphoric acid at high
levels of diazinon treatment.  At lower levels, hydrolysis of the
aryl-P bond was the primary degradative pathway (Plapp and Casida 1958).
Sheep treated with diazinon excreted hydroxy-diazinon and its isomer,
diethyl-6-hydroxymethyl-2-isopropyl-4-pyrimidinyl phosphorodithionate,
in their urine (Machin et al. 1972) .  Dogs excreted 50 percent of the
                       14
total radioactivity of   C-labeled diazinon in their urine within 24
hours; 16 percent as diethylphosphoric acid and 45 percent as diethyl-
thiophosphoric acid (Iverson e_t^ al. 1975).
Chemical and physical—Hydrolysis of diazinon in soil was considered
to be adsorption-catalyzed rather than acid-catalyzed, was more rapid
in soil than in water, and was extremely rapid at pH 2, but slow at
pH 6.  Degradation was most rapid in Poygan sand (11 percent per day)
                                  464
-------
and least rapid in Ella sediments  (six percent per day); Kewaunee dolo-
mitic till was intermediate.  Hydrolysis was considered more signifi-
cant than bacterial action in the degradation of the parent compound
(Konrad et^ al_. 1967).  In water between pH 3.1 and pH 10.4, diazinon
was hydrolyzed to 2-isopropyl-4-methyl-6-hydroxypyrimidine at differ-
ent rates although first-order kinetics applied to all pH tested.
Diazinon persisted for less than 145 hours at pH 10.4, over 3200 hours
at pH 9.0, and over 4435 hours at pH 7.4 (Gomaa et_ al^. 1969).   It was
reported that formulated diazinon degraded during storage to form tet-
raethylmonothiopyrophosphate (Mello et al. 1972).
Photolytic—Ultraviolet irradiation of diazinon results in formation
of hydroxydiazinon (Paris and Lewis 1973).  Photolytic degradation of
diazinon was catalyzed by anthroquinone and to a lesser extent  by pen-
tachlorophenol (Ivie and Casida 1971).
Transport-
Within soil—The biological activity of diazinon in soil depends both
on soil type and on the soil moisture.  Diazinon is more toxic  in min-
eral soil than in muck (Harris and Mazurek 1966a).  It is more  toxic
in moist than in dry clay or sand  (Harris 1966b) but the effect is more
pronounced in sand; diazinon is somewhat more toxic in dry muck than
wet muck (Harris 1964a, 1964b).
Diazinon was more mobile in brown forest soil than in either degraded
chernozem or marsh soil, and was more mobile in soil than either phor-
ate or lindane (Ostojic et_ al. 1972).  The diffusion coefficient of
diazinon in a silt loam was calculated to be 0.63 mm  per day at 27 C,
and increased with increasing temperature, decreasing soil bulk density;
and, to a lesser extent, with increasing moisture (Ritter et^ al^. 1973).
In 17.8 cm soil columns, diazinon was more mobile than triazine herbi-
cides, chlorinated hydrocarbon insecticides, phorate, or disulfoton
(Harris 1969a).
                                  465
-------
Between soil and water—Diazinon was completely eliminated from a model
cranberry bog seven days after application (corresponding to six days
after the bog was flooded); microflora were considered the main agents
of degradation, but both fish and mussels accumulated diazinon.  After
144 hours (six days), diazinon had been completely removed from the
water (Miller et_ al_. 1966).  On a small agricultural watershed, the
loss of diazinon in surface runoff or sediment was considered insigni-
ficant (Ritter et^ a^. 1974).
Volatilization—Volatilization accounted for the loss of 86 percent of
the diazinon on watch glasses over a 90 day period at 35 C.  Loss of
77.5 percent occurred within the first 15 days (Alessandrini and Amor-
mino 1954).
Into organisms—Diazinon was taken up by the roots of bean plants and
translocated within plants.  If the roots were subsequently rinsed and
placed in nutrient solution, diazinon migrated from the roots into the
nutrient solution (Kansouh and Hopkins 1968).  Cabbages watered with
two ppm of diazinon contained 0.01 ppm after 30 to 40 days, and tobac-
co contained 0.02 ppm after 56 days (Miles et^ al_. 1967).
In spinach, diazinon accumulated at more than one ppm in the leaves,
and at up to 60 ppm in the roots, when the soil was treated with 10 ppm;
residues in strawberries remained below 0.1 ppm, and no diazinon resi-
dues were detected in onions even when soil levels were 100 ppm (Kono
1974).  In rice paddies, diazinon applied to the water was absorbed by
the leaf sheath of the plants whereas soil-applied diazinon was absor-
bed through the roots; in the latter case, none of the radioactivity
was released into the water (Hirano and Yashima 1969).  The maximum
residues of diazinon in rice plants occurred five days after treatment
(Sethunathan et_ al. 1971) .
           32
Emulsified   P-diazinon was more rapidly taken up into rice leaves from
paddy soil than were granules.  Residues of the former reached their
                                  466
-------
highest levels in leaves within one day of treatment, while leaf resi-
dues after granule treatment rose continuously for 16 days after treat-
ment (Masuda and Fukada 1970).  The major metabolites in rice leaves
were (C2H50>2P(0))H, 50.4 percent;  (C2H50)2P(S)OH, 31.1 percent; H3P04
and P(S)OH«, 7.2 percent.  In rice ears, the major metabolite (85.9
percent) was (C_H 0)P(0)OH (Masuda and Fukada 1970).
Persistence-
Sterilizing soil by steam treatment reportedly increased the persis-
tence of diazinon more than altering the type of soil, its moisture,
or the level of diazinon applied (Bro-Rasmussen et al. 1968).  Sethu-
nathan (1972a) and Sethunathan and MacRae (1969) reported that steri-
lization increased the persistence of diazinon in all soils except
acid clays (pH 4.7).
Decreasing the temperature of the soil from 35  to 15 C increased the
persistence of diazinon by a factor of eight (Getzin 1968); in another
study,  reducing the soil temperature from 24  to 13 C lengthened the
period of bioactivity of diazinon against a test insect (Folsonria oan-
dida) from less than six weeks to 16 weeks (Thompson 1973).  Decreas-
ing the soil moisture from 30 percent to 2 percent of field capacity
increased the soil "half-life" of diazinon from six weeks to 16 weeks
(Getzin 1968).  The effects of soil type, temperature, moisture, and
sterilization all interact in determining the persistence of diazinon
(Ero-Rasmussen et^ al. 1968).  At 90°F and 55-5 percent relative hu-
midity, bioactivity of diazinon reportedly persisted for 29 days (Kal-
kat e^ al. 1961).
Kageyama et al. (1972) reported that the addition of marl (a finely
powdered mixture of calcium carbonate and clay) halved the persistence
of diazinon in ordinary muck soil, but enhanced its persistence in
sterilized muck soil.  After seven months in sandy loam soil, one per-
cent of two kg/ha diazinon remained, but ten percent remained in peaty
loam (Suett 1971).  Diazinon residues of 13 percent remained in hen-
                                 467
-------
house litter after four weeks, (Galley 1972) and 4.6 percent remained
in neutral aqueous medium after five weeks  (Cowert et al. 1971).
Under ordinary agricultural conditions, the biological persistence of
diazinon ranges between two and four weeks  (Krishnan et_ al_. 1968, Get-
zin and Rosefield 1966, Bro-Rasmussen et^ al_. 1968, Harris 1969b, Harris
and Hitchon 1970).  Read (1969) reported that the effectiveness of
diazinon in mineral soil decreased steadily for one month and then re-
mained nearly unchanged for during the second and third month.  In a
newly developed irrigation district, foliar sprays of diazinon left
initial residues of up to 3.34 ppm in the soil, which decreased to
0.02-0.05 ppm within 1.5 to 2.5 months (Knutson et^ al. 1971).  When
two to four times the normal agricultural levels of diazinon were ap-
plied to a carrot field, less than 0.3 ppm remained in the soil 42 days
later (Stobwasser 1963), and when 400 g/A (about 0.45 ppm) were sprayed
on field-grown lettuce, somewhat less than 0.1 ppm (22 percent) were
detectable after ten days (Coffin and McKinley 1964).
In rice, diazinon was detected at 0.004 ppm 53 days after treatment
with 2.5 kg/ha (Masuda and Kanazawa 1972).  When soil was treated with
6 ppm, diazinon residues in the plant Impatiens batsami were detectable
for 63 days (Augustinsson and Johnsson 1957).
Data on the persistence of diazinon are summarized in Table 72 for those
studies in which the residue remaining after a specific length of time
could be calculated.  In summary, diazinon is most persistent if in-
corporated at high levels into a cold, dry, alkaline soil which has
never before been exposed to diazinon or parathion.  It is least per-
sistent if sprayed at low levels onto a warm, moist, acid soil which
has been repeatedly treated with diazinon.  Under the former conditions,
diazinon might be expected to persist well over three months, while
under the latter conditions it would be dissipated, if not degraded,
within two to three weeks.
                                  468
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Effects on Non-Target Species-
Microorganisms—Diazinon was not mutagenic in Esaherichia ooli- under
conditions in which several organophosphorus compounds were mutagenic
(Mohn 1973).  Diazinon, but not its metabolites diazinon-oxon, diethyl-
phosphorothioate, and 2-isopropyl-4-methyl-6-hydroxyprimidine, markedly
inhibited the growth of heterotrophic aerobic bacteria (Robson and
Gunner 1970).  At 40 to 120 kg/ha, diazinon formulated as Basudin in-
hibited nodule formation in red clover  (Trifolium pvatense) grown on
sandy soil.  Nodule formation was also  inhibited in alfalfa (Medioago
sativa) grown on chernozem.  If applied at 80 to 120 kg/ha, diazinon
decreased the nitrogen content of the clover (Salem et al. 1971).
At 100 yg/g  (100 ppm), diazinon stimulated fungal growth for one week.
Ammonification increased and nitrification decreased, but overall soil
respiration was not affected (Tu 1970).  At high levels, diazinon in-
hibited mycelial growth in the fungus Aspergillus (Eder 1963), but
neither the growth nor the carbon-14 assimilation of the freshwater
alga Scenedesmus quadriaaudatus was affected by diazinon in the culture
medium (Stadnyk -ifoliwn repens) at
1/8 pound per acre (0.14 kg/ha) of a 40 percent wettable powder caused
28 percent mortality to bees present on the clover: residual toxicity
after three hours was 78 to 92 percent mortality if 1/4 pound per acre
(0.28 kg/ha) was sprayed (Clinch 1969).  In soil, diazinon decreased
the numbers of parasitic mites and of paurapods; the numbers of spring-
tails increased (Edwards et al. 1969).  Increases in the numbers of
springtails were secondary to decreases in the numbers of predatory
                                 471
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mites  (Edwards and Thompson 1973).  In an old-field ecosystem,  species
diversity and density increased in the year following  treatment with
14 Ibs/A (15.7 kg/ha) of diazinon (Malone et_ al. 1967).
Plants—Diazinon at 14 Ibs/A  (15.7 kg/ha) increased root growth and de-
creased shoot growth in an old-field ecosystem; the number and density
of plant species increased for up to one year after treatment  (Malone
et^al. 1967).
High levels of diazinon reportedly inhibited both shoot and root growth
in higher plants (Eder 1963), but Dennis and Edwards  (1963) did not
consider diazinon phytotoxic.
Fish and amphibians—Diazinon was not toxic to young rainbow trout
(Salmo i-vldeus} at 0.1 mg/liter (100 ppm), caused some deaths at 0.4
mg/liter (400 ppm), and killed all the trout at 0.5 mg/liter (500 ppm).
Pike (Esox luci-us) were somewhat less sensitive, with  the first deaths
occurring at 0.5 mg/liter  (500 ppm) and all the pike killed at two mg/
liter  (2000 ppm) (Luedemann and Neumann 1961).  The 48 hour EC - (ef-
fective median concentration) of diazinon was 170 ppb  in rainbow trout
and 86 ppb in bluegills at 24°C (Pimentel 1971).  The  LD__ for bull-
frogs was over 2000 mg/kg  (Tucker and Crabtree 1970).
Birds—The oral LD   of diazinon was 3.5 mg/kg in young mallards and
4.3 mg/kg in pheasants (Tucker and Crabtree 1970).  For redwinged black-
birds and starlings, the acute oral LD^_ was 110 mg/kg and 2.0 mg/kg
respectively (Schafer 1972).  The five day dietary LC,.- in bobwhites,
pheasants, Japanese quail, and mallards was 245 ppm, 244 ppm, 47 ppm,
and 191 ppm, respectively  (Heath et al. 1972).  Diazinon was terato-
genic in chicks (Green 1970) and reduced hatchability  at levels of one
ppm (Sauter and Steel 1972):  egg production declined  at 180 ppm (Von-
dell 1958).
Mammals—The acute oral LD_n of diazinon in rats is variously given as
75 mg/kg in females and 108 mg/kg in males (Gaines 1968, Pimentel 1971):
150 to 220 mg/kg (Schafer 1972) or even 300 to 600 mg/kg (Jones et al.
                                  473
-------
1968).  Formulated diazinon which had decomposed during storage was 30
times as toxic to humans and to cattle as freshly formulated diazinon
because of the formation of tetraethylmonothiopyrophosphate (Mello et
all. 1972).  Like all organophosphates, the oxon of diazinon is a chol-
inesterase inhibitor; its toxicology was described by Gysin and Margot
(1958) and the toxicology of organophosphates including diazinon has
been reviewed recently (Eto 1974).
At 100 to 200 mg/kg, diazinon was both toxic to pregnant rats and ter-
atogenic to their fetuses (Kimbrough and Gaines 1968).  Seven mg/kg
and 30 mg/kg of diazinon did not produce congenital malformations in
rabbits, and 0.125 and 0.25 mg/kg were not teratogenic in hamsters
(Robens 1969).  A mutagenic effect  of diazinon on human peripheral
leukocytes in culture has been reported (Tsoneva-Maneva et_ al. 1969) .
Conclusions-
Neither the persistence of diazinon itself nor its effects on soil pro-
cesses and soil microorganisms is extreme.  Nevertheless, there is no
conclusive evidence for the decomposition of diazinon to naturally
occurring substances, and data are  lacking on the persistence, trans-
port and effects of 2-isopropyl-4-methyl-6-hydroxypyrimidine in soil.
Therefore, large-scale soil disposal of diazinon in the absence of
further information is not recommended.
                                  474
-------
Disulfoton and Phorate
Disulfoton is the common name for 0, (9-diethyl S'-2-(ethylthio)ethylphos-
phorodithioate, introduced by Farbenfabriken Bayer AG in 1956 under
the trade names Di-Syston and Dithio-Systox as a systemic insecticide
and acaricide.  It is made by the interaction of the sodium salt of
030-diethyl hydrogen phosphorodithioate with 3-chloroethyl thioethyl
ether (Martin 1968) .  The pure compound is a colorless oil with a char-
acteristic odor, a vapor pressure of 1.8 mm mercury at 20 C, and a
water solubility of 25 ppm at 20°C.  Its boiling point is 62°C at 0.01
mm mercury, and it is readily soluble in most organic solvents.  The
technical product is a dark yellow oil.  Formulations include granules
and impregnation on activated carbon.
Phorate is the common name for G^O-diethyl £'-(ethylthio)methyl phos-
phorodithioate, introduced by the American Cyanamid Company as Thimet
in 195A.  It is a systemic insecticide used primarily to protect seed-
lings from sap-feeding insects.  Phorate is made by the reaction of
0,0-diethyl hydrogen phosphorodithioate with formaldehyde, followed by
the addition of ethyl mercaptan.  It is a clear liquid with a boiling
point of 118 to 120 C at 0.8 mm mercury, a freezing point below -15 C,
                                -4                o
and a vapor pressure of 8.4 x 10  mm mercury at 20 C.  Its solubility
in water is 50 ppm at room temperature and it is readily miscible with
vegetable oils and xylene, as well as with carbon tetrachloride and
dioxane.  It is formulated as an emulsifiable concentrate, dusts and
granules.
Degradation-
Biological—Data on metabolic products of disulfoton and phorate are
summarized in Table 74.  The primary degradative pathways of disulfo-
ton and phorate proceed via their sulfoxides to their sulfones, lead-
ing to an increase in the anticholinesterase activity (Metcalf et al.
                                  475
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476
-------
1957, Fukuto and Metcalf 1969).  Getzin and Shanks  (1970) analyzed the
degradation of phorate and its oxygen analog in soil, and noted that
phorate is converted to phorate sulfoxide and then  to its sulfone; in
Sultan silt loam, conversion of phorate sulfoxide to phorate was also
observed.  In a plant-soil model ecosystem, corn plants contained only
metabolites of phorate even though the soil still contained unaltered
phorate.  Corn roots as well as soil contained phorate sulfone and phor-
ate  sulfoxide, while the leaves of the plants contained phoratoxon
sulfoxide and phoratoxon sulfone (Lichtenstein et al. 1974).  When
phorate was applied to soil in granular bands under field conditions,
the major metabolite was phorate sulfone when the level of treatment
was five Ibs/A (5.60 kg/ha), but phorate sulfoxide when the level of
treatment was one Ib/A (1.12 kg/ha).  The oxygen analog of phorate was
not found in submerged soils (Kawamori et_ al. 1971b) .
Almost no degradation of either phorate or disulfoton occurred in soil
in a 60 day period in summer, and degradation was significantly greater
between October and April than in the summer; temperature played a
greater role in determining the rate of degradation than did soil type.
In the winter, disulfoton was degraded more rapidly than phorate; in
summer, too little degradation took place to distinguish differences.
The soil type and temperature effects interacted, with degradation be-
ing more rapid in loamy sand in the winter and in silt loam in the sum-
mer (Menzer et al. 1970).  Takase and co-workers (1972) examined the
degradation of disulfoton in several soils.  Metabolism was more rapid
in all soils under flooded (anaerobic) than under upland (aerobic) con-
ditions, microbial oxidation was considered the major route of degra-
dation, and little breakdown occurred in sterile soil.  A later study
of the breakdown of disulfoton in sterile and glucose-amended soil was
considered to provide evidence against microbial oxidation (Takase and
Nakamura 1974).
Whether the most rapid route of degradation in the field is chemical or
biological has never been proven, but disulfoton is readily degraded by
                                 477
-------
microorganisms, at least under laboratory conditions:  most fungi
(among twenty isolates tested) were able to use disulfoton as their
sole source of carbon, as were most of the ten cultures of Streptomy-
cetes tested.  Aspevgi,t1us f1avwny Ee1mint'kospovi.wn3 and two StTepto-
myaes species were able to grow with disulfoton as their only source
of carbon (Bhaskaran et al. 1973),
In rats, the excreted metabolites of disulfoton were diethylphosphoro-
thioic acid, diethyl phosphoric acid, and two unknown compounds, while
phosphoric acid and traces of diethylphosphorodithioic acid were found
in the rats' urine.  Intermediates in the rats' livers, 30 minutes
after intraperitoneal injection of 10.5 mg/kg of disulfoton, included
disulfoton sulfoxide and sulfone  (Bull 1965).
Chemical and physical—Di-Syston applied to fertilizer, particularly
superphosphates, decomposes as a result of catalytic oxidation  (Ibra-
him et al. 1969).  When disulfoton and phorate were exposed to one to
four Mrad of cobalt-60 gamma-irradiation, the corresponding sulfoxides
and sulfones were found in most samples; the sulfoxide of the oxygen
analog and the sulfone of the oxygen analog were found only after treat-
ment with the full four Mrad dose.  Irradiation increased the inhibi-
tion of beef liver carboxylesterases by the pesticides, suggesting
that the radiation-induced degradation consisted mostly of activation
(Grant et al. 1969) .
Transport-
Within soil—Phorate was less mobile than diazinon, and less mobile in
degraded chernozem and in black marsh soil than in brown forest soil
(Ostojic _e_^ al_. 1972).  McCarty and King (1966) considered disulfoton
to move rapidly in soil-water systems.  Harris (1969b) compared the mo-
bility of pesticides in 17.8 cm soil columns and found phorate and di-
sulfoton to be only slightly mobile, albeit more mobile than the chlor-
inated hydrocarbon insecticides.  No data were available on the trans-
port of the metabolites of disulfoton or phorate within soil.
                                   478
-------
Between soil and water—In addition to transport through soil into
water, transport on soil particles (washoff) can be a means of pesti-
cide transport into streams and lakes.  Kawamori and co-workers  (1971a)
noted that disulfoton adsorbs more readily to silty clay loam than to
clay loam, and least readily to alluvial loamy sand.  They concluded
that the high rate of recovery was due to adsorption on the organic
rather than on the clay fraction.  Both compounds were most readily ad-
sorbed to mineral soils (Harris and Hitchon 1970) and to silty loam
and clay soils (Bhirud and Pitre 1972) when the soils were dry.  Soil-C
adsorbed disulfoton could not be desorbed if soil had dried in the in-
terim (Graham-Bryce 1967) .  Transport of newly desorbed disulfoton or
phorate in runoff remains a possibility, but no data are available to
assess its plausibility.
Volatilization—Burns (1971) considered the 41 percent loss of phorate
from sandy soil within the first three days after application to be
due largely to volatilization.  Losses from clays and loams were much
smaller.
Into organisms—Both phorate and disulfoton are systemic insecticides,
readily taken up by plants.  Soil treated with two pounds per acre (2.24
kg/ha) of either phorate or disulfoton resulted in excessively high
levels in spinach after 5.5 months; both parent compounds, their sul-
foxides, their sulfones, and the sulfoxides of their oxygen analogs
were found in the spinach (Menzer and Ditman 1968) .  When soil was
treated with 30 kg/ha of five percent disulfoton granules (Solvirex)
17 days after potatoes were planted, potato tubers contained 0.04 to
0.11 ppm at harvest time (Trojanowski et_ al^. 1967).  Masuda and Kana-
zawa (1972) detected 0.18 ppm disulfoton in unpolished rice 53 days
after soil was treated with 2.5 kg/ha.  The residual levels of disul-
foton in vegetables grown on treated soil were greatest in carrots,
intermediate in Chinese cabbage, and lowest in turnips.  Carrots, rice,
and soil contained relatively more disulfoton sulfone than disulfoton
sulfoxide (Masuda and Kanazawa 1972).
                                   479
-------
When phorate was applied to soil or sand, only metabolites were found
in the corn grown on the soil; oxidation appeared to occur in the plant,
not in the soil.  Root residues were 2.5 to five times as great in
plants grown on sand as in plants grown on agricultural soils, but leaf
residues were the same regardless of the soil type (Lichtenstein et al.
1974) .  Sorghum retained no residues of disulfoton 85 days after soil
treatment (Singh et_ al_. 1972), but carrots contained phorate sulfone
even in the second growing season after soil treatment (Lichtenstein
et al. 1973).  Potatoes contained residues only in the growing season
during which soil had been treated (Batora et al. 1967).
Persistence-
The available data on persistence of disulfoton and phorate in soil
are summarized in Tables 75 and 76.  Persistence differs widely not
only because of differing test conditions between experiments, but also
because different assays were used.  Bioassays dominate the literature
on phorate and disulfoton; the data are therefore skewed to include
insecticidal metabolites of the applied insecticides.  Persistent but
non-insecticidal metabolites have not been considered to any great ex-
tent in studies available to date.  Among the possible factors decreas-
ing the measured persistence of phorate and disulfoton are losses due
to volatilization of sprayed insecticides and adsorption to soil.  The
latter almost certainly serves to prolong soil retention even while
decreasing persistence as measured by bioassays.
Effects on Non-Target Species-
Microorganisms—The effects of phorate and disulfoton on soil micro-
organisms and soil invertebrates are summarized in Tables 77 and 78.
Cowley and Lichtenstein (1970) observed inhibition in 13 of 17 fungal
cultures treated with 40 yg/ml (40 ppm) of phorate, but in a fescue
meadow treated with agricultural levels of phorate, both bacteria and
fungi were stimulated for most of one year (Malone and Reichle 1973) .
                                   480
-------


















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The latter report suggests that phorate decreased the populations of
soil arthropods, with secondary increases in bacteria and fungi.
Sreenivasula and Rangaswami  (1973) reported the stimulation of almost
all soil microorganisms by phorate and disulfoton, but noted that, as
the incubation progressed, gram-positive bacteria were displaced by
gram-negative bacteria.  Laygo and Schulz (1963) reported recovery of
soil microfaunal populations within nine days of phorate application
even though the compound itself persisted more than 23 days.
Invertebrates—Phorate decreased populations of Collembola and of soil
arthropods other than mites  (Malone and Reichle 1973), and decreased
total numbers of mites for more than nine months if applied at 4.5 kg/
ha (Edwards and Thompson 1973).  Organophosphorus insecticides reduced
the number and biomass of soil invertebrates less than did aldrin or
dieldrin, but phorate and disulfoton significantly decreased populations
of parasitic mites and paurapods, and increased populations of trombi-
diform mites, oribatid mites, and springtails.  Phorate, but not disul-
foton, significantly decreased earthworm populations (Edwards et al.
1969, Edwards and Thompson 1973).
The LD__ of phorate to bees was 0.004 percent (40 ppm) (Johansen 1961).
The nectar of fuchsia and nasturtiums watered with 25 mg phorate was
not toxic to honeybees and the acute oral LD,.- of disulfoton and phor-
ate to honeybees was reported as greater than 20 yg/bee and 0.44 yg/bee,
respectively (Lord et^ al. 1968).
Disulfoton was toxic to aquatic insects at levels between 0.0082 mg/
liter (stone fly, AoTonewcia paaifioa) and 0.24 mg/liter (freshwater
shrimp, Gcamarus loeustr-is)  (Gaufin et^ al. 1965).  Disulfoton decreased
survival and affected development of the eggs of both oysters (Crasso-
strea. virginiaa) and clams (MevaencafLa meraenai"ia) at levels of one ppm
or more (Davis and Hidu 1969).
                                  485
-------
Plants—At 60 kg/ha, disulfoton caused an initial delay in plant growth,
followed by enhanced growth after 30 days (Kobayashi and Katsura 1968).
A.t ten ppm, soil-incorporated disulfoton stimulated growth of bean and
corn plants for six weeks, but at 100 ppm, growth inhibition occurred.
Disulfoton at 100 ppm also increased the levels of nitrogen, phosphorus,
potassium, calcium, and magnesium; and decreased levels of iron, cop-
per, aluminum and zinc in the treated plants  (Cole et^ _al. 1968).  Di-
sulfoton inhibited the metabolism of linuron and dicamba in leafy tis-
sues (Chang et al. 1971).  Phytotoxicity between dalapon and either di-
sulfoton or phorate was additive, indicating no interaction between
the herbicide and either insecticide (Nash 1967).
Fish and amphibians—Phorate at agricultural levels was toxic to carp
(Lilly et_ al. 1969) .  The 96 hour median tolerance limit (TO for di-
sulfoton was 0.063 ppm in bluegills (Lepomis maerochirus'), 0.25 ppm in
guppies (Lebi-stes reti-culatus), 3.7 ppm in fathead minnows (Pi-mephales
promelas), and 6.5 ppm in goldfish (Carassius auratus)  (Pickering et
al. 1962).
Birds—The acute oral LD   of disulfoton was greater than 32 mg/kg in
starlings, and was 3.2 mg/kg in redwinged blackbirds; for phorate, the
LD,-0 was 7.5 mg/kg in starlings and 1.0 mg/kg in redwinged blackbirds
(Schafer 1972).  The dietary LC_n of disulfoton when birds were fed
treated feed for three days was 333 ppm in Japanese quail (Cotumix
ooturnix) , 715 ppm in bobwhite (Colinus wi-rg-inianus) , 634 ppm in phea-
sants, and 510 ppm in mallards (Anas platyrhynchos) (Heath et_ al_. 1972).
Phorate (as Thimet) injected into hens' eggs at two ppm on the 10th day
of incubation decreased the hatchability from 89.7 to 27.5 percent,
increased the thyroid size of the chicks, and was teratogenic (Richert
and Prahlad 1972).
Mammals—The acute oral LD   of phorate in rats was reported to be two
to three mg/kg (Jones et al. 1968); for disulfoton, an LDcn of 12.5
                      	       '                      ju
                                   486
-------
mg/kg is cited by Pimentel  (1971), while Jones et al.  (1968) cited
4 mg/kg.  Both compounds were toxic when applied to rats' skins, with
a dermal I&c.n °f 7® to 300 rag/kg cited for phorate and 50 mg/kg for di-
sulfoton (Jones et al. 1968).
Conclusions-
Most of the data on the persistence of phorate and disulfoton in soil
are based on persistence of bioactivity, rather than on chemical per-
sistence.  Moreover, essentially no data on the transport of either
compound in soil, into water, or into air are available.  Therefore,
no conclusions on the feasibility of soil disposal of either phorate
or disulfoton can be drawn.
                                  487
-------
Az Inpho sme t hy 1
Azinphosmethyl is the common name for 0, 0-dimethyl  £-(4-0X0-1,2,3-
benzo-triazin-3(4H)-61)methyl  phosphorodithioate.  It is made by the
interaction of ^-chloromethylbenzazimide with Ot 0-dimethyl hydrogen
phosphorodithioate in the presence of a base.  A non-systemic insecti-
cide and acaricide, azinphosmethyl was introduced by Farbenfabriken
Bayer AG in 1953 and is known under the trade names Guthion and Gusa-
thion.  Azinphosmethyl forms white crystals with a melting point of
73 to 74°C.  It is very slightly soluble in water (3.3 ppm at 25°C)
and is soluble in most organic solvents.  It is unstable above 200°C.
Degradation-
Biological — Microbial degradation of azinphosmethyl was presumed to ac-
count for the faster loss of azinphosmethyl from natural than from
sterilized soil, but non-biological factors appeared to predominate
(Yaron e_t^ al_. 1974a, see below).  In mice, the microsomal and soluble
fractions of liver cells were most active in converting azinphosmethyl
to its oxygen analog, and also in degrading it to dimethyl phosphoric
acid and dimethyl phosphorothioic acid (Motoyama 1972) .
Chemical — Yaron and co-workers (1974a) analyzed the kinetics of
phosmethyl loss from soil and concluded that both biological and chem-
ical mechanisms contributed to its degradation.  A lag phase was obser-
ved in all soils; subsequent degradation essentially corresponded to
first-order kinetics.  Degradation was most rapid, and the lag phase
least pronounced, in moist, unsterilized soil at warm temperatures.
Table 79 shows the length of time required for the loss of 50 percent
of the azinphosmethyl applied to a silty, loamy, loessial sierozem.
Moisture affected the rate of degradation more than did microbial acti-
vity, and temperature was extremely important in determining the half-
life of azinphosmethyl within each soil/moisture combination.
                                 488
-------
Table 79.  NUMBER OF DAYS REQUIRED FOR 50% LOSS OF AZINPHOSMETHYL
    FROM SOIL AT THREE TEMPERATURES AND TWO LEVELS OF MOISTURE
                   (AFTER YARON ET_ AL. 1974a)

 ~~Sterile soilNatural soil
 Temperature       	            	
    (°C)	Dry	Wet	Dry	Wet
      6            484            88            484            64
     25            135            29             88            13
     40             36             6             32             5
                                489
-------
                                      o
Photolytic—Ultraviolet light at 2537 A  decomposed azinphosmethyl la-
beled at the carboxyl carbon.  The degradation products were:  benza-
zimide, anthranilic acid, methyl benzazimide sulfide, ff-methyl benzazi-
mide, and an unidentified water-soluble compound.  None of the products
was insecticidal.  Degradation proceeded only in the light, and was
more rapid in water at high pH than on glass.  In water at pH 10, 18
percent of the metabolites were water-soluble, while at pH 11, 97 per-
cent were water-soluble.  Azinphosmethyl was stable in water between
pH 6 and pH 9 (Liang and Lichtenstein 1972).
Transport-
Through soil—Eight years after an undiluted (18.1 percent) emulsibiable
concentrate of azinphosmethyl was applied to soil, no residues were de-
tected below 37.5 cm in sandy loam soil (Staiff et_ a!U 1975).  Yaron et_
al. (1974b) concluded that azinphosmethyl did not leach deeply into
soil, and also that its leaching was unaffected by the amount of irri-
gation.
Volatilization—Azinphosmethyl was less readily volatilized from leaves
or from soil than were diazinon, parathion, and several organochlorine
insecticides (Lichtenstein and Schulz 1970).  Its volatilization from
leaves was reportedly not affected by high temperatures (Hightower and
Martin 1958).
Into organisms—Azinphosmethyl applied to an irrigated field at normal
agricultural levels resulted in residues in potato peels (Yaron et al.
1974b) .
Persistence-
Staiff and co-workers (1975) assessed the persistence of several for-
mulations and several levels of azinphosmethyl in sandy loam soil over
an eight year period.  The soil pH ranged from 6.6 to 7.8, and rainfall
averaged 25 cm per year.  Their data are summarized in Table 80.  They
concluded that soil contamination by undiluted azinphosmethyl remained
                                   490
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Table 80.  RESIDUES OF AZINPHOSMETHYL IN SOIL AFTER CONTAMINATION
      WITH UNDILUTED  (18.1%) AND DILUTED (0.045%) EMULSIFIED
       CONCENTRATE SOLUTIONS AND DILUTED SOLUTIONS (0.045%)
                        OF WETTABLE POWDER.
Contaminant;
soil stratum
EC-7: 18.1%;
0-2.5 cm
2.5-7.5 cm
EC-7: 0.045%
0-2.5 cm
2.5-7.5
WP-7: 0.045%
0-2.5 cm
2.5-7.5 cm
Time
1 day

49,946 ppm
30,488 ppm

354 ppm
23 ppm

276.8 ppm
107.0 ppm
after application
4 years

6,075 ppm
7,662 ppm

1 . 5 ppm
1 . 3 ppm

2.0 ppm
2 . 2 ppm

8 years

850 ppm
967 ppm

Nl£7
Nl£7

ND
ND
aj Emulsifiable concentrate
W Not detected
cj Wet table powder
                                491
-------
a significant hazard for at least four years.
The soil residues in the top 7.5 centimeters four years after the soil
was contaminated with diluted azinphosmethyl at 0.045 percent (450 ppm)
represented 1.6 percent of the initial residues, or a loss of 24.6 per-
cent per year while the undiluted emulsibiable concentrate left resi-
dues representing 2.5 percent of the initial residues after eight years,
corresponding to a loss of 12.2 percent per year.  It was suggested
that high concentrations of azinphosmethyl strongly inhibit soil micro-
organisms, resulting in slower degradation of the pesticide.
Soil-applied azinphosmethyl decomposed rapidly in Georgia cotton-grow-
ing soil, but traces could be detected to the end of the third year
(Roberts et_ al. 1962).  At agricultural levels in an irrigated field,
azinphosmethyl reportedly disappeared within thirty days regardless of
the amount of irrigation (Yaron et_ al. 1974).  Ruhr et_ al. (1974) also
reported that three Ibs/A (3.36 kg/ha or 6 ppm) of azinphosmethyl de-
creased to 1.6 ppm within thirty days in one orchard; essentially com-
plete dissipation occurred within sixty days in a second orchard.
In water, azinphosmethyl has a half-life of about thirty days at pH 9.0,
but of less than seven days at pH 9.5, when the temperature is at 25 C;
at 45 C and pH 9.5, the half-life decreased to less than one day (Heuer
et_ al. 1974).  In comparing the persistence of water emulsion sprays
with that of low-volume sprays on oat plants, Dorough and Randolph (1967)
found that azinphosmethyl persisted longer as a low-volume spray (21
days) than as a water emulsion spray (Seven days).
Effects on Non-Target Species-
Microorganisms—Azinphosmethyl reportedly had no effect on yeast res-
piration of fermentation at concentrations ranging between 2 x 10   M
and 2 x 10~3M (Eder 1963) .  Staif f et_ al^. (1975) considered it proba-
ble that azinphosmethyl at high levels partially sterilized the soil,
hindering its own degradation.
                                   492
-------
Plants—No reports of phytotoxicity were found for azinphosmethyl, but
it has been reported to inhibit photosynthesis in the leaves of Red
Delicious apples  (Heinicke and Foot 1966).
Invertebrates—Azinphosmethyl is more highly toxic to earthworms  (Eis-
enia sp.) than malathion or the organochlorines BHC, chlordane, hepta-
chlor, aldrin and dieldrin (Hopkins and Kirk 1957).  It is highly toxic
to honeybees (Anderson and Atkins 1958, Anonymous 1974).  When ladybird
beetles were immersed in azinphosmethyl at concentrations of 0.5 lb/100
gallons, 35 to 65 percent survived (Colburn and Asquith 1973).
Fish and amphibians—The 96 hour TL.. of young salmonids to azinphos-
methyl was 0.58 ppb (0.0006 ppm) for rainbow trout, 4.2 ppb (0.0042
ppm) for coho salmon, and 4.3 ppb (0.0043 ppm) for chinook salmon
(Katz 1961).  Only 13 percent of carp embryos exposed to one part per
million survived to hatch; 0.1 ppm did not increase embryonic mortali-
ty, but resulted in 100 percent mortality of all fry within 48 hours
after eclosion (Malone and Blaylock 1970).  The toxicity of azinphos-
methyl to bluegills and to rainbow trout increased with increasing tem-
peratures (Macek et^ al. 1969).  At levels used for controlling mosquito
larvae, azinphosmethyl was reportedly not toxic to the mosquitofish
(Gambus-La) or to pollywogs (Mulla et al. 1963).
Birds—The acute oral LDcn of azinphosmethyl was 125 to 150 mg/kg in
mallards (Keith and Mulla 1966) and 277.2 mg/kg in 10 to 12 day old
chickens (Sherman et al. 1967) .  The LC   of azinphosmethyl to baby
chicks was 1197 ppm, but levels above 300 ppm decreased growth rates
within one week (Steve £t_ a.l_. 1961).  Injection of one mg azinphosmethyl
into chicken eggs was teratogenic (Upshall et al. 1968).  Chickens fed
40 mg/kg azinphosmethyl developed leg weakness (Gaines 1969).
Mammals—The acute oral LD5Q of azinphosmethyl in rats is 15 mg/kg (Eto
1974).  No data were available on the carcinogenicity, mutagenicity,
teratogenicity, or other reproductive effects of azinphosmethyl.
                                   493
-------
Conclusions-
Despite its apparently rapid dissipation in soil, and its consequently
minimal leaching, the feasibility of disposing of azinphosmethyl in
soil is not demonstrated by the data.  Staiff and co-workers (1975)
have indicated a tendency for higher levels of soil contamination to
resist degradation; no contrary data are available.  There is plenti-
ful evidence, however, that temperature and moisture exert a strong
effect on the rate of azinphosmethyl degradation.  Therefore, the
least objectionable site for soil disposal of azinphosmethyl wastes
would be a moist, semitropical soil.  Since wettable powders appear to
degrade more quickly, but leach more readily than emulsifiable concen-
trates, no conclusions concerning relative risks of different formula-
tions can be drawn.
                                  494
-------
References
Ackermann, H.; 1974.  Transfer of organophosphorous insecticides to the
  embryo.  Formation of PO derivatives and development of toxic symp-
  toms.  Tagungsber., Akad. Landwirtschaftswiss. D.D.R. 126:23-29.
  (Chem. Abstr. 83:73040m, 1975).
Ackermann, H. and R. Engst; 1970.  Presence of organophosphate insec-
  ticides in  the fetus.  Arch.Toxicol. 26:17-22. (Chem. Abstr. 72:
  89196a, 1970).
Ahmed, N. and F. 0. Morrison; 1972.  Longevity of residues of four or-
  ganophosphate insecticides in soil.  Phytoprotection 53:71-74.
Alamanni, U.  and A. M. Cosseddu; 1969.  Protracted administration of
  parathion in lactating sheep and analytical findings on the milk
  produced.   Boll. Lab. Chim. Prov. 20:492-505. (Chem. Abstr. 73:13501w,
  1970).
Albright, R., N. Johnson, T. W. Sanderson, R. M. Farb, R. Melton, L.
  Fisher, G.  R. Wells, W. R. Parsons, V. C. Scott, J. L. Speake, J. R.
  Stallworth, B. G. Moore and A. W. Hayes; 1974.  Pesticide residues
  in the top  soil of five west Alabama counties.  Bull. Environ. Con-
  tarn. Toxicol. 12:378-384.
Alessandrini, M. E. and V. Amormino; 1954.  Comparative determinations
  of the volatility of some organic phosphorus insecticides.  Intern.
  Symposium on Control of Insect Vectors of Disease.  1954:93-96.
  (Chem. Abstr. 49:l6309c, 1955).
Alexander, M.; 1972.  in:  Environmental Toxicology of Pesticides> pp.
  365-383.; F. Matsumura, G. M. Boush and T. Misato, eds.; Academic
  Press, N. Y.
Anderson, L. D. and E. L. Atkins, Jr.; 1958.  Toxicity of pesticides
  to honey bees in laboratory and field tests in southern California,
  1955-1956.  J. Econ. Entomol. 51:103-108.
Anonymous; 1974.  Entomology fact sheet:  Check list of insecticides.
                                  495
-------
  111. Nat. His. Survey and Coop. Ext. Serv. U.I. College of Agr.
  //NHE-90.
Appert, J.; 1952.  Influence of tropical climate on the persistence
  of organic insecticides.  Ann. Centre Recherches agron. Bambey au
  Sdndgal 1951, Ministere France outre-mer, Direction agr. e"levage et
  for§ts, Bull, Agron. No. 7, 204-208. (Chem. Abstr. 47:5062c, 1953).
Archer, T. E.; 1971.  Malathion  £>-0-dimethyl S-l,2-di(ethoxy-carbamyl)-
  ethyl phosphorodithioatej  residues on ladino clover seed screenings
  exposed to ultraviolet irradiation.  Bull. Environ. Contam. Toxicol.
  6:142-143.
Arsenault, A. L. and M. A. Gibson; 1974.  Histogenesis of the islets
  of Langerhans in malathion-treated chick embryos.  Can. J. Zool.
  52:1541-1544.
Arterberry, J. D., W. F. Durham, J. W. Elliott and H. R. Wolfe; 1961.
  Exposure to parathion.  Arch. Environmental Health 3:476-485.
Augustinsson, K. B. and G. Jonsson; 1957.  Biochemical studies on the
  degradation products of diazinon.  Experientia 13:438-439.
Baker, R. D. and H. P. Applegate; 1970.  Effect of temperature and ul-
  traviolet radiation on the persistence of methyl parathion and DDT
  in soils.  Agron. J. 62:509-512.
Bartsch, E.; 1974.  Diazinon.  II. Residues in plants, soil, and water.
  Residue Reviews 51:37-68.
Batora, V., J. Kovacicova and J. Moravcik; 1967.  Disulfoton residues
  in potatoes and soil after application of granulated preparations.
  Agrochemia (Bratislava) 7:161-163. (Chem. Abstr. 70:105210s, 1969).
Bender, M. E.; 1969.  Uptake and retention of malathion by the carp.
  Progr. Fish Cult. 31:155-159.
Bhaskaran, R., D. Kandasamy, G. Oblisami and Tr. Subramaniam; 1973.
  Utilization of disyston as carbon and phosphorus sources by soil
  microflora.  Curr. Sci. 42:835-836.  (Chem. Abstr. 80:116867u, 1974).
Bhirud, K. M. and H. N. Pitre; 1972.   Influence of soil class and soil
  moisture on bioactivity of carbofuran and disulfoton in corn in
                                  496
-------
  greenhouse tests.  Relation to leafhopper vector control and corn
  smut disease incidence.  J. Econ. Entomol. 65:324-329.
Billard, R. , P. DeKinkelin and A. M. Escaffre; 1970.  Sterilization
  of the testicles of guppies with nonlethal doses of parathion.  Ann.
  Hydrobiol. 1:91-99. (Chem. Abstr. 74:110802y, 1971).
Bourquin, A. W. ; 1975.  Microbial-malathion interaction in artificial
  salt-marsh ecosystems, effect and degradation.  EPA Ecological Re-
  search Series EPA 75-035.
Boush, G. M. and F. Matsumura; 1967.  Insecticidal degradation by
  Pseudomonas meolphthora, the bacterial symbiote of the apple maggot.
  J. Econ. Entomol. 60:918-920.
Bowman, B. T., R. S. Adams, Jr., and S. W. Fenton; 1970.  Effect of
  water on malathion adsorption on five montmorillonite systems.  J.
  Agr. Food Chem. 18:723-727.
Bro-Rasmussen, F., E. Noeddegaard and K. Voldum-Clausen; 1968.  Degra-
  dation of diazinon in soil.  J. Sci. Food Agr. 19:278-281.
Bro-R.asmussen, F., K. Orboek, K. Voldum-Clausen and E. Noeddegaard; 1969.
  Residues of five organophosphate insecticides in carrots, rutabagas,
  cabbage, cauliflower, and onions.  Tidsskr. Planteaul. 73:382-393.
  (Chem. Abstr. 72:77562d, 1970).
Brunson, M. H. and L. Koblitsky; 1952.  Parathion, DDT, and EPN depo-
  sits on peach foliage and fruit.  J. Econ. Entomol. 45:953-957.
Bull, D. L.; 1965.  Metabolism of Di-syston by insects, isolated cot-
  ton leaves, and rats.  J. Econ. Entomol. 58:249-254.
Burke, W. D. and D. F. Ferguson; 1969.  Toxicities of four insecti-
  cides to resistant and susceptible mosquitofish in static and flow-
  ing solutions.  Mosquito News 29•96-101.
Burkhardt, C. C. and M. L. Fairchild; 1967a.  Toxicity of insecticides
  to house crickets and bioassay of treated soils in the laboratory.
  J. Econ. Entomol. 60:1496-1503.
Burns, R. G.; 1971.  Loss of phosdrin and phorate insecticides from a
  range of soil types.  Bull. Environ. Contam. Toxicol. 6:316-321.
                                   497
-------
Butler, G. L. , T. R. Deason and J. C. O'Kelley; 1975.  Loss of five
  pesticides from cultures of twenty-one planktonic algae.  Bull. En-
  viron. Contain. Toxicol. 13-149-152.
Cabejszek, I. and J. Maleszevska: 1970.  Effect of methyl parathion
  and thiometon on oxygen consumption by aquatic organisms.  Rocz.
  Panstw. Zakl. Hig. 21:1-6. (Chera. Abstr. 73:44263z, 1970).
Capriotti, A. and A. Martini; 1959.  Effect of some modern weed killers,
  'insecticides and fungicides on the soil microflora.  II. Insecti-
  cides.  Ann. Fac. Agrar. Univ. Studi. Perugia 14:77-94. (Chem.
  Abstr. 57:10285d, 1962).
Carlo, C. P., D. Ashdown and TT. G. Keller; 1952.  Persistence of para-
  thion, toxaphene, and methoxychlor in soil.  Oklahoma Agr. Expt. Sta.
  Tech. Bull. No. T-42'11 pp. (Chem. Abstr. 46:3707b, 1952).
Chang, P., L. W. Smith and G. P. Stephenson; 1971.  Insecticide inhi-
  bition of herbicide metabolism in leaf tissues.  J. Agr. Food Chem.
  19:1183-1186.
Chapman, S. K. and K. C. Leibman; 1971.  Effects of chlordane, DDT and
  3-raethylchloranthrene upon the metabolism and toxicity of diethyl-4-
  nitrophenylphosphorothioate (parathion).  Toxicol. Appl. T>harmacol.
  18:977-987.
Chopra, S. L. and K. C. Girdhar; 1971.  Persistence of malathion, 5-1,
  2bis(ethoxycarboxyl)ethyl-$,0-dimethyl phosphorodithioate, in Pun-
  jab soils.  Indian J. Appl. Chem. 34 (5) .-201-207. (Chem. Abstr. 77:
  110554f, 1972).
Chopra, S. L. and F. C. Khullar; 1971.  Degradation of parathion in
  soils.  J. Indian Soc. Soil Sci. 19:79-85.
Chopra, S. L. , ?-T. Das and B. Das; 1970.  Adsorption and leaching of
  parathion  (030-diethyl 0-p-nitrophenyl phosphorothioate) on soils
  and effect of various physical factors on adsorption.  J. Indian
  Soc. Soil  Sci. 18:437-446.
Christie, A. E.r 1969.  Effects of insecticides on algae.  Water Sew-
  age Works  116:172-176.
                                   498
-------
Clinch, P. G.; 1969.  Laboratory determination of the residual fumi-
  gant toxicity to honeybees of insecticide sprays on white clover  (Tri-
  foliwn repens).  N. Z. J. Agr. Res. 12:162-170.
Coffin, D. E. and W. P. McKinley: 1964.  The metabolism and persis-
  tence of systox, diazinon, and phosdrin on field-sprayed lettuce.  J.
  Assoc. Office Agr. Chemists 47:632-640.
Cohen, S. D. and S. D. Murphy; 1974.  Simplified bioassay for organo-
  phosphate detoxification and interactions.  Toxicol. Appl. Pharmacol.
  27:537-550.
Colburn, R. and D. Asquith; 1973.  Tolerance of Stethories punctim
  adults and larvae to various pesticides.  J. Econ. Entomol. 66:961-
  962.
Cole, !!., D. Mackenzie, C. B. Smith and E. L. Bergman; 1968.  Influence
  of various soil-incorporated fungicides and nematocides on macro- and
  microelement constituents of Zea mays and Pkaseolus vulgaris.   Bull.
  Environ. Contain. Toxicol. 3:116-126.
Cook, J. W., J. R. Blake and M. W. Williams; 1957.  The enzymic hydro-
  lysis of malathion and its inhibition by EPN and other organic phos-
  phorous compounds.  J. Assoc. Office. Agr. Chemists 40:664-665.
Cook, J. W., J. R. Blake, G. Yip and M. Williams; 1958.  Malathionase.
  I. Activity and inhibition.  J. Assoc. Offic. Agr. Chemists 41G99-
  407.
Cowert, R. P., F. L. Bonner and E. A. Epps, Jr.; 1971.  Rate of hydro-
  lysis of seven organophosphate pesticides.  Bull. Environ. Contam.
  Toxicol. 6:231-234.
Cowley, G. T. and E. P. Lichtenstein; 1970.  Growth inhibition of soil
  fungi by insecticides and annulment of inhibition by yeast extract
  or nitrogenous nutrients.  J. Gen. Microbiol. 62:27-34.
Crosby, D. G.; 1969.  The nonmetabolic decomposition of pesticides.
  Ann. N.Y. Acad. Sci. 160:82-96.
Danilov, V. B.; 1968.  Hygienic estimate of the contamination of the
  atmosphere with carbophos used in Uzbekistan agricultures.  Med.  Zh.
  Uzb. 1968:23-26. (Chem. Abstr. 70:56688t, 1969).
                                  499
-------
DaSilva, E. J., L. E. Henriksson and E. Henriksson; 1975.  Effect of
  pesticides on blue-green algae and nitrogen fixation.  Arch. Envi-
  ron. Contam. Toxicol. 3:193-204.
Dauterman, W. C. and A. R. Main; 1966.  Relationship between acute
  toxicity and -In vitro inhibition and hydrolysis of a series of carba-
  Ikoxy homologs of malathion.  Toxicol. Appl. Pharmacol. 9:408-418.
Davis, H. C. and H. Hidu; 1969.  Effects of pesticides on embryonic de-
  velopment of clams and oysters and on survival and growth of the
  larvae.  U.S., Fish, Wild!. Serv., Fish Bull. 67:393-404.
Dennis, E. B. and C. A. Edwards; 1963.  Phytotoxicity of insecticides
  and acaricides.  II. Flowers and ornamentals.  Plant Pathol. 12:27-
  36.
Dieter, M. P. and J. L. Ludke; 1975.  Studies on combined effects of
  org aiophosphates and heavy metals in birds.  I. Plasma and brain
  cholinesterase in coturnix quail fed methyl mercury and orally dosed
  with parathion.  Bull. Environ. Contam. Toxicol. 13:257-262.
Dorough, H. W. and N. M. Randolph; 1967.  Comparative residual nature
  of certain insecticides applied as low volume concentrate and water
  emulsion sprays.  Bull. Environ. Contam. Toxicol. 2:340-348.
Dunachie, J. F. and W. W. Fletcher; 1969.  An investigation of the tox-
  icity of insecticides to birds' eggs using the egg-injection techni-
  que.  Ann. Appl. Biol. 64:409-423.
Eckert, J. E.; 1948.  Present relation of agricultural chemicals to
  beekeeping industry.  Am. Bee J. 88:129-131, 143-144.
Eder, F.; 1963.  Uber die PhytotoxitMt von Insektiziden.  Phytopathol.
  Z. 47:129-174.
Edery, H. and G. Schatzberg-Porath; 1960.  Effects of organophosphorus
  insecticides on amphibians.  Arch, intern, pharmacodynamie 124:212-
  224.  (Chem. Abstr. 54:13473c, 1960).
Edwards, 0. A. and A. R. Thompson; 1973.  Pesticides and soil fauna.
  Residue Reviews 45:1-79.
                                   500
-------
Edwards, 0. A., A. R. Thompson and J. R. Lofty; 1969.  Changes in soil
  invertebrate populations caused by organophosphorus insecticides.
  Proc. Brit. Insectic. Fungic. Conf., 4th, 1:48-55. (Chetn. Abstr. 71:
  122851g, 1969).
Eichelberger, J. W. and J. J. Lichtenberg; 1971.  Persistence of pes-
  ticides in river water.  Environ. Sci. Technol. 5:541-544.
Eisler, R. ; 1970a.  Factors affecting pesticide-induced toxicity in
  an estuarine fish.  Tech. Paper Bur. Sport Fish, and Wildlife #45-
  46, #45; 20 pp.
Eisler, R.; 1970b.  Acute toxicities of organochlorine and organophos-
  phorus insecticides to estuarine fishes.  Tech. Pap. Bur. Sport Fish.
  Wildl. 45-46, #46, 12 pp.
El-Refai, A. and T. L. Hopkins; 1966.  Parathion absorption, translo-
  cation, and conversion to para-oxon in bean plants.  J. Agr. Food
  Chem. 14:588-592.
Engst, R., H. Seidler and M. Haertig; 1966a.  The behavior and the dis-
                                32
  tribution of methyl parathion-  P in carrots  (Daucus carota").  1. La-
  beling and persistence of methyl parathion.  Nahrung 10:413-418.
  (Chem. Abstr. 66:10004u, 1967).
Engst, R., H. Seidler and M. Haertig; 1966b.  The behavior and the dis-
                                32
  tribution of methyl-parathion-  P in the carrot (Daucus carota).  II.
                                                  32
  Distribution and hydrolysis of methyl parathion-  P.  Nahrung 10:419-
  425. (Chem. Abstr. 66:10005x, 1967).
Eto, M.; 1974.  Organophosphorus Pesticides:  Organic and Biological
  Chemistry.   CRC Press, Cleveland, Ohio.
Faerman, I. S., I. D. Volkova and E. S. Parfenova; 1969.  Hematologi-
  cal shifts in workers engaged in the production of organophosphorus
  toxic chemicals.  Ter. Arkh. 41:23-28. (Chem. Abstr. 72:70361d, 1970).
Faust, S. D.  and H. M. Gomaa; 1972.  Chemical hydrolysis of some orga-
  nic phosphorus and carbamate pesticides in aquatic environments.
  Environ. Lett. 3:171-201.
                                  501
-------
Fest, C. and K. J. Schmidt; 1973.  The Chemistry of Organophosphorus
  Pesticides.  Springer-Verlag, N.Y.
Fukami, J. and T. Shishido; 1963.  Selective toxicities of organic
  phosphorus insecticides.  I. Activation of parathion in mammals and
  insects.  II. Degradation of ethyl parathion, methyl parathion,
  methyl para-oxon, and sumithion.  III. An enzyme system included in
  the cleavage of methyl parathion to demethyl parathion in the super-
  natant of some types of homogenates.  Botyo-Kagaku 28:63-69 I; 69-
  76 II.; 77-81 III. (Chem. Abstr. 60:15077g, 1964).
Fukuto, T. R. and R. L. Metcalf; 1969.  Metabolism of insecticides in
  plants and animals.  Ann. N.Y. Acad. Sci. 160:97-111,
Gabliks, J.; 1967.  Insecticidal compounds.  Effects on replication of
  vaccinia and polio viruses in human Chang-strain lever cells.  Arch.
  Environ. Health 14:698-702.
Gabliks, J. and L. Friedman; 1965.  Responses of cell cultures to in-
  secticides.  I. Acute toxicity to human cells.  Proc., Soc. Exptl.
  Biol. Med. 120:163-168.
Gabovich, R. D. and I. L. Kurennoi; 1966.  Ozonization of water con-
  taining huraic compounds, phenols, and pesticides.  Vop. Kommunal.
  Gig. 6:11-19. (Chem. Abstr. 68:89806s, 1968).
Gaines, T. B.; 1969.  Acute toxicity of pesticides.  Toxicol. Appl.
  Pharmacol. 14:515-534.
Galley, D. J.; 1972.  Persistence of some organophosphorus insecti-
  cides in hen-house litter.  Pestic. Sci. 3:19-23.
Gar, K. A., N. A. Sazonova and Y. N. Fadeev; 1955.  Decomposition and
  elimination from the rabbit organism of diethyl 4-nitrophenyl thio-
  phosphate after internal administration.  Doklady Akad. Nauk. SSSR
  102:185-187. (Chem. Abstr. 49:12710e, 1955).
Garretson, A. L. and C. L. San Clemente; 1968,  Inhibition of nitri-
  fying chemolithotrophic bacteria by several insecticides.  J. Econ.
  Entomol. 61:285-288.
                                 502
-------
Gaufin, A. R., L. Jensen and T. Nelson; 1961.  Bioassays determine pes-
  ticide toxicity to aquatic invertebrates.  Water and Sewage Works
  108:355-359.
Gaufin, A. R., L. D. Jensen, A. V. Nebeker, T. Nelson and R. W. Teel;
  1965.  Toxicity of ten organic insecticides to various aquatic in-
  vertebrates.  Water Sewage Works 112(7):276-279.
Gershon, S. and F. H. Shaw; 1961.  Psychiatric sequele of chronic ex-
  posure to organophosphorus insecticides.  Lancet 1961-1:1371-1374.
Getzin, L. W. ; 1967.  Metabolism of diazinon and Zinophos in soil.  J.
  Econ. Entomol. 60:505-508.
Getzin, L. W. ; 1968.  Persistence of diazinon and Zinophos in soil:
  effects of autoclaving, temperature, moisture and acidity.  J. Econ.
  Entomol. 61:1560-1565.
Getzin, L. W. and I. Rosefield; 1966.  Persistence of diazinon and Zi-
  nophos in soils.  J. Econ. Entomol. 59:512-516.
Getzin, L. W. and I. Rosefield; 1968.  Organophosphorus degradation by
  heat-labile substances in soil.  J. Agr. Food Chem. 16:598-601.
Getzin, L. W. and I. Rosefield; 1971.  Partial purification and prop-
  erties of a soil enzyme that degrades the insecticide malathion.
  Biochim. Biophys.  Acta 235:442-453.
Getzin, L. W. and C. H. Shanks, Jr.; 1970.  Persistence, degradation,
  and bioactivity of phorate and its oxidative analog in soil.  J. Econ.
  Entomol. 63:52-58.
Gil, I., J. Morales, A. Martin, C. Ruano and F. Aragones; 1970.  Ef-
  fects of some pesticides on Azotobacter.  Microbiol. Espan. 23:271-
  277.  (Chem. Abstr. 75:34405z, 1971).
Goldsworthy, M. C. and A. C. Foster; 1950.  Effect of organic sprays
  on orchard soils.   Am. Fruit Grower 70:No. 2,22,52-53.
Gomaa,  H. M., I. H.  Suffet and S. D. Faust; 1969.  Kinetics of hydro-
  lysis of diazinon and diazoxon.  Residue Reviews 29:171-190.
Gota, S., I. Muta and R. Sato; 1960.  Chemical studies of organophos-
  phorus insecticides.  XIV. Decomposition products of tnethylparathion
                                   503
-------
  in dust formulation.  Botyu-Kagaku 25:111-115. (Chem. Abstr. 61:
  8833a, 1964).
Graetz, D. A., G. Chesters, T. C. Daniel, L. W. Newland and G. B. Lee;
  1970.  Parathion degradation in lake sediment.  J. Water Pollut.
  Contr. Fed. 2:R76-R94.
Graham-Bryce, I. J.; 1967.  Adsorption of disulfoton by soil.  J. Sci.
  Food Agr. 18:72-77.
Grant, D. L., C. R. Sherwood and K. A. McCully; 1969.  Degradation and
  anticarboxylesterase activity of disulfoton and phorate after cobalt-
  60 gamma-irradiation.  J. Assoc. Offic. Anal. Chem. 52:805-811.
Green, V. A.; 1970.  Trace Subst. Environ. Health-3; Proa. Univ. Mo.
  Annu. Conf.3 3rd.  1969:183-209.  Hemphill, D. D., ed.; Univ. of
  Missouri, Columbia, Mo.  Effects of pesticides on rat and chick
  embryo.  (Chem. Abstr. 73:130169e, 1970).
Greenberg, J. and Q. N. LaHam; 1969.  Malathion-induced teratisms in the
  developing chick.  Can. J. Zool. 47:539-542.
Greenberg, J. and Q. N. LaHam; 1970.  Reversal of malathion-induced
  teratisms and its biochemical implications in the developing chick.
  Can. J. Zool. 48:1047-1053.
Gregory, W. W., Jr., J. K. Reed and L. E. Priester; 1969.  Accumula-
  tion of parathion and DDT by some algae and protozoa.  J. Protozool.
  16:69-71.
Griffiths, D. C. and N. Walker; 1970.  Microbiological degradation of
  parathion.  Meded. Fac. Landbouwwetensch., Rijksuniv. Gent. 35:805-
  810. (Chem. Abstr. 75:139688x, 1971).
Grunwell, J. R. and R. H. Erickson; 1973.  Photolysis of parathion  \0,
  0-diethyl-Ci-(4-nitrophenyl)thiophosphate] .  New products.  J. Agr.
  Food Chem. 21:929-931.
Gunner, H. B. and B. M. Zuckerman; 1968.  Degradation of diazinon by
  synergistic microbial action.  Nature 217:1183-1184.
Gyrisco, G. G., L. B. Norton, G. W. Trimberger, R. F. Holland, P. J.
  McEnerney and A. A. Muka; 1959.  Effects of feeding low levels of
                                   504
-------
  insecticide residues on hay to dairy cattle on flavor and residues
  in milk.  J. Agr. Food Chem. 7:707-711.
Gysin, H. and A. Margot; 1958.  Chemistry and toxicological properties
  of OjO-diethyl 0-(2-isopropyl-4-methyl-6-pyrimidyl) phosphorothioate
  (Diazinon).  J. Agr. Food Chem. 6:900-903.
Halvorson, H., M. Ishaque, J. Solomon and 0. W. Grussendorf; 1971.
  Biodegradability test for insecticides.  Can. J. Microbiol. 17:585-
  591.
Haque, R. and V. H. Freed; 1975.  Environmental Dynamics of Pesticides,
  Plenum Press, N.Y.  and London.
Harris, C. I.; 1969a.  Movement of pesticides in soil.  J. Agr. Food
  Chem. 17:80-82.
Harris, C. R.; 1964a.  Influence of soil type and moisture on toxicity
  of insecticides in soil to insects.  Nature 202:724.
Harris, C. R.; 1964b.  Influence of soil moisture on the toxicity of
  insecticides in a mineral soil to insects.  J. Econ. Entomol. 57:
  946-950.
Harris, C. R.; 1966.   Influence of soil type on the activity of insec-
  ticides in soil.  J. Econ. Entomol. 59:1221-1225.
Harris, C. R.; 1967.   Further studies on the influence of soil moisture
  on the toxicity of insecticides in soil.  J. Econ. Entomol. 60:41-47.
Harris, C. R.; 1969b.  Persistence of biological activity of some in-
  secticides in soils.  J. Econ. Entomol. 62:1437-1441.
Harris, C. R. and J.  L. Hitchon; 1970.  Laboratory evaluation of can-
  didate materials on potential soil insecticides.  J. Econ. Entomol.
  63:2-7.
Harris, C. R. and J.  H. Mazurek; 1966.  Laboratory evaluation of can-
  didate materials as potential soil insecticides.  J. Econ. Entomol.
  59:1215-1221.
Hartenstein, R. C.; 1960.  The effects of DDT and malathion on forest
  soil microarthropods.  J. Econ. Entomol. 53:357-362.
                                 505
-------
Heath, R. G., J. W. Spann, E. F. Hill and J. F. Kreitzer; 1972.  Com-
  parative dietary toxicities of pesticides to birds.  U.S. Fish
  Wildl. Serv., Spec. Sci. Rep.: Wildl. 152, 57 pp.
Heinicke, D. R. and J. W. Foott; 1966.  The effect of several phos-
  phate insecticides on photosynthesis of Red Delicious apple leaves.
  Can. J. Plant Sci. 46:589-591.
Hendrick, R. D., T. R. Everett and H. R. Caffey; 1966.  Effects of
  some insecticides on the survival, reproduction, and growth of the
  Louisiana red crawfish.  J. Econ. Entomol. 59:188-192.
Heuer, B., B. Yaron and Y. Birk; 1974.  Guthion half-life in aqueous
  solutions and on glass surfaces.  Bull. Environ. Contam. Toxicol.
  11:532-537.
Hightower, B. G. and D. F. Martin; 1958.  Effects of certain climatic
  factors on the toxicities of several organic phosphorus insecticides.
  J. Econ. Entomol. 51:669-671.
Hirakoso, S.; 1968.  Residual effectiveness of insecticides.  VII. In-
  activation of some insecticides by bacteria in mosquito-breeding
  polluted water.  Jap. J. Exp. Med. 38:327-334. (Chem. Abstr. 71:69620k,
  1969).
Hirakoso, S.; 1969.  Inactivating effects of microorganisms on insecti-
  cidal activity of Dursban.  Jap. J. Exp. Med. 39:17-20. (Chem. Abstr.
  72:76030s, 1970).
Hirano, C. and T. Yashima; 1969.  Adsorption, translocation, and per-
  sistence of diazinon in rice plants.  Nippon Oyu Dobutsu Konchu
  Gakkai-Shi 13:174-184. (Chem. Abstr. 73:242873c, 1970).
Hollingworth, R. M., T. R. Fukuto and R. L. Metcalf; 1967a.  Selecti-
  vity of Sumithion compared with methyl parathion.  Influence of
  structure on anticholinesterase activity.  J. Agr. Food Chem. 15:
  235-241.
Hollingworth, R. M., R. L. Metcalf and T. R. Fukuto; 1967b.  The sel-
  ectivity of Sumithion compared with methyl parathion.  Metabolism in
  the white mouse.  J. Agr. Food Chem. 15:242-249.
                                   506
-------
Hopkins, A. R. and V. M. Kirk; 1957.  Effect of several insecticides on
  the English red worm.  J. Econ. Entomol. 50:699-700.
Hsieh, D. P. H.; 1973.  Inhibition of aflatoxin biosynthesis of di-
  chlorvos.  J. Agr. Food Chem. 21:468-470.
Hsieh, D. P. H., T. E. Archer, D. M. Munnecke and F. E. McGowan; 1972.
  Decontamination of noncombustible agricultural pesticide containers
  by removal of emulsifiable parathion.  Environ. Sci. Technol. 6:826-
  829.
Huang, C. C.; 1973.  Effect on growth but not on chromosomes of the
  mammalian cells after treatment with three organophosphorus insec-
  ticides.  Proc. Soc. Exp. Biol. Med. 142:36-40.
Hubbell, D. H., D. F. Rothwell, W. B. Wheeler, W. B. Tappan and F. M.
  Rhoads; 1973.  Microbiological effects and persistence of some pes-
  ticide combinations in soil.  J. Environ. Qual. 2:96-99.
Hulea, A. and G. Piticas; 1971.  In vitro tests on the fungicidal ef-
  fect of some organophosphorus compounds.  An. Inst. Cercet. Prot.
  Plant, Acad. Stiinte Agr. Silvicic 9:547-559. (Chem. Abstr. 80:
  117011x, 1974).
Ibrahim, F. B., J. M. Gilbert, R. T. Evans and J. C. Cavgnol; 1969.
  Study of decomposition of Di-syston (03(9-diethyl S- QZ-(ethythio)
  ethyl] phosphorodithioate) on fertilizers by infrared, gas-liquid
  chromatography, and thin-layer chromatography.  J. Agr. Food Chem.
  17:300-305.
Iverson, F., D. L. Grant and J. Lacroix; 1975.  Diazinon metabolism in
  the dog.  Bull. Environ. Contain. Toxicol. 13:611-618.
Ivie, G. W. and J. E. Casida; 1971.  Sensitized photodecomposition and
  photosensitizer activity of pesticide chemicals exposed to sunlight
  on silica gel chromatoplates.  J. Agr. Food Chem. 19:405-409.
Iwata, Y., W. E.  Westlake and F. A. Gunther; 1973.   Persistence of
  parathion in six California soils under laboratory conditions.  Arch.
  Environ. Contam. Toxicol. 1:84-96.
                                  507
-------
Iwata, Y., M. E. Duesch, W. E. Westlake and F. A. Gunther; 1975.  Be-
  havior of five organophosphorus pesticides in dust derived from sev-
  eral soil types.  Bull. Environ. Contain. Toxicol. 14:49-56.
Jirik, V., J. Pokorny and H. Culikova; 1971.  Degradation of organo-
  phosphate insecticide in surface water.  Cesk. Hyg. 16:177-182.
  (Chem. Abstr. 76:31182j, 1972).
Johansen, C. A.; 1961.  Toxicity of certain insecticides to honeybees
  in the laboratory.  J. Econ. Entomol. 54:1008-1009.
Johansen, C. A., M. D. Coffey and J. A. Quist; 1957.  Effect of insec-
  ticide treatments to alfalfa on honeybees including insecticidal
  residue and honey flavor analysis.  J. Econ. Entomol. 50:721-723.
Johnston, W. R., F. T. Ittihadieth, K. B. Craig and A. F. Pillsbury;
  1967.  Insecticides in drainage tile effluent.  Water Resour. Res.
  3:525-537.
Jones, K. H., D. M. Sanderson and D. M. Noakes; 1968.  Acute toxicity
  data for pesticides.  World Rev. Pest Contr. 7:135-143.
Kageyama, M. E., W. A. Rawlins and L. W. Getzin; 1972.  Loss of acti-
  vity of diazinon for onion maggot control in marl-containing muck
  soil.  J. Econ. Entomol. 65:873-874.
Kalkat, G. S., R. H. Davidson and C. L. Brass; 1961.  Effect of con-
  trolled temperatures and humidity on the residual life of certain
  insecticides.  J. Econ. Entomol. 54:1186-1190.
Kalow, W. and A. V. Marton; 1961.  Second generation toxicity of mala-
  thion in rats.  Nature 192:464-465.
Kansouh, A. S. H. and T. L. Hopkins; 1968.  Diazinon absorption, trans-
  location, and metabolism in bean plants.  J. Agr. Food Chem. 16:446-
  450.
Kasting, R. and J. C. Woodward; 1951.  Persistence and toxicity of
  parathion when added to the soil.  Sci. Agr. 31:133-138.
Katz, M. ; 1961.  Acute toxicity of some organic insecticides to three
  species of salmonids and to the threespine stickleback.  Trans. Am.
  Fisheries Soc. 90:264-268.
                                  508
-------
Kawamori, I., T. Saito and K. lyatomi; 1971a.  Fate of organophospho-
  rus insecticides in soils.  I. Retention of phosphorus-32 labeled
  disulfoton and dimethoate in three soils.  Bochu-Kagaku 36:7-12.
  (Chem. Abstr. 76:139419f, 1972).
Kawamori, I., T. Saito and K. lyatomi; 1971b.  Fate of organophospho-
  rus insecticides in soils.  II. Changes of the retention and the
  metabolism of phosphorus-32 labeled disulfoton and dimethoate in
  soils.  Bochu-Kagaku 36:12-17. (Chem. Abstr. 76:139419f, 1972).
Kayser, H., D. Luedemann and H. Neumann; 1962.  VerSnderungen an Ner-
  venzellen nach Insektizid vergiftung bei Fischen und Krebsen.  Z.
  Angew. Zool. 49:135-148.
Keith, J. 0. and M. S. Mulla; 1966.  Relative toxicity of five organo-
  phosphorus mosquito larvicides to mallard ducks.  J. Wildlife Mana-
  gement 30:553-563.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1969.  Chemi-
  cal and thermal methods for disposing of pesticides.  Residue Re-
  view 29:89-104.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1972.  Chemi-
  cal and thermal aspects of pesticide disposal.  J. Environ. Qual. 1:
  63-65.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1972b.  Analy-
  sis of decomposition products of pesticides.  J. Agr. Food Chem. 20:
  341-343.
Keplinger, M. L. and W. B. Deichmann; 1967.  Acute toxicity of combi-
  nations of pesticides.  Toxicol. Appl. Pharmacol. 10:586-595.
Kimbrough, R. D. and T. B. Gaines; 1968.  Effect of organophosphorus
  compounds and alkylating agents on the rat fetus.  Arch. Environ.
  Health 16:805-808.
King, P. H., H. H. Yeh, P. S. Warren and C. W. Randall; 1969.  Distri-
  bution of pesticides in surface waters.  J. Amer. Water Works Assoc.
  61:483-486.
Kliger, L. and B. Yaron; 1975.  Parathion recovery from soils after a
  short contact period.  Bull. Environ. Contam. Toxicol. 13:714.
                                 509
-------
Klimmer, 0. R. and W. Plaff; 1955.  Vergleichende Untersuchungen iiber
  die Toxicitat organischer Thiophosphorsaureester.  Arzneimittel-
  Forsch. 5:626-630.
Knaak, J. B., M. A. Stahmann and J. E. Casida; 1962.  Feroxidase and
  ethylenediaminetetraacetic acid-ferrous iron catalysed oxidation and
  hydrolysis of parathion.  J. Agr. Food Chem. 10:154-158.
Knutson, H., A. M. Kadoum, T. L. Hopkins and G. F. Swoyer; 1971.  In-
  secticide usage and residues in a newly developed Great Plains irri-
  gation district.  Pestic. Monit. J. 5:17-27.
Kobayashi, T. and S. Katsura; 1968.  Soil application of insecticides.
  IV. Effects of systemic organophosphates on the nitrification of
  soil and on the growth and yield of potato.  Nippon. Oyo Dobutsu
  Konchu Gakkai-Shi 12:53-63.
Koivistoinen, P.; 1962b.  Effect of sunlight on the disappearance of
  parathion residues.  Acta. Agr. Scand. 12:283-297. (Chem. Abstr.
  59:5685h, 1963).
Koivistoinen, P. and M. Meilainen; 1962a.  Paper-chromatographic
  studies on the effect of ultraviolet light on parathion and its der-
  ivatives.  Acta Agr. Scand. 12:267-276. (Chem. Abstr. 59:4492g, 1963).
Koivistoinen, P., A. Karinpaa and M. Kononen; 1964.  Disappearance
  rates of malathion residues as affected by previous treatments with
  para-oxon, parathion, and malathion.  J. Agr. Food Chem. 12:555-557.
Kono, S.; 1974.  Absorption of diazinon in spinach, strawberries and
  onions.  Kinki Chugoku Nogyo Kenkyu 48:64-66. (Chem. Abstr. 82:
  120056n, 1975).
Konrad, J. G., D. E. Armstrong and G. Chesters; 1967.  Soil degradation
  of diazinon, a phosphorothioate insecticide.  Agron. J. 59:591-594.
Konrad, J. G., G. Chesters and D. E. Armstrong; 1969.  Soil degradation
  of malathion, a phosphorodithioate insecticide.  Soil Sci. Soc. Amer.,
  Proc. 33:259-262.
Kortus, J., K. Durcek, A. Pleskova and J. Mayer; 1968.  Resorption and
                        32
  organ distribution of   P-labeled parath:
  418-422. (Chem. Abstr. 69:95377q, 1968).
                      32
organ distribution of   P-labeled parathion in rats.  Cesk. Hyg. 13:
                                  510
-------
Krishnan, K. S., N. G. S. Raghavan, C. P. Nair and M. L. Mammen; 1958.
  Comparative field trials on the residual effectiveness of DDT, mala-
  thion, and diazinon.  Indian J. Malariol. 12:43-48. (Chen. Abstr.
  53:1621d, 1959).
Kubistova, J.; 1959.  Parathion metabolism in female rat.  Arch, in-
  tern, pharmacodynamie 118:308-316.  (Chem. Abstr. 53:14310i, 1959).
Kuhr, R. J., A. C. Davis and J. B. Bourke; 1974.  Dissipation of Gu-
  thion, Sevin, Polyram, Phygon, and  Systox from apple orchard soil.
  Bull. Environ. Contain. Toxicol. 11:224-230.
Lauro, V., C. Giornelli, A. Fanelli and M. Marinell; 1969.  Effects of
  anticholinesterases on implantation of fertile ova.  Comparison be-
  txveen rodent species.  Arch. Ostet. Ginecol. 74:368-380. (Chem.
  Abstr. 73:54957t, 1970).
Laygo, E. R. and J. T. Schulz; 1963.  Persistence of organophosphate
  insecticides and their effects on microfauna in soils.  Proc. N.
  Dakota Acad. Sci. 17:64-65. (Chem. Abstr. 60:7383e, 1964).
Lee, E. L. and J. C. Buzzell; 1969.  Measurement of pesticide toxici-
  ty by fish respiration.  Eng. Bull. Purdue Univ., Eng. Ext. Ser.
  #135, pt. 1, pp. 595-609.
Leenheer, J. R. and J. L. Ahlrichs; 1971.  Kinetic and equilibrium
  study of the adsorption of carbaryl and parathion upon soil organic
  matter surfaces.  Soil Soc. Amer., Proc. 35:700-705.
Leibovich, D. L.; 1973.  Embryotropic action of small doses of the or-
  ganophosphorus pesticides chlorophos, metaphos, and carbophos.  Gig.
  Sanit. 8:21-24. (Chem. Abstr. 80:5952, 1974).
Lenon, H., L. Curry, A. Miller and D. Patulski; 1972.  Insecticide
  residues in water and sediment from cisterns on the U.S. and British
  Virgin Islands. 1970.  Pestic. Monit. J. 6:188-193.
Lewis, D. L., D. F. Paris and G. L. Baughman; 1975.  Transfer of rnala-
  thion by a fungus, Aspergillus oryzae, isolated from a fresh water
  pond.  Bull. Environ. Contain. Toxicol. 13:596-601.
                                 511
-------
Liang, T. T. and E. P. Lichtenstein; 1972.  Effect of light, tempera-
  ture, and pH on the degradation of azinphosmethyl.  Econ. Entomol.
  65:315-321.
Liang, T. T. and E. P. Lichtenstein; 1974.  Synergism of insecticides
  by herbicides.  Effect of environmental factors.  Science 186:1128-
  1130.
Lichtenstein, E. P.; 1965.  Persistence and behavior of pesticidal res-
  idues in soils.  Their translocation into crops.  Arch. Environ.
  Health 10:825-827.
Lichtenstein, E. P.; 1966.  Increase of persistence and toxicity of
  parathion and diazinon in soils with detergents.  J. Econ. Entomol.
  59:985-993.
Lichtenstein, E. P. and K. R. Schulz; 1964.  The effect of moisture and
  microorganisms on the persistence and metabolism of some organophos-
  phorus insecticides in soils, with special emphasis on parathion.  J.
  Econ. Entomol. 57:618-627.
Lichtenstein, E. P. and K. R. Schulz; 1970.  Volatilization of insec-
  ticides from various substrates.  J. Agr. Food Chem. 18:814-818.
Lichtenstein, E. P., T. W. Fuhremann and K. R. Schulz; 1968.  Effect
  of sterilizing agents on persistence of parathion and diazinon in
  soils and water.  J. Agr. Food Chem. 16:870-873.
Lichtenstein, E. P., T. W. Fuhreman, K. R. Schulz and R. F. Skrentny;
  1967.  Effect of detergents and inorganic salts in water on the per-
  sistence and movement of insecticides in soils.  J. Econ. Entomol.
  60:1714-1721.
Lichtenstein, E. P., T. Fuhremann and K. R. Schulz; 1974.  Transloca-
  tion and metabolism of carbon-14-labeled phorate as affected by per-
  colating water in a model soil-plant ecosystem.  J. Agr. Food
  Chem. 22:991-996.
Lichtenstein, E. P., T. Fuhremann, K. R. Schulz and T. T. Liang; 1973.
  Effects of field application methods on the persistence and metabo-
  lism of phorate in soils and its translocation into crops.  J. Econ.
                                  512
-------
  Entomol. 66:863-866.
Lichtenstein, E. P., W. F. Millington and G. T. Cowley; 1962.  Effect
  of various insecticides on growth and respiration of plants.  J.
  Agr. Food Chem. 10:251-256.
Lilly, J. H., S. Moyhiyuddin, H. P. Prabhuswamy, J. C. Samuel and S. V.
  R. Shetty; 1969.  Effects of insecticide-treated rice plants and
  paddy water on vertebrate animals.  Mysore J. Agr. Sci. 3:371-379.
Lippold, P. C., J. S. Cleere, L. M. Massey, Jr., J. B. Bourke and A. W.
  Avens; 1969.  Degradation of insecticides by cobalt-60 <7aOT7za-radia-
  tion.  J. Econ. Entomol. 62:1509-1510.
Litterst, C. L. and E. P. Lichtenstein; 1971.  Effects and interactions
  of environmental chemicals on human cells in tissue culture.  Arch.
  Environ. Health 22:454-459.
Lord, K. A., M. A. May and J. H. Stevenson; 1968.  The secretion of
  the systematic insecticides dimethoate and phorate into nectar.  Ann.
  Appl. Biol. 61:19-27.
Luczak, J. and J. Maleszevska; 1966.  Effect of methyl parathion on
  physicochemical properties and bacterial growth in water.  Raczniki
  Panstwowego Zaklada Hig. 17:309-316. (Chem. Abstr. 65:20776d, 1966).
Luczak, J., J. Maleszewska, J. Stanislawska and D. Zycinski; 1973.
  Effect of organophosphorus pesticides (malathion, Foschlor, dichlor-
  vos) on the physicochemical properties of water and on aquatic orga-
  nisms.  Roca. Panstw. Zakl. Hig. 24:137-150. (Chem. Abstr. 80:6760w,
  1974).
Luedemann, D. and H. Neumann; 1961.  Versuche liber die akute toxische
  Wirkung neuzeitlicher Kontaktinsektizide auf Siisswassertiere. Zeit-
  schrift fur Angewandte Zoologie 48:87-96.
Luedemann, D. and H. Neumann; 1962.  Uber die Wirkung der neuzeitlichen
  Kontaktinsektiziden auf die Tiere des Stlsswassers. Anz. Schadlings-
  kunde 35:5-9.
Lutz-Ostertag, Y., R. Meiniel and H. Lutz; 1970.  Parathion and embryo
  development, sterilization, and feminization of birds.   Comparison
                                  513
-------
  with the effects of aldrin.  Annee. Biol. 9:501-507. (Chem. Abstr.
  74:22137e, 1971).
Lyon, W. F. and R. H. Davidson; 1965.  The effect of humidity on the
  volatilization of certain insecticides.  J. Econ. Entomol. 58:1037.
Macek, K. J., C. Hutchinson and 0. B. Cope; 1969.  Effects of tempera-
  ture on the susceptibility of bluegills and rainbow trout to selec-
  ted pesticides.  Bull. Environ. Contain. Toxicol. 4:174-183.
Machin, A. F., M. P. Quick, H. Rogers and N. F. Janes; 1972.  Isomer
  of hydroxydiazinon formed by metabolism in sheep.  Bull. Environ.
  Contain. Toxicol. 7:270-272.
Mackiewicz, M., K. H. Deubert, G. B. Haim and B. M. Zuckerman; 1969.
  Study of parathion biodegradation using gnotobiotic techniques.  J.
  Agr. Food Chem. 17:129-130.
MacNamara, G. M. and S. J. Toth; 1970.  Adsorption of linuron and mal-
  athion by soils and clay minerals.  Soil Sci. 109:234-240.
MacPhee, A. W. and K. H. Sanford; 1956.  Influence of spray programs
  on the fauna of apple orchards in Nova Scotia.  X. Effects on some
  beneficial anthropods.  Can. Entomol. 88:631-634.
Mahmoud, S. A. Z., S. M. Taha, A. M. Abdel-Hafez and A. S. Hamed; 1972,
  Effect of some pesticides on rhizosphere microflora of cotton plants,
  I. Insecticides and fungicides.  Egypt. J. Microbiol. 7:39-52.
Malone, C. R. and B. G. Blaylock; 1970.  Toxicity of insecticide for-
  mulations to carp embryos reared in vitro.  J. Wildl. Manage. 34:
  460-463.
Malone, C. R. and D. E. Reichle; 1973.  Chemical manipulation of soil
  biota in a fescue meadow.  Soil Biol. Biochem. 5:629-639.
Malone, C. R., A. G. Winnett and K. Helrich; 1967.  Insecticide-in-
  duced responses in an old field ecosystem:  persistence of diazinon
  in the soil.  Bull. Environ. Contain. Toxicol. 2:83-89.
March, R. B., R. L. Metcalf, T. R. Fukuto and F. A. Gunther; 1956.
  Fate of phosphorus-32-labeled malathion sprayed on Jersey heifer
  calves.  J. Econ. Entomol. 49:679-682.
                                  514
-------
Martin, H.; 1968.  Pesticide Manual.  British Crop Protection Council.
Masuda, T. and H. Fukada; 1970.  Behavior on and in rice plants of di-
  azinon applied onto the surface of paddy soil.  Bochu-Kagaku 35:134-
  140. (Chem. Abstr. 75:l09118u, 1971).
Masuda, T. and J. Kanazawa; 1972.  Residues of organophosphorus insec-
  ticides in crops treated with granular formulations.  Noyaku Seisan
  Gijutsu 29:29-35. (Chem. Abstr. 79:3937c, 1973).
Matsumura, F. and G. M. Boush; 1966.  Malathion degradation by Trioho-
  derma vivide and a Pseudomonas species.  Science 153:1278-1280.
Matsumura, F. and G. M. Boush; 1968.  Degradation of insecticides by a
  soil fungus, Triehoderma viride,   J. Econ. Entomol. 61:610-612.
McCarty, P. L. and P. H. King; 1966.  The movement of pesticides in
  soils.  Purdue Univ., Eng. Bull., Ext. Ser. #121, 156-171. (Chem.
  Abstr. 67:89422x, 1967).
Mclaughlin, J., Jr., J. P. Marliac, M. J. Verrett, M. K. Mutchler and
  0. G. Fitzhugh; 1963.  The injection of chemicals into the yolk sac
  of fertile eggs prior to incubation as a toxicity test.  Toxicol.
  Appl. Pharmacol. 5:760-771.
Meiniel, R.; 1973.  Axial skeleton malformations in chick and quail
  embryos developed from eggs treated with parathion during different
  stages of incubation.  C.R. Soc.  Biol. 167:459-462. (Chem. Abstr.
  80:10980k, 1974).
Meiniel, R.; 1974.  Action protectrice de la pralidoxime vis-a-vis des
  effets teratogenes du parathion sur la squelette axial de 1'embryon
  de Caille.  C.R. Hebd. Seances Acad. Sci., Ser. 0279:603-606.
Meiniel, R., Y. Lutz-Ostertag and H. Lutz; 1970.  Teratogenic effects
  of a commercial organophosphorus insecticide, parathion, on the em-
  bryonic skeleton of the Japanese quail.  Arch. Anat. Microsc. Mor-
  phol. Exp. 59:167-183. (Chem. Abstr. 76:21709x, 1972).
Meisch, H. V., G. L. Teetes, N. M.  Randolph and A. Bockholt; 1970.
  Phytotoxic effects of insecticides on six varieties of grain sorghum.
  J. Econ. Entomol. 63:1516-1517.
                                  515
-------
Mello, D., F. R. Puga and R. Benintendi; 1972.  Intoxication caused by
  products resulting from diazinon degradation, and their use as a
  tickicide.  Biologico 38:136-139. (Chem. Abstr. 78:12400d, 1973).
Mel'nikov, N. N., Y. A. Mandel'baum, E. I. Suentsitskii and Z. M. Baka-
  nova; 1958.  Detoxification of waste water from the production of
  parathion.  Nauchn. Inst. po. Udobr. i Insektofung. No. 158:60-64.
  (Chem. Abstr. 57:3221c, 1962).
Menzer, R. E. and L. P. Dittman; 1968.  Residues in spinach grown in di-
  sulfoton- and phorate-treated soil.  J. Econ. Entomol. 61:225-229.
Menzer, R. E., E. L. Fontanilla and L. P. Dittman; 1970.  Degradation
  of disulfoton and phorate in soil influenced by environmental factors
  and soil types.  Bull. Environ. Contam. Toxicol. 5:1-5.
Menzie, C. M.; 1972.  in:  Environmental Toxicology of Pesticides; pp.
  487-500.; F. Matsumura, G. Boush, T. Misato, eds.; Academic Press,
  N.Y.; Effects of pesticides on fish and wildlife.
Metcalf, R. L., T. R. Fukuto and R. B. March; 1957.  Plant metabolism
  of dithio-systox and thiraet.  J. Econ. Entomol. 50:338-345.
Metcalf, R. L., G. K. Sangha and I. P. Kapoor; 1971.  Model ecosystem
  for the evaluation of pesticide biodegradability and ecological mag-
  nification.  Environ. Sci. Technol. 5:709-713.
Metcalf, R. L. and J. R. Sanborn; 1975.  Pesticides and environmental
  quality in Illinois.  111. Nat. His. Survey Bull.
Meyers, N. L., J. L. Ahlrichs and J. L. White; 1970.  Adsorption of in-
  secticides on pond sediments and watershed soils.  Proc. Indiana
  Acad. Sci. 79:432-437. (Chem. Abstr. 73:119654p, 1970).
Milby; T. H. and W. L. Epstein; 1964.  Allergic sensitivity to mala-
  thion.  Arch. Environ. Health 9:434-437.
Miles, J. R. W., G. F. Manson, W. W. Sans and H. D. Niemczyk; 1967.
  Translocation of diazinon from planting water by cabbage and tobacco
  seedlings.  Can. J. Plant Sci. 47:187-192.
Milhaud, G., A. Bechade, L. Pinault, E. Charles, M. Sabbag and M. Graig-
  nic; 1971.  Contamination of milk by residues of ronnel and malathion
                                  516
-------
  used for disinfecting stables.  Reel. Med. Vet. 147:1053-1061.  (Chem.
  Abstr. 76:139169z, 1972).
Miller, C. W., B. M. Zuckerman and A. J. Charig; 1966.  Water translo-
                     14                35
  cation of diazinon-  C and parathion-  S off a model cranberry bog
  and subsequent occurrence in fish and mussels.  Trans. Amer. Fish
  Soc. 95:345-349.
Minchew, C. W. and D. E. Ferguson; 1969.  Toxicities of insecticides
  to resistant and susceptible green sunfish and golden shiners in
  static bioassays.  J. Miss. Acad. Sci. 15:29-32.  (Chem. Abstr. 73:
  86892J, 1970).
Mistric, W. J. and J. C. Gaines; 1953.  Effect of wind and other fac-
  tors on the toxicity of certain insecticides.  J. Econ. Entomol. 46:
  341-349.
Mistric, W. J., Jr. and D. F. Martin; 1956.  Effect of sunlight and
  other factors on the toxicity of insecticides.  J. Econ. Entomol. 49:
  757-760.
Mohn, G.; 1973.  5-methyltryptophan resistance mutations in Esaheviohia
  ooli, K-12.  Mutagenic activity of monofunctional alkylating agents
  including organophosphorus insecticides.  Mutat. Res. 20:7-15.
Mol, J. C. M., D. L. Harrison and R. H. Telfer; 1972.  Parathion.  Tox-
  icity to sheep and persistence on pasture and in soil.  N.Z. J. Agr.
  Res. 15:306-320.
Moore, R. B.; 1970.  Effects of pesticides on growth and survival of
  Euglena graoilis Z.  Bull. Environ. Contam. Toxicol. 5:226-230.
Mosher, D. R. and A. M. Kadoum; 1972.  Effects of four lights on mala-
  thion residues on glass beads, sorghum grain, and wheat grain.  J.
  Econ. Entomol. 65:847-850.
Mostafa, I., I. M. I. Fakhr, M. R. E. Bahig and Y. A. El-Zawahry; 1972.
  Metabolism of organophosphorus insecticides.  XIII. Degradation of
  malathion by Rhizobium species.  Arch. Mikrobiol. 86:221-224.
Mostafa, I. Y., M. R. E. Bahig, I. M. I. Fakhr and Y. Adam; 1972b.
  Metabolism of organophosphorus insecticides.  XIV. Malathion break-
  down by soil fungi.  Z. Naturforsch. B. 27:1115-1116.
                                  517
-------
Motoyama, N.; 1972.  In vitro metabolism of azinphosmethyl by mouse
  liver.  Pestic. Biochem. Physiol. 2:170-177.
Mount, D. I. and H. W. Boyle; 1969.  Parathion-use of blood concentra-
  tion to diagnose mortality of fish.  Environ. Sci. Technol. 3:1183-
  1185.
Muecke, W., K. 0. Alt and H. 0. Esser; 1970.  Degradation of carbon-14
  labeled diazinon in the rat.  J. Agr. Food Chem. 18:208-212.
Mulla, M. S.; 1962.  Frog and toad control with insecticides.  Pest.
  Control 30:No. 10, 20, 64.
Mulla, M. S.; 1963.  Persistence of mosquito larvicides in water.  Mos-
  quito News 23:234-237.
Mulla, M. S. and L. W. Isaak; 1961.  Field studies on the toxicity of
  insecticides to the mosquito fish, Gambusia affinis.  J. Econ. Ento-
  mol. 54:1237.
Mulla, M. S., L. W. Isaak and H. Axelrod; 1963.  Field studies on the
  effects of insecticides on some aquatic wildlife species.  J. Econ.
  Entomol. 56:184-188.
Munnecke, D. M. and D. P. H. Hsieh; 1975.  Microbial metabolism of a
  parathion-xylene pesticide formulation.  Appl. Microbiol. 30:575-
  580.
Murphy, S. D., R. R. Lauwerys and K. L. Cheever; 1968.  Comparative an-
  ticholinesterase action of organophosphorus insecticides in vertebrates.
  Toxicol. Appl. Pharmacol. 12:22-35.
Naishtein, S. Y., V. A. Zhulinskaya and E. M. Yurovskaya; 1973.  Sta-
  bility of certain organophosphorus pesticides in the soil.  Gig.
  Sanit. 7:42-45.  (Chem. Abstr. 80:34361k, 1974).
Nakatsugawa, T. and P. A. Dahm; 1967.  Microsomal metabolism of para-
  thion.  Biochem. Pharmacol. 16:25-38.
Naqvi, S. M. and D. E. Ferguson; 1968.  Pesticide tolerances of selec-
  ted freshwater invertebrates.  J. Miss. Acad. Sci. 14:121-127. (Chem.
  Abstr. 72:65811w, 1970).
                                   518
-------
Nash, R. G.; 1967.  Phytotoxic pesticide interactions in soil.  Agron.
  J. 59:227-230.
Nasim, A. I., M. M. H. Baig and K. A. Lord; 1972.  Loss of diazinon
  from Dacca paddy field soil.  Pak. J. Sci. Ind. Res. 15:330-332.
  (Chem. Abstr. 79:74887x, 1973).
Naumann, K.; 1959.  Effect of pesticides on the soil microflora.  Mitt.
  Biol. Bundesanstalt Land-Forstwirtch, Berlin-Dahlem 97:109-117.
  (Chem. Abstr. 57:8962h, 1962).
Naumann, K.; 1958.  The influence on the microflora in soils of para-
  thion.  Naturwissenschaften 45:395-396.  (Chem. Abstr. 53:3580a, 1959).
Naumann, K.; 1967.  Uber den Parathionabbau durch Bodenbakterien.  Phy-
  topathol. Z. 60:343-357.
Naumann, K.; 1970a.  Zur Dynamik der Bodenmikroflora nach Anwendung
  von Pflanzenschutzmitteln.  Phytopathol. Z. 68:9-34.
Naumann, K.; 1970b.  Zur Dynamik der Bodenmikroflora nach Anwendung
  von Pflanzenschutzmitteln.  Zentralbl. Bakteriol., Parasitenk., In-
  fektionskr. Hyg., Abt. 2, 124:743-754.
Naumann, K.; 1970c.  Zur Dynamik der Bodenmikroflora nach Anwendung
  von Pflanzenschutzmitteln.  II. Die Reaktion verschiedener physiolo-
  gischer Gruppen von Bodenbakterien auf den Einsatz von Parathion-
  methyl im Freiland.  Zentralbl. Bakteriol., Parasitenk., Infektion-
  skr. Hyg., Abt. 2, 124:755-765.
Naumann, K.; 1970d.  Zur Dynamik der Bodenmikroflora nach Anwendung
  von Pflanzenschutzmitteln.  IV. Untersuchungen iiber die Wirkung von
  Parathion-methyl auf die Atmung und die Dehydrogenase-Aktivitat des
  Bodens.  Zentralbl. Bakteriol., Parasitenk., Infektionskr., Hyg.,
  Abt. 2, 125:119-133.
Naumann, K.; 1971.  VerSnderung in der Zusammensetzung der Bodenbakter-
  ienflora nach Einbringung von Pflanzenschutzmitteln in den Boden.
  Zentralbl. Bakteriol., Parasitenk., Infektionskr. Hyg., Abt. 2, 126:
  530-544.
                                  519
-------
Neal, R. A.; 1967.  Studies on the metabolism of diethyl 4-nitrophenyl
  phosphorothionate (parathion) in vitro.  Biochem. J. 103:183-191.
Nelson, D. L. ; 1974.  Pharmacology and toxicology of Guthion.  Residue
  Reviews 51:136-139.
Nestor, I.; 1972.  Influence of organophosphorus insecticides of the
  malathion and bromofos type on gram-positive bacteria.  Igiena 20:
  723-730. (Chem. Abstr. 77:148288k, 1972).
Nicholson, H. P., H. J. Webb, G. J. Lauer, R. E. O'Brien, A. R. Grzenda
  and D. W. Shanklin;  1962.  Insecticide contamination in a farm pond.
  I. Origin and duration.  II. Biological Effects.  Trans. Am. Fisher-
  ies Soc. 91:213-217, 217-222.
Noda, K., H. Numata, M. Hirabayashi and I. Endo; 1972.  Effects of pes-
  ticides on embryos.    I. Effects of organophosphorus pesticides.  Oyo
  Yakuri 6:667-672. (Chem. Abstr. 78:53685u, 1973).
O'Brien, R. D.; 1957.   Properties and metabolism in the cockroach and
  mouse of malathion and malaoxon.  J. Econ. Entomol. 50:159-164.
O'Brien, R. D., W. C.  Dauterman and R. P. Niedermeier; 1961.  The meta-
  bolism of orally administered malathion by a lactating cow.  J. Agr.
  Food Chem. 9:39-42.
Obuchowska, I.; 1967.   Stability of organophosphorus pesticides (methyl
  parathion) in soils.  Rocz. Panstw. Zakl. Hig. 18:655-659. (Chem.
  Abstr. 68:94829f, 1968).
Oehler, D. D., J. L. Eschle, J. A. Miller, H. V. Claborn and M. C. Ivey;
  1969.  Residues in milk resulting from ultra-low volume sprays of
  malathion, methoxychlor, coumaphos, ronnel, or Gardona for control of
  the horn fly.  J. Econ. Entomol. 62:1481-1483.
Ostojic, N., N. Starovic and M. Zigic; 1972.  Mobility of some organo-
  phosphorus insecticides and lindane in different soil types.  Zast.
  Bilja 23:285-291.
Palut, D. and T. Syrowatka; 1968.  Metabolism of organophosphorus in-
  secticides in suspensions of Chlorella vulgaris cells.  Panstw. Zakl.
  Hig. 19:669-674.  (Chem. Abstr. 71:2506j, 1969).
                                   520
-------
Pankaskie, J. E., F. C. Fountaine and P. A. Dahm; 1952.  Degradation
  and detoxification of parathion in dairy cows.  J. Econ. Entomol.
  45:51-60.
Parakova, E. and V. Kremery; 1967.  Effects of insecticides and their
  combinations on the growth of Euglena grac-il-is.  Cesk. Hyg. 12:473-
  476.
Paris, D. F. and D. L. Lewis; 1973.  Chemical and microbial degrada-
  tion of ten selected pesticides in aquatic systems.  Residue Reviews
  45:95-124.
Paris, D. F., D. L. Lewis and N. L. Wolfe; 1975.  Rates of degradation
  of malathion by bacteria isolated from aquatic culture.  Environ.
  Sci. Technol. 135-138.
Parker, B. L. and J. E. Dewey; 1965.  Decline of phorate and dimethoate
  residues in treated soils based on toxicity to Drosophila melanogas-
  ter.  J. Econ. Entomol. 58:106-111.
Payton, J.; 1953.  Parathion and ultraviolet light.  Nature 171:355-356.
Pechon, J., J. Lajudie and 0. Coppier; 1951.  Remarques sur les recher-
  ches relatives a 1'action de certaines substances antiparasitaires
  sur la microflores du sol.  Ann. Inst. Pasteru 80:517-519.
Pickering, Q. H., C. Henderson and A. E. Lemke; 1962.  The toxicity of
  organic phosphorus insecticides to different species of warm-water
  fishes.  Trans. Am. Fisheries Soc. 91:175-184.
Pimentel, D.; 1971.  Ecological Effects of Pesticides on Non-Target
  Species.  U.S. Gov't Printing Office #4106-0029.
Plapp, F. W. and J. E. Casida; 1958.  Hydrolysis of the alkyl phosphate
  bond in certain dialkyl aryl phosphorothioate insecticides by rats,
  cockroaches and alkali.  J. Econ. Entomol. 51:800-803.
Polizu, A. and S. Floru; 1967.  Investigation of certain factors which
  determine loss of DDT and parathion.  An. Inst. Cercet. Prot. Plant,
  Acad. Stiinte Agr. Silvice 5:467-472. (Chem. Abstr. 73:54955r, 1970).
Popov, P. V.; 1958.  The toxicity for infusoria of some organic phos-
  phorus compounds.  Org. Insektofungitsidy i Gerbitsidy 1958, 128-130.
  (Chem. Abstr. 54:14487c, 1960).
                                  521
-------
Popov, P. V. and Y. S. Khol'kin; 1958.  Decomposition of (EtO)_ (p-
  0~NCfiH,0)PS after spraying and dusting.  Org. Insektofungitsidy i
  Gerbitsidy 1958, 64-68. (Chem. Abstr. 54:7052g, 1960).
Quinby, G. E.,  K. C. Walker and W. F. Durham; 1958.  Public health haz-
  ards involved in the use of organic phosphorus insecticides in cotton
  culture in the delta area of Mississippi.  J. Econ. Entomol. 51:831-
  838.
Rajaram, K. P.  and N. Sethunathan; 1975.  Effect of organic sources on
  the degradation of parathion in flooded alluvial soil,  Soil Science
  119:296-300.
Raman, R. and K. K. Krishnamoorthy; 1973.  Decomposition of the active
  ingredients of pesticides during storage.  Pesticides 7:20.
Ramaraje-Urs, N. V., H. C. Govindu and K. S. Shivashankara-Shastry;
  1967.  The effect of certain insecticides on the entomogenous fungi,
  Beauveria bassiana and Metarrhisium ani-sopliae.  J. Invertebr. Pathol.
  9:398-403.
Ramu, A. and H. Drexler; 1973.  Hyperglycemia in acute malathion into-
  xification in rats.  Isr. J. Med. Sci. 9:635-639.  (Chem. Abstr. 79:
  74580s, 1973).
Randall, C. W., M. Asce and R. A. Lauderdale; 1967.  Biodegradation of
  malathion.  J. Sanit. Eng. Div. Proc. Amer. Soc. Civil Eng. 93:145-
  156.
Ranke-Rybicka,  B. and J. Stanislawska; 1972.  Changes in periphyton or-
  ganisms caused by organophosphorus pesticides (malathion, phoschlor).
  Rocz. Panstw. Zakl. Hig. 23:137-146.
Rao, A. V. and N. Sethunathan; 1974.  Degradation of parathion by Peni-
  o'Llliian wdksmani. isolated from flooded acid sulfate soil.  Arch.
  Microbiol. 97:203-208.
Ravindran, P. N.; 1971.  Cytological effects of folidol.  Cytologia 36:
  504-514.
Read, D. C.; 1969.  Persistence of some newer insecticides in mineral
  soils measured by bioassay.  J. Econ. Entomol. 62:1338-1342.
                                  522
-------
Reis, C. C. A., I. Pellegatti, S. Oga and A. C. Zanini; 1971.  Toxic
  and teratogenic activities of anticholinesterase substances.  I.
  Teratogenic activity of parathion in chick embryos.  Rev. Farm
  Bioquim. Univ. Sao Paulo 9:343-355. (Chem. Abstr. 77:135969h, 1972).
Richert, E. P. and K. V. Prahlad; 1972.  Effect of the organophosphate
  0,0 diethyl S- |£ e thy Ithio) methyl]  phosphorodithioate on the chick.
  Poult. Sci. 51:613-619.
Rider, J. A., H. C. Moeller, E. J. Puletti and J. I. Swader; 1969.
  Toxicity of parathion, syston, octamethylpyrophosphoramide, and
  methyl parathion.  Toxicol. Appl. Pharmacol. 14:603-611.
Ritter, W. F., H. P. Johnson and W. G. Lovely; 1973.  Diffusion of at-
  razine, propachlor, and diazinon in a silt loam soil.  Weed Sci. 21:
  381-384.
Ritter, W. F., H. P. Johnson, W. G. Lovely and M. Molnau; 1974.  Atra-
  zine, propachlor, and diazinon residues on small agricultural water-
  sheds.  Runoff losses, persistence, and movement.  Environ. Sci.
  Technol. 8:38-42.
Robeck, G. G., K. A. Dostal, J. M. Cohen and J. F. Kreissl; 1965.  Ef-
  fectiveness of water treatment processes in pesticide removal.  J.
  Am. Water Works Assoc. 57:181-200.
Robens, J. F.; 1969.  Teratologic studies of carbaryl, diazinon, norea,
  disulfiram, and thiram in small laboratory animals.  Toxicol. Appl.
  Pharmacol. 15:152-163.
Roberts, J. E., R. D. Chisholm and L. Koblitsky; 1962.  Persistence of
  insecticides in soil and their effects on cotton in Georgia.  J.
  Econ. Entomol. 55:153-155.
Robson, H. and H. B. Gunner; 1970.  Differential response of soil micro-
  flora to diazinon.  Plant Soil 33:613-621.
Roger, J. C., D. G. Upshall and J. E. Casida; 1969.  Structure-activity
  and metabolism studies on organophosphate teratogens and their alle-
  viating agents in developing hen eggs with special emphasis on Bidrin.
  Biochem. Pharmacol. 18:373-392.
                                  523
-------
Rowlands, D. G.; 1966.  Activation and detoxification of three organic
  phosphorothioate insecticides applied to stored wheat grains.  J.
  Stored Prod. Res. 2:105-116.
Sacher, R. M., G. F. Ludvik and J. M. Deming; 1972.  Bioactivity and
  persistence of some parathion formulations in soil.  J. Econ. Ento-
  mol. 65:329-332.
Saini, M. L., H. Borough and H. Wyman; 1970.  Persistence of malathion
  and methyl parathion when applied as ultra-low-volume and emulsifi-
  able concentrate sprays.  J. Econ. Entomol. 63:405-408.
Salem, S. H., J. Szegi and F. Gulyas; 1971.  Influence of some insec-
  ticides on the symbiosis of rhizobia and legume plants.  Agrokem.
  Talajian 20:581-589. (Chem. Abstr. 77:84152b, 1972).
Saltzman, S. and B. Yaron; 1972.  in:  Pestie.  Chem. 3 Proa.  Int. Congr.
  Pestia. Chem., 2nd, 6:87-100.  Parathion adsorption from aqueous so-
  lutions as influenced by soil components.
Saltzman, S., L. Kliger and B. Yaron; 1972.  Adsorption-desorption of
  parathion as affected by soil organic matter.  J. Agr. Food Chem.
  20:1224-1226.
Sauter, E. A. and E. E. Steele; 1972.  Effect of low level pesticide
  feeding on the fertility and hatchability of chicken eggs.  Poultry
  Sci. 51:71-76.
Schafer, E. W.; 1972.  Acute oral toxicity of 369 pesticidal, pharma-
  ceutical, and other chemicals to wild birds.   Toxicol. Appl. Phar-
  macol. 21:315-330.
Scheffer, F., E. Welte and A. Kloke; 1952.  The effect of pesticides
  upon soils and plants.  Z. PflanzenernShr. Dungung. u Bodenk 56:
  151-171. (Chem. Abstr. 47:7147c, 1953).
Schulz, K. R., E. P. Lichtenstein, T. W. Fuhremann and T. T. Liang;
  1973.  Movement and metabolism of phorate under field conditions
  after granular band applications.  J. Econ. Entomol. 66:873-875.
Sethunathan, N.; 1972a.  Diazinon degradation in submerged soil and
  rice-paddy water.  Advan. Chem. Ser. 111:244-255.
                                 524
-------
Sethunathan, N.; 1972b.  Increased biological hydrolysis of diazinon
  after repeated application in rice paddies.  J. Agr. Food Chem. 20:
  586-589.
Sethunathan, N.; 1973a.  Microbial degradation of insecticides in
  flooded soil and in anaerobic cultures.  Residue Reviews 47:143-165.
Sethunathan, N.; 1973b.  Organic matter and parathion degradation in
  flooded soil.  Soil Biol. Biochem. 5:641-644.
Sethunathan, N.; 1973c.  Degradation of parathion in flooded acid soils.
  J. Agr. Food Chem. 21:602-604.
Sethunathan, N. and I. C. MacRae; 1969.  Persistence and biodegrada-
  tion of diazinon in submerged soils.  J. Agr. Food Chem. 17:221-225.
Sethunathan, N. and T. Yoshida; 1969.  Fate of diazinon in submerged
  soil.  Accumulation of hydrolysis product.  J. Agr. Food Chem. 17:
  1192-1195.
Sethunathan, N. and T. Yoshida; 1972.  Conversion of parathion to p-
  nitrophenol by a diazinon-degrading bacterium, Flavobaaterium species.
  Inst. Environ. Sci., Tech. Meet., Proc. 18:255-257.
Sethunathan, N. and T. Yoshida; 1973a.  Flavobacterium species that de-
  grades diazinon and parathion.  Can. J. Microbiol. 19:873-875.
Sethunathan, N. and T. Yoshida; 1973b.  Parathion degradation of sub-
  merged rice soils in the Philippines.  J. Agr. Food Chem. 21:504-506.
Sethunathan, N., S. Caballa and M. D. Pathak; 1971.  Absorption and
  translocation of diazinon by rice plants from submerged soils and
  paddy water and the persistence of residues in plant tissues.  J.
  Econ. Entomol. 64:571-576.
Sherman, M., R, B. Herrick, E. Ross and M. T. Y. Chang; 1967.  Further
  studies on the acute and subacute toxicity of insecticides to chicks.
  Toxicol. Appl. Phannacol. 11:49-67.
Shevchenko,  M. A., P. V. Marchenko and P. N. Taran; 1974.  Removal of
  agricultural pesticide residues from water.  Vodn. Resur.  (4):97-
  104. (Chem. Abstr. 83:54518g, 1975).
                                  525
-------
Siddaramappa, R.,  K. P. Rajaram and N. Sethunathan; 1973.  Degradation
  of parathion by bacteria isolated from flooded soil.  Appl. Micro-
  biol. 26:846-847.
Singh, G.;  1974.  Degradation of insecticides by the cultural symbiotes
  of Cletus signatus walker (Coreidae3 Heteroptera).  Curr. Sci. 43:
  624-625.
Singh, K. and K. C. Gulati; 1972.  Effects of di-syston and thimet on
  soil micro-organisms.  Ammonification and nitrification in soil.
  Pesticides 6:24-25.
Singh, K.,  K. C. Gulati and R. S. Dewan; 1972.  Persistence of disyston
  residues  in soil and plant.  Indian J. Agr. Sci. 42:1135-1138. (Chem.
  Abstr. 79:14421f, 1973).
Smith, F. F.; 1950.  Translocation of parathion from foliage applica-
  tions.  J. Econ. Entomol. 43:705-712.
Sommer, K.; 1970.   Effect of various pesticides on nitrification and
  nitrogen  transformation in soils.  Landwirt. Forsch., Sonderh. 25:
  22-30. (Chem. Abstr. 74:110863u, 1971).
Spear, R. C., W. J. Popendorf, J. T. Leffingwell and D. Jenkins; 1975.
  Parathion residues on citrus foliage, decay and decomposition as re-
  lated to  worker hazard.  J. Agr. Food Chem. 23:808-810.
Spiller, D.; 1961.  A digest of available information in the insecti-
  cide malathion.   Adv. Pest Control Research 4:249.
Sreenivasulu, S. and G. Rangaswami; 1973.  Effects of three granular
  organophosphorus insecticides on soil microflora.  Indian J. Micro-
  biol. 13:89-95.
Stadnyk, L., R. S. Campbell and B. T. Johnson; 1971.  Pesticide effect
  on growth and carbon-14 assimilation in a freshwater alga.  Bull.
  Environ.  Contain. Toxicol. 6:1-8.
Staiff, D.  C., S.  W. Comer, J. F. Armstrong and H. R. Wolfe; 1975.
  Persistence of azinphosmethyl in soil.  Bull. Environ. Contain. Toxi-
  col. 13:362-368.
                                  526
-------
Stanley, C. W., J. E. Barney II, M. R. Helton and A. R. Yobs; 1971.
  Measurement of atmospheric levels of pesticides.  Environ. Sci.
  Technol. 5:430-435.
Stathopoulos, D. G., L. Zenon-Roland, J. Biernaux and E. Seutin; 1971.
  Control of Psila rosae in 1969.  II. Organophosphorus insecticide
  levels in carrots and soil.  Meded. Fac. Landbouwwetensch. Rijksu-
  niv. Gent. 36:410-418.
Steelman, C. D., L. C. Colmer, H. T. Barr and B. A. Tower; 1967. Rela-
  tive toxicity of selected insecticides to bacterial populations in
  water disposal lagoons.  J. Econ. Entomol. 60:467-468.
Stewart, D. K. R., D. Chisholm, and M. T. H. Ragab; 1971.  Long term
  persistence of parathion in the soil.  Nature 229:47.
Steve, P. C., D. L. Anderson and J. H. Lilly; 1961.  Effects of die-
  tary Guthion on baby chicks.  J. Econ. Entomol. 54:1229.
Stitt, L. L. and J. Evanson; 1949.  Phytotoxicity and off-quality of
  vegetables grown in soil treated with insecticides.  J. Econ. Ento-
  mol. 42:614-617.
Stobwasser, I. H.; 1963.  Untersuchung der Riickstande einiger Phosphor-
  sSure-ester und von Sevin in Mb'hren nach Freilandbehandlung.  Z.
  PflanzenKrankh. Pflanzenschutz 70:459-464.
Stojanovic, B. J., M. V. Kennedy and F. L. Shuman, Jr.; 1972a.  Eda-
  phic aspects of the disposal of unused pesticides, pesticide wastes,
  and pesticide containers.  J. Environ. Qual. 1:54-62.
Stojanovic, B. J., F. Hutto, M. V. Kennedy and F. L. Shuman, Jr.; 1972b.
  Mild thermal degradation of pesticides.  J. Environ. Qual. 1:397-401.
Stutz, C. N.; 1966.  Treating parathion wastes.  Chem. Eng. Progr. 62:
  82-84.
Suett, D. L.; 1971.  Persistence and degradation of chlorfenvinphos,
  diazinon, fonofos, and phorate in soils and their uptake by carrots.
  Pestic. Sci. 2:105-112. (Chem. Abstr. 75:87439v, 1971).
Sunada, T.; 1967.  Use of radiation for treatment of polluted water.
  Genshirvoku Kogyo 13:34-37. (Chem. Abstr. 67:57087w, 1967).
                                   527
-------
Swoboda, A. R. and G. W. Thomas; 1968.  Movement of parathion in soil
  columns.  J. Agr. Food Chera. 16:923-927.
Tagatz, M. E., D. W. Borthwick, G. H. Cook and D. L. Coppage; 1974.
  Effects of ground applications of malathion on salt-marsh environ-
  ments in northwestern Florida.  Mosq. News 34:309-315.
Takase, I. and H. Nakamura; 1974.  Fate of ethylthiometon in paddy soil.
  Nippon Nogei Kagaku Kaishi 48:27-34. (Chem. Abstr. 81:131536z, 1974).
Takase, I., H. Tsuda and Y. Yoshimoto; 1971.  Fate of disulfoton in
  soil.  Nippon Oyo Dobutsu Knochu Gakkai-Shi 15:63-69. (Chem. Abstr.
  76:55246j, 1972).
Takase, I., H. Tsuda and Y. Yoshimoto; 1972.  Fate of disyston active
  ingredient in soil.  Pflanzenschutz-Nachr. (Amer. Ed.).  25:43-63.
  (Chem. Abstr. 80:67395c, 1974).
Takehara, H., M. Kotakemori and T. Oishi; 1967a.  The stability of or-
  ganophosphorus pesticides.  II. Relation of thermally accelerated
  degradation test to stability of organophosphorus pesticide dust for-
  mulation.  Nippon Nogei Kagaku Kaishi 41:203-208. (Chem. Abstr. 67:
  81418a, 1967).
Takehara, H., M. Kotakemori and T. Oishi; 1967b.  The stability of or-
  ganophosphorus pesticides.   IV. Effect of the physical and chemical
  properties of mineral diluents on the degradation of organophosphorus
  pesticide dust formulation.  Nippon Nogei Kagaku Kaishi 41:209-219.
  (Chem. Abstr. 67:8l419b, 1967).
Talens, G. and D. Woolley; 1973.  Effects of parathion administration
  during gestation in the rat on the development of the young.  Proc.
  West Pharmacol. Soc. 16:141-145.
Tanimura, T., K. Tamio and H. Nishimura; 1967.  Embryotoxicity of acute
  exposure to methyl parathion in rats and mice.  Arch. Environ. Health
  15:609-613.
Thompson, A. R.; 1973.  Persistence of biological activity of seven in-
  secticides in soil assayed with Folsomia Candida.  J. Econ. Entomol.
  66:855-857.
                                  528
-------
Tomizawa, C., T. Sato, H. Yamashita and H. Fukuda; 1962.  Decomposition
  products of organophosphorus insecticides in rice grains.  Shokuhin
  Eiseigaku Zasshi 3:72-76.
Toor, H. S., K. Mehta and S. Chhina; 1973.  Toxicity of insecticides
  (Commercial formulations) to the exotic fish, common carp, Cypm,nus
  aarp-io eommunis.   J. Res., Punjab Agr. Univ. 10:341-345.
Triolo, A. J. and J. M. Coon; 1966.  Toxicological interactions of
  chlorinated hydrocarbon and organophosphate insecticides.  J. Agr.
  Food Chem. 14:549-555.
Triolo, A. J., E. Mata and J. M. Coon; 1970.  Effects of organochlorine
  insecticides on the toxicity and in vitro plasma detoxication of para-
  oxon.  Toxicol. Appl. Pharmacol. 17:174-180.
Trojanowski, H. and Z. Zwolinska-Sniatalowa; 1967.  Solvirex residues
  in potato tubers.  Pr. Nauk. Inst. Ochr. Rosl. 9:257-261. (Chem.
  Abstr. 70:95529m, 1969).
Tsoneva-Maneva, M.  T., F. Kaloyanova and V. Georgieva; 1969.  Mutagenic
  effect of diazinon on human peripheral blood lymphocytes in vitro.
  Eksp. Med. Morfol. 8:132-136.
Tu, C-M.; 1970.  Effect of four organophosphorus insecticides in micro-
  bial activities in soil.  Appl. Microbiol. 19:479-484.
Tucker, R. K. and D. G. Crabtree; 1970.  Handbook of toxicity of pesti-
  cides to wildlife.  U.S. Fish and Wildlife Serv., Bur. Sport Fish
  Wildl. Resource Publ. #84.
Upshall, D. G., J.  C. Roger and J. E. Casida; 1968.  The teratogenic
  action of Bidrin and other neuroactive agents in developing hen eggs.
  Biochem. Pharmacol. 17:1539-1542.
Van Middelem, C. H., D. H. Habeck and J. R. Strayer; 1972.  Residues
  on ryegrass following preplant or postemergence applications of four
  insecticides for mole cricket control.  J. Econ. Entomol. 65:495-497.
Vicario, B. T.; 1972.  Effect of pesticides (2,4-D ester, Agroxone 4,
  and malathion) on the phosphorus, potassium, calcium and total ni-
  trogen levels.  Araneta Res. J. 19:103-114.
                                   529
-------
Voerman, S. and A. F. H. Besemer; 1970.  Residues of dieldrin, lindane,
  DDT and parathion in a light sandy soil after repeated application
  throughout a period of 15 years.  J. Agr. Food Chem. 18:717-719.
Vondell, J. H.; 1958.  Diazinon, its effect on egg quality and produc-
  tion.  Poultry Sci. 37:979-980.
Walker, N. E.; 1971.  Effect of malathion and malaoxon on esterases and
  gross development of the chick embryo.  Toxicol. Appl. Pharmacol. 19:
  590-601.
Walker, W. W. and B. J. Stojanovic; 1973.  Microbial versus chemical
  degradation of malathion in soil.  J. Environ. Qual. 2:229-232.
Walker, W. W. and B. J. Stojanovic; 1974.  Malathion degradation by
  Artkrobactex1 species.  J. Environ. Qual. 3:4-10.
Ware, G. W., B. Esteson and W. P. Cahill; 1972.  Organophosphate resi-
  dues on cotton in Arizona.  Bull. Environ. Contain. Toxicol. 8:361-
  362.
Way, M. J. and N. E. A. Scopes; 1965.  Side effects of some soil-app-
  lied systemic insecticides.  Ann. Appl. Biol. 55:340-341.
Way, M. J. and N. E. A. Scopes; 1968.  Persistence and effects on soil
  fauna of some soil-applied systemic insecticides.  Ann. Appl. Biol.
  62:199-214.
Weber, R. P., J. M. Coon and A. J. Triolo; 1974.  Effect of the organo-
  phosphate insecticide parathion and its active metabolite paraoxon on
  the metabolism of benzo(a)pyrene in the rat.  Cancer Res. 34:947-952.
Weidhass, D. E., M. C. Bowman and C. H. Schmidt; 1961.  Loss of para-
  thion and DDT to soil from aqueous dispersions and vermiculite gran-
  ules.  J. Econ. Entomol. 54:175-177.
Williams, C. H., J. L. Casterline, Jr., K. H. Jacobson and J. E. Keys;
  1967.  Studies of toxicity and enzyme activity resulting from inter-
  action between chlorinated hydrocarbon and carbamate insecticides.
  Toxicol. Appl. Pharmacol. 11:302-307.
Wilson, H. A.; 1954.  The effect of certain pesticides on nitrification
  in the soil.  Soils and Fertilizers 17:502.
                                  530
-------
Wilson, B. W., H. 0. Stinnett, D. M. Fry and P. S. Nieberg; 1973.
  Growth and metabolism of chick embryo muscle cultures.  Inhibition
  with malathion and other organophosphorus compounds.  Arch. Environ.
  Health 26:93-99.
Winterlin, W., J. B. Bailey, L. Langbehn and C. Mourer; 1975.  Degra-
  dation of parathion applied to peach leaves.  Pest. Monit. J. 8:263-
  269.
Wolfe, H. R., D. C. Staiff, J. F. Armstrong and S. W. Comer; 1973.
  Persistence of parathion in soil.  Bull. Environ. Contam. Toxicol.
  10:1-9.
Wolfe, N. L., R. G. Zepp, G. L. Baughman and J. A. Gordon; 1975.  Kine-
  tic investigation of malathion degradation in water.  Bull. Environ.
  Contam. Toxicol. 13:707-713.
Yamada, A.; 1972.  Teratogenic effects of organophosphorus insecticides
  in the chick embryo.  Osaka Shiritsu Daigaku Igaku Zasshi 21:345-355.
  (Chem. Abstr. 79:62350d, 1973).
Yamauchi, M., I. Muta and R. Sato; 1959.  Chemical studies on organo-
  phosphorus insecticides.  XI. Effect of additions on the decomposi-
  tion of malathion.  Botyu-Kagaku 24:168-173. (Chem. Abstr. 60:7384f,
  1964).
Yang, R. H. S., W. C. Dauterman and E. Hodgeson; 1969.  Enzymic degra-
  dation of diazinon by rat liver microsomes.  Life Sci. 8:667-672.
Yaron, B. and S. Saltzman; 1972.  Influence of water and temperature
  on adsorption of parathion by soils.  Soil Sci. Soc. Amer., Proc.
  36:583-586.
Yaron, B., B. Heuer and Y. Birk; 1974.  Kinetics of azinphosmethyl
  losses in the soil environment.  J. Agr. Food Chem. 22:439-441.
Yaron, B., H. Bielorai and L. Kliger; 1974b.  Fate of insecticides in
  an irrigated field:  azinphosmethyl and tetradifon cases.  J. Envi-
  ron. Qual. 3:413-417.
Yasue, Y.; 1956.  Influence of insecticides upon the development of
                                  531
-------
  certain bacteria.  Rept. Ohara Inst. Agr.  Biol. 44:51-55. (Chem.
  Abstr. 51:6925g, 1957).
Yasuno, M., S. Hirakoso, M. Sasa and M. Uchida; 1966.   Inactivation of
  some organophosphorus insecticides by bacteria in polluted water.
  Japan. J. Exptl. Med. 35:545-563. (Chem.  Abstr. 65:1324f, 1966).
Yu, C-C. and J. R. Sanborn; 1975.  Fate of parathion in a model eco-
  system.  Bull. Environ. Contain. Toxicol.  13:543-550.
Yurovskaya, E. M. and V. A. Zhulinskaya; 1974.   Behavior or organophos-
  phorus insecticides in the soil.  Khim. Sel.  Khoz. 12:358-361. (Chem.
  Abstr. 81:59300y, 1974).
Zhavoronkov, N. I., A. V. Akulov, S. D. Antsiferov, A. P. Verkhovskii,
  and S. M. Evdokimov; 1973.  Effect of carbamates on hens.  Veteri-
  nariya 1973:114-116. (Chem. Abstr. 79:122422r, 1973).
Zuckerman, B. M., C. W. Miller, R. M. Devlin, W. E. Tomlinson and R. L.
  Norgren; 1966.  Parathion studies on bean growth in sterile root cul-
  ture.  J. Econ. Entomol. 59:1157-1160.
Zuckerman, B. M., K. H. Deubert, M. Mackiewicz and H.  B. Gunner; 1970.
  Biodegradation of parathion.  Plant Soil 33:273-281.
                                  532
-------
CARBAMATE INSECTICIDES
Carbaryl
Carbaryl is the common name for 1-naphthyl W-methyl carbamate, intro-
duced by the Union Carbide Corporation in 1956 as Sevin.  A contact
insecticide with slight systemic properties, carbaryl is made by reac-
tion of 1-naphthol and methyl isocyanate or by reacting 1-naphthol with
phosgene and then methylamine.  It is a white crystalline solid with
a melting point of 142 C, a vapor pressure of 0.005 mm mercury at 26 C,
and a water solubility of less than 0.1 percent (1,000 ppm) at room
temperature.  It is soluble in most polar organic solvents such as di-
methyl sulfoxide.
Degradation-
Biological—The degradation of carbaryl by microorganisms is summarized
in Tables 81 and 82 and the pathways are shown in Figure 17.  The de-
gradation to 1-naphthol proceeds by hydrolysis, hydroxylation and pos-
sibly also by conjugation (Mehendale and Dorough 1972).  Bollag and
Liu (1971) noted that 1-naphthol is both more toxic and more persis-
tent than carbaryl itself.  Degradation of carbaryl to CO  and coumarin
has been reported for Pseudomonas (Kazano e£ j|l.. 1972).  Bollag and
Liu (1971) reported that Fusarium solani degraded 1-naphthol more rea-
dily than carbaryl, and that filamentous fungi were more effective than
bacteria.  Of 11 microorganisms tested, three were completely unable
to degrade carbaryl (Sikka et al. 1975).  Trichoderma vivide decomposed
                3
11.3 percent of  H-carbaryl, but only 2.1 percent of the label was
water-soluble (Matsumura and Boush 1968) .  Aspevgillus terr>eus degraded
carbaryl when it was present at 50 to 100 ppm, but was completely in-
hibited by 200 to 500 ppm.  The pyrethrin-synergizing methylenedioxy-
phenyl compounds, Sesamex and Sesamol, also decreased the rate of car-
                                  533
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1,2-DIHYROXYNAPHTHALENE


             \*
-------
baryl degradation by Aspergillus  (Bollag and Liu 1974).  An Aehromo-
baoter species converted carbaryl to 1-naphthol, hydroquinone and cate-
chol pyruvate in the absence of other sources of carbon (Sud et al.
1972).  Pseudomonas melophthora, a symbiote of the apple maggot, con-
                      3
verted 6.4 percent of  H-carbaryl to water-soluble metabolites and 45.5
percent to solvent-soluble metabolites (Boush and Matsumura 1967) while
another symbiote, Bacillus cereus, reportedly also degraded carbaryl
(Singh 1974).
     14
When   C-1-naphthol was added to cultures of bacteria in river water,
                                              14
44 percent of the 1-naphthol was converted to   C-carbon dioxide with-
in 60 hours.  Seventeen percent of the radioactivity remained in the
growth medium, and 22 percent was associated with the bacteria.  The
major residue was 4-hydroxy-l-tetralone, and bacterial growth was com-
pletely inhibited by more than 100 ppm of 1-naphthol (Bollag et al.
1975).
Metabolism of carbaryl in plants may consist of little more than in-
activation; alternatively, oxidation or hydroxylation of the ff-methyl
group may be followed by ring degradation (Kuhr 1968).
In fish (Cyprinus earpio"), Ishii and Hashimoto (1970) reported com-
plete degradation of carbaryl, with no 1-naphthol detectable after 24
hours.  In cows, 1-naphthol and conjugated metabolites of carbaryl
were excreted in the urine and feces, but not in milk, when cows were
fed 450 ppm of technical carbaryl for fourteen days.  Urinary excretion
ended within four days of the last exposure to carbaryl, and even in-
gestion of 12 ppm of 1-naphthol did not result in tainted milk (White-
hurst et al. 1963).  Rat intestines converted carbaryl to napthyl glu-
curonide in vitro (Pekas 1971).
In human embryonic lung cells in culture, carbaryl was almost completely
metabolized within 72 hours.  The major metabolites were 1-naphthol,
4-hydroxycarbaryl, 5-hydroxycarbaryl, and 5,6-dihydroxycarbaryl.  Un-
known compounds and conjugates were also produced (Lin et al. 1975).
                                   537
-------
In mice, both 4-hydroxycarbaryl and 5-hydroxycarbaryl are rapidly con-
jugated to form 2>e£a-D-glucosides, which are significantly less toxic
to the animals (Cardona and Borough 1975).
Chemical and physical—Treatment with liquid ammonia and metallic so-
dium or lithium destroyed 92.8 and 93.5 percent of analytical grade
carbaryl, respectively, but the decomposition products were not iden-
tified (Kennedy et^ al.  1972a).  Treatment with I6N nitric acid resulted
in formation of nitrobenzene; 15 N ammonium hydroxide only resulted in
conversion to 1-naphthol (Kennedy et_ a]^. 1972b) .  In soil, nonbiologi-
cal hydrolysis of carbaryl to 1-naphthol has been shown to occur (Ka-
zano et_ al. 1972) .
Thermal degradation of  carbaryl in commercial formulation was 88.7 per-
cent effective at 600 C, and 89.5 percent effective in a dry combustion
furnace at 1,000°C (Kennedy et_ a^. 1969).  Volatile products of car-
baryl combustion at 900 C included carbon monoxide, carbon dioxide,
hydrochloric acid,  ammonia, and oxygen, as well as unidentified pro-
ducts (Kennedy et_ al. 1972a, 1972b) .
Photolytic—Ultraviolet light decomposed carbaryl primarily by cleav-
age of the ester bond (Aly and El-Dib 1971, Fedorova and Karchik 1970).
Further photolytic studies demonstrated that some degradation products
were also cholinesterase inhibitors and that the nature of the degra-
dation depended on formulation (Crosby et al. 1965).  Moisture (Fedor-
ova and Karchik 1970) and high pH (Aly and El-Dib 1971) accelerated
photolysis of carbaryl.
Transport-
Within soil—Carbaryl was less readily adsorbed to pond sediments and
watershed soils than either malathion or phorate (Meyers et al. 1970).
After 1,000 liters/ha of three percent Sevin were applied to soil, 51.5
to 58.1 percent of the original level of carbaryl was detected between
zero and five centimeters after five days; residues were detected at
                                   538
-------
depths of 50 to 60 centimeters for 15 to 20 days (Nalbandyan 1974).
Adsorption of carbaryl to soil organic matter surfaces is probably
physical rather than chemical, depends on the saturating cation and in-
creases with increasing temperature between 5  and 40 C (Leenheer and
Ahlrichs 1971).
Between soil and water—No data were available on the transport of
carbaryl or its major metabolite, 1-naphthol, through or with soil
into water, or from water into sediments.
Into air—Loss of carbaryl from petri dishes after 12 days exposure to
a constant air flow of ten cubic feet per hour was 1.6 mg at a relative
humidity of three to 13 percent, and 6.2 mg at a relative humidity of
75 to 85 percent, but the amounts originally exposed were not given
(Lyon and Davidson 1965) .
Into organisms—Carrots contained less carbaryl than either parathion
or diazinon after fields were treated with two or three times the nor-
mal agricultural levels of each chemical (Stobwasser 1963) .
In the subarctic, residues of carbaryl one month after application of
five kg/ha (2.2 ppm) were 0.1 ppm in soil, 0.5 ppm in lichens, 0.6 ppm
in arctic birds, 1.4 ppm in lemming livers, 1.5 ppm in woodcock livers,
and ten ppm in the testes of small mammals (Shilova et al_. 1973).  Kurtz
and Studholme (1974), however, found little uptake of carbaryl in song-
birds after forests were sprayed for gypsy moths, and no carbaryl resi-
dues were present in cattle after seven days, although milk excretion
persisted for over 60 hours (Hurwood 1967).  Organ retention of carba-
ryl in mice lasted two days after doses of 50 mg/kg; in rabbits, six
days after doses of 400 mg/kg; and in chickens, five days after 1,500
mg/kg (Ryamushkin and Yakub 1971).
Persistence-
Carbaryl applied as a termiticide retained 60 to 100 percent of its
effectiveness for four years (Beal and Smith 1972).  Ivanova and
                                  539
-------
Molozhanova (1974) postulated an exponential decrease in soil levels
of carbaryl with time; empirically, the rate of loss was:
                    1/k = 16.9 x + 15.3 pH - 46.24
where x is equal to the humus content of the soil.
In river water exposed to natural and artificial light in jars, 95 per-
cent of ten g/liter (10,000 ppm) of carbaryl decomposed x^ithin one
week, and no carbaryl was detected after two weeks  (Eichelberger and
Lichtenberg 1971).  In laboratory aquaria, the "half-life" of carbaryl
in seawater without mud was 38 days at 8 C, but at  20 C, 43 percent
was converted to 1-naphthol in 17 days.  When mud was included in the
aquaria, less than ten percent of the carbaryl was  converted to 1-naph-
thol after ten days.  In a natural mud flat, carbaryl persisted for
42 days, 1-naphthol for only one day (Karinen et_ aJU 1967).
Soil residues one month after five kg/ha were applied to soil in the
subarctic were 0.1 mg/kg (0.1 ppm)  (Shilova et^ al_. 1973).  Kazano et_
al. (1972) noted that 1-naphthol was chemically bonded to the humus in
soil and was stable to alkali.
Effect on Non-Target Species-
Microorganisms—In the laboratory, while 20 yg/ml (20 ppm) inhibited
growth of Fusariwn oxysporum, the effects could be  prevented by yeast
extracts, asparagine, ammonium nitrate, or ammonium sulfamate, but not
by vitamins.  None of the 17 fungi tested was able  to grow with carba-
ryl as the sole source of carbon (Cowley and Lichtenstein 1970).  Jaku-
bowska and Novak (1973) reported significant inhibition of fungal
growth by carbaryl, but in another study carbaryl stimulated fungal
growth (Askerov 1969).  Algae and bacteria varied in their response, as
summarized in Tables 83 and 84.  Carbaryl in sandy  soil produced a
greater effect on microorganisms than in either chernozem or peat
(Brantsevich et_ al_. 1973).
Invertebrates—The acute LPrn of carbaryl to honeybees was 0.02 per-
cent, or 200 ppm, under laboratory conditions.  Under the experimental
                                  540
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conditions used, carbaryl was less toxic to bees than parathion, diel-
drin, or azinphosmethyl, but more toxic than phorate or DDT  (Johansen
1961).  In pasture, carbaryl reduced the biomass of earthworms by as
much as 60 percent, and their numbers by as much as 68 percent (Thomp-
son 1970); straw decomposition was delayed by 6.5 to 17.6 percent be-
cause of carbaryl toxicity to the earthworms AlloZophoTba caliginosa
(Atlavinyte e_t al. 1974).
At 2.3 and 4.6 kg/ha on intertidal mud flats, carbaryl decreased the
numbers of juvenile clams (Tresus oapax, Macoma masuta, Callianassa
aaliforniensis'), but did not appear to reduce the numbers of polychaete
or nemertean worms (Armstrong and Milleman 1974).  The harvest of
Louisiana red crawfish, Procambarus olarkii3 was unaffected by carba-
ryl at agricultural levels (Hendrick et al. 1966) .
In an aquatic ecosystem (Kanazawa et al. 1975), carbaryl was character-
ized as relatively persistent when it was applied to air-dried soil,
after which water and aquatic organisms were added.  Most of the car-
baryl (68 percent) remained in the soil: 0.11 to 1.59 percent was
taken up by the catfish, crawfish, daphnids, algae, and duckweed.  No
toxicity was associated with the soil-bound carbaryl, 45 percent of
which was not extractable by solvents or methanol (Kanazawa et al.
1975).
In an aquatic-terrestrial model ecosystem  (Metcalf et al. 1971) , no
carbaryl residues were found in any of the organisms, and the water
contained only degradation products.  Sanborn (1974) and Metcalf and
Sanborn (1975) concluded that carbaryl would not accumulate in aquatic
food chains.
Plants—Carbaryl increased the herbicidal persistence of CIPC (iso-
propyl m-chlorocarbanilate)  regardless of soil pF or soil type (Kauf-
man et al. 1970).  Propanil inhibited interconversion of carbaryl met-
abolites on leaves (Chang e_t al. 1971b) , and carbaryl inhibited the
                                  543
-------
metabolism of propanil in leaf tissue (Chang et al. 1971a) and in soil
(Kaufman et al. 1971) .  Chlorpropham and malathion stimulated the de-
gradation of carbaryl on leaves, but linuron inhibited it (Chang et_ al.
1971b).
On grain sorghum, agricultural levels of carbaryl were not phytotoxic
(Meisch _et_ al. 1970) .  Soaking cotton seeds (Gossypiim barbadense) in
carbaryl for one to  three days decreased seed germination, but weekly
sprays of a 50 percent saturated solution increased both abscission
and cotton yields per plant (Hammouda et al. 1966) .
At 1,500 ppm, carbaryl decreased the germination of barley (Eordeym
Vulgare) by 52 percent, and induced chromosome aberrations in root tip
cells (Wuu and Grant 1966) .  Chromosome aberrations were induced in
beans (V-Ceia faba) by spraying plants with carbaryl daily for eight
days.  Pollen sterility was not induced, but the chromosome damage was
dose-dependent (Amer and Farah 1968) .
Fish — The 24-hour LC^ of carbaryl to fish ranged from 1.75 ppm for
longnose killifish  (Fundulus similis) to 6.7 ppm for three-spine stick-
lebacks (Gasierosteus aculeatus) , while the 96-hour LC   ranged from
0.76 ppm in coho salmon (Oncorhynehus kisuteh) to 20 ppm in black bull-
heads, (Ictalurus melas) .  Some data suggest that sub-clinical levels
of carbaryl lowered the natural resistance of fish to parasites (Pim-
entel 1971).
Birds — The acute oral LD,.- of carbaryl in Japanese quail (Cotuvn-ix ao-
       japoniaa) was 2,290 mg/kg and in mallards (Anas platyrh-inohos)
more than 2,179 mg/kg (Tucker and Crabtree 1970).  In 39 day old Japan-
ese quail, liver levels of vitamin A were decreased in females but not
in males  (Cecil et al. 1974).  The acute oral LDC_ in male chicks was
                — —                           jU
197 mg/kg, with 95 percent confidence limits ranging from 154 mg/kg to
250 mg/kg (Sherman and Ross 1961) , but Zhavoronkov &t_ a^ . (1973) claim-
ed that after feeding one percent of the LD   to hens for ten days,
development of their chicks was impaired.
                                  544
-------
When 3.44 rag/embryo of carbaryl was  injected into  the allantoic  cavity,
50 percent of chick embryos died, but the survivors exhibited no his-
topathologic changes, even when 6.75 mg/embryo were injected  (Tos-Luty
et al. 1973).  Olefir and Vinogradova (1968) reported numerous malfor-
mations in chick embryos after 0.064 mg/kg carbaryl were  injected  into
the yolk sac.  Dunachie and Fletcher (1969) observed malformations,
mainly of the feathers, in chicks treated with 50  ppm carbaryl injected
into the yolk.
Mammals—The acute oral LD   of carbaryl in rats is between 40 mg/kg
(Jones et_ al.. 1968) and 540 mg/kg (Metcalf et_ al.  1962) .  Yakin  (1967)
cited an acute oral LD,-_ of 721 mg/kg for rats and 150 mg/kg  for cats.
Since rats survived daily injection  of five percent of  the LD^  for at
least six months, Yakin (1967) considered carbaryl no more than mildly
cumulative.  Pretreatment with DDT decreased the toxicity of  carbaryl
to mice (Meksongsee et_ al. 1967) .
Numerous reports suggest that carbaryl exerts a considerable  effect on
cellular enzymes (Khaikina 1970, Orlova 1970, Kagan e_t al. 1970, Kuz'-
minskaya and Yakushko 1970, Kuz'minskaya 1971), on the  immune response
(Olefir 1971), and causes cardiovascular disturbances (Orzel  and Weiss
1966, Kagan et_ _a2L. 1970, 1973, 1974; Lukaneva and  Rodionov 1973).  In
tissue culture, carbaryl was more toxic than its metabolite 1-naphthol
(Litterst and Lichtenstein 1971).  Lower concentrations of carbaryl
stimulated the growth of HeLa cells, but at higher concentrations  growth
was inhibited (Blevins and Dunn 1975).  Two percent of  the LD  » given
daily for thirty days, altered the exocrine activity of the pancreas
(Urbanowicz et al. 1973) .
Reproductive disturbances in rats have been reported at chronic  treat-
ment with no more than 50 mg/kg/day  (Shtenberg et  al. 1970, Shtenberg
and Ozhovan 1971, Przezdziecki et^ a!U 1974, Trifonova et_  &L_.  1970).  Em-
bryotoxic effects were also reported by several authors (Shtenberg et
al. 1973, Tos-Luty et_ al. 1974, Torchinskii 1974).  In a  three-genera-
                                   545
-------
tion study, chronic feeding of 2,000 ppm decreased the reproductive
fitness of both rats and gerbils (Collins et^ al_. 1971).  In mice, no
significant effects on reproduction were observed when ten mg/kg of
carbaryl were fed for three generations, and even 500 mg/kg produced
no significant effects except an increase in pre-weaning mortality.
Administration of 100 mg/kg by intubation before mating did, however,
reduce fertility (Weil et_ aJL. 1972).
Carbaryl was not teratogenic in guinea pigs at 300 mg/kg, in hamsters
at 250 mg/kg, or in rabbits at 200 mg/kg (Robens 1969).  Carbaryl is
not teratogenic in rats (Shtenberg and Torchinskii 1972, Weil et al.
1973).  In beagle dogs, Smalley and co-workers (1968) observed malfor-
mations at carbaryl levels of 50 mg/kg, but no dose-response relation-
ship was evident.  There was no evidence of chromosome damage in mice
injected intraperitoneally with 20 mg/kg of carbaryl (Jordan et al.
1975) and no increase in resistance to carbaryl after 12 to 14 genera-
tions of selection (Guthrie et al. 1971).
Makovskaya and co-workers (1965) reported fatty necrotic areas in the
livers and spleens of mice treated with 60 mg/kg carbaryl for six
months; no tumors were found even after 20 months.  Zabezhinski (1970)
claimed that beta-Sev±n caused "cancerous tumors" when given orally
or intravenously, but no dosage level was reported.  Carbaryl can also
serve as a precursor to the potent bacterial mutagen, nitrosocarbaryl
(Elespuru et^ al_. 1974, Siebert and Eisenbrand 1974) which could plaus-
ibly be formed within the human digestive system (Uchiyama et al. 1975) .
Mild, permanent, and increasing functional deviation was observed in
the nervous system of maze-trained rats treated with subacute levels
of carbaryl (Desi et^ al. 1974).
Conclusions-
Inasmuch as both carbaryl and its major metabolite 1-naphthol are rea-
dily decomposed by microorganisms, soil disposal of carbaryl is feasible.
                                   546
-------
Metalkamate
Metalkamate, more commonly referred to as Bux, is a mixture of three
parts 777- (l-methylbutyl)-phenyl /7-methylcarbamate and one part of
m-(l-ethylpropyl)-phenyl /^-methylcarbamate, introduced by Chevron
Chemical Company in 1966 under the trade names of Ortho 5353 and Bux.
Metalkamate is a colorless solid with a melting point of 45 to 50 C.
It is soluble in water to less than 50 ppm, but readily soluble in
xylene and methanol.  Bux is formulated as ten percent clay granules,
and is used primarily against corn rootworm larvae (Tucker 1973).
Degradation-
Tucker and Pack (1972) analyzed the degradation of metalkamate in soil
under laboratory conditions and concluded that microbial degradation
predominated, since degradation was more rapid in unsterilized than in
sterile soil.  In unsterilized soil, 50 percent of the metalkamate was
degraded within one week and in sterilized soil, five to fifteen per-
                                        14                   14
cent was degraded in the same time with   C0« evolution from   C-car-
bonyl-labeled metalkamate.  In additional studies on the major compo-
nent, m-(l-methylbutyl)-phenyl ff-methylcarbamate, the major metabolite
was m-(l-hydroxy-l-methylbutyl)-phenyl A7-methylcarbamate.
Metalkamate is stable in neutral or acidic media, but under alkaline
conditions it is hydrolyzed to the respective phenols, carbon dioxide,
and methylamine (Tucker 1973).  No data were available on the photo-
lysis or physical degradation of metalkamate.
Transport-
No data were available on the movement of metalkamate in soil, between
soil and water, or on losses due to volatilization.
In an aquatic-terrestrial model ecosystem, metalkamate did not show
any tendency to accumulate in the higher members of the trophic web.
                                  547
-------
The alga and Elodea contained residues of 0.98 ppm and 0.24 ppm, res-
pectively, of the parent compound; and the crab, which died seven days
after the addition of metalkamate, contained 0.05 ppm.  The other or-
                                           14
ganisms contained no detectible amounts of   C.  Yu et_ al. (1974) and
Metcalf and Sanborn (1975) concluded that metalkamate would not lead
to environmental problems of accumulations in the food chain.
Persistence-
Harris (1973) considered metalkamate to be a moderately persistent
soil insecticide which lost its insecticidal activity within 16 weeks.
Metalkamate was less toxic to crickets when soil-applied than as a
direct contact insecticide, but the inactivation was only moderate in
moist sand.  In muck, activity against crickets was reduced by a fac-
tor of fifty in comparison to direct toxicity (Harris, 1973).  Degra-
dation of metalkamate in solution was 50 percent complete in silt or
silt loam soil in one week under laboratory conditions.  The authors
concluded that slower degradation would occur under field conditions
since Bux is applied as granules (Tucker and Pack 1972).
Effects on Non-Target Species-
No data were available on the effects of metalkamate on soil processes
or soil microorganisms.  Apple (1971) considered Bux sufficiently phy-
totoxic that in-row application at the rate of one pound per acre might
injure corn with damage depending on climatic conditions in the days
following planting.  Bux applied at one pound per acre reduced the num-
bers of earthworms in pasture severely (Thompson 1970), but recovery
occurred within one year (Thompson and Sans 1974).  The acute oral LD
of Bux is 87 mg/kg in rats, and the acute dermal LD,._ is 500 mg/kg
(Anonymous 1974).
Conclusions-
Metalkamate is toxic to earthworms in pasture (Thompson 1970, Thompson
and Sans 1974), is phytotoxic to corn at approximately 2 ppm, or 1 Ib/A
                                  548
-------
(Apple 1971), and appears to be highly toxic to crabs (Metcalf and San-
born 1975).
In the absence of data on its transport within soil and from soil to
water, soil disposal of metalkamate wastes is not recommended.  Prior
treatment by chemical hydrolysis to the phenols before soil disposal
might greatly enhance the degradation, but the consequences are merely
speculative.
                                  549
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References
Aly, 0. M. and M. A. El-Dib; 1971.  in:  Org.  Compounds Aquatic Environ.j
  Rudolfs Res. Conf.3 5th.   1969.  pp. 469-493.  Faust, S. J., ed.;
  Dekker, N. Y.  Photodecomposition of some carbamate insecticides in
  aquatic environments.  (Chem. Abstr. 77:110350m, 1972).
Amer, S. M. and 0. R. Farah; 1968.  Cytological effects of pesticides
  III. Meiotic effects of 1-naphthyl ^-methylcarbamate, Sevin.  Cyto-
  logia 33:337-344.
Anonymous; 1974.  Entomology Fact Sheet:  Check list of insecticides.
  University of Illinois, Cooperative Extension Service.
Apple, J. W.; 1971.  Response of corn to granular insecticides applied
  to the row at planting.  J. Econ. Entomol. 64:1208-1211.
Armstrong, D. A. and R. E.  Millemann; 1974.  Effects of the insecti-
  cide carbaryl on clams and some other intertidal mud flat animals.
  J. Fish Res. Board Can. 31:466-470.
Askerov, N. A.; 1969.  Effect of insecticides on the number of some
  groups of soil microorganisms.  Biol. Zh. Arm. 22:106-107.  (Chem.
  Abstr. 71:122761k, 1969).
Atlavinyte, 0., J. Daciulyte and A. Lugauskas; 1974.  Biological acti-
  vity of soil during straw humification in it.  2. Effect of herbi-
  cides and insecticides on the densities and activity of soil organisms.
  Liet. TSR Mokslu Akad. Darb., Ser. C. (4):47-56. (Chem. Abstr. 83:
  73036g, 1975).
Beal, R. H. and V. K. Smith; 1972.  Carbamate or phosphate insecti-
  cides for subterranean termite control.  Pest Contr. 40(7):20, 22,
  43.
Blevins, R. D. and W. C. Dunn, Jr.; 1975.  Effects of carbaryl and
  dieldrin on the growth, protein content, and phospholipid content of
  HeLa cells.  J. Agr. Food Chem. 23:377-382.
                                  550
-------
Bollag, J. M. and S. Liu; 1971.  Degradation of Sevin by soil micro-
  organisms.  Soil Biol. Biochem. 3:337-345.
Bollag, J. M. and K. C. Liu; 1974.  Effect of methylenedioxyphenyl
  synergists on metabolism of carbaryl by Aspergittus teweus.  Ex-
  perientia 30:1374-1375.
Bollag, J. M., E. J. Czaplicki and R. D. Minard; 1975.  Bacterial meta-
  bolism of 1-naphthol.  J. Agr. Food Chem. 23:85-90.
Boush, G. M. and F. Matsumura; 1967.  Insecticidal degradation by
  Pseudomonas meolphthora, the bacterial symbiote of the apple maggot.
  J. Econ. Entomol. 60:918-920.
Brantsevich, L. G., E. G. Molozhanova and L. B. Remizova; 1973.  Effect
  of Sevin as an insecticidal preparation on soil microflora.  Fiziol.
  Aktiv. Veshchestva 5:127-129. (Chem. Abstr. 81:10295m, 1974).
Cardona, R. A. and H. W. Borough; 1973.  Syntheses of the beta-T>-gl.u-
  cosides of 4- and 5-hydroxy~l-naphthyl-/l7-methylcarbamate.  J. Agr.
  Food Chem. 21:1065-1071.
Cecil, H. C., S. J. Harris and J. Bitman; 1974.  Effects of nonpersis-
  tent pesticides on liver weight, lipids and vitamin A of rats and
  quail.  Bull. Environ. Contain. Toxicol. 11:496-499.
Chang, F., L. W. Smith and G. R. Stephenson; 1971a.  Insecticide inhi-
  bition of herbicide metabolism in leaf tissues.  J. Agr. Food Chem.
  19:1183-1186.
Chang, F., G. R. Stephenson and L. W. Smith; 1971b.  Influence of her-
  bicides on insecticide metabolism in leaf tissues.  J. Agr. Food
  Chem. 19:1187-1190.
Chen, K. S., B. R. Funke and J. T. Schulz; 1974.  Effects of certain
  organophosphate and carbamate insecticides on Baaillus thurigiensis.
  J. Econ. Entomol. 67:471-473.
Christie, A. E.; 1969.  Effects of insecticides on algae.  Water Sew-
  age Works 116:172-176.
Collins, T. F. X., W. H. Hansen and H. V. Keeler; 1971.  Effect of car-
  baryl (Sevin) on reproduction of the rat and gerbil.  Toxicol. Appl.
                                  551
-------
  Pharmacol. 19:202-216.
Cowley, G. T. and E. P. Lichtenstein; 1970.  Growth inhibition of soil
  fungi by insecticides and annulment of inhibition by yeast extract:
  or nitrogenous nutrients.  J. Gen. Microbiol. 62:27-34.
Crosby, D. G. , E. Leitis and W. L. Wint.erlin; 1965.  Photodecomposi-
  tion of carbamate insecticides.  J. Agr. Food Chem. 13:204-207.
DeGiovanni-Donnelly, R., S. M. Kolbye and P. D. Greeves; 1968.  The
  effects of IPC, CIPC, Sevin, and Zectran on Bacillus subtilis.   Ex-
  perientia 24:80-81.
Desi, I., L. Gonczi, G. Simon, I. Farkas and Z. Kneffel; 1974.  Neuro-
  toxicologic studies of two carbamate pesticides in subacute animal
  experiments.  Toxicol. Appl. Pharmacol. 27:465-476.
Dunachie, J. F. and W. W. Fletcher; 1968.  Investigation of the toxi-
  city of insecticides to birds' eggs using the egg-injection tech-
  nique.  Ann. Appl. Biol. 64:409-423.
Eichelberger, J. W. and J. J. Lichtenberg; 1971.  Persistence of pes-
  ticides in river water.  Environ. Sci. Technol. 5:541-544.
Elespuru, R. , W. Lijinsky and J. K. Setlow; 1974.  Nitrosocarbaryl as
  a potent mutagen of environmental significance.  Nature 247:386-387.
Fedorova, Yu. N., and 0. N. Karchik; 1970.  Effect of external factors
  on the decomposition of Sevin.  Khim,  Sel. Khoz. 8:762-764. (Chem..
  Abstr. 71:41415k, 1971).
Gaur, A. C. and K. C. Misra; 1970.  Effects of insecticides on soil
  microorganisms.  Pesticides 4:24-27. (Chem. Abstr. 73:108697d, 1970).
Guthrie, F. E., R. J. Monroe and C. 0. Abernathy; 1971.  Response of
  laboratory mouse to selection for resistance to insecticides.  Toxi-
  col. Appl. Pharmacol. 18:92-101.
Hammouda, M. A., S. M. Amer and 0. R. Farah; 1966.  The effect of 1-
  naphthyl ^l/-methylcarbamate, Sevin, on germination, growth and yield
  of the cotton plant.  Flora  (Jena), Abt. A. 157:292-298.  (Chem.
  Abstr. 66:75240z, 1967).
                                  552
-------
Harris, C. R. ; 1973.  Laboratory evaluation of candidate materials as
  potential soil insecticides.  IV. J. Econ. Entomol. 66:216-221.
Hendrick, R. D., T. R. Everett and H. R. Caffey; 1966. Effects of some
  insecticides on the survival, reproduction, and growth of the Louis-
  iana red crawfish.  J. Econ. Entomol. 59:188-192.
Hurwood, I. S.; 1967.  Studies on pesticide residues.  II.  Carbaryl
  residues in the body tissues and milk of cattle following dermal
  application.  Queensland J. Agr. Anim. Sci. 24:69-74.
Ishii, Y. and Y. Hashimoto; 1970.  Metabolic fate of carbaryl (1-naph-
  thyl //-methylcarbamate) orally administered to Cypvinus carpio
  (carp).  Noyaku Kensasho Hokoku No. 10:48-50. (Chem. Abstr. 75:18847q,
  1971).
Ivanova, L. N. and E. G. Molozhanova; 1974.  Kinetics of the transfor-
  mation of some pesticides in the soil.  Khim. Sel. Khoz. 12:363-365.
  (Chem. Abstr. 81:73363c, 1974).
Jakubowska, B. and A. Nowak; 1973.  Effect of certain phosphoroorganic
  insecticides and carbamates on growth of soil fungi.  Zescz. Nauk.,
  Akad. Roln. Szczecinic 10:14-50. (Chem. Abstr. 81:115584h, 1974).
Johansen, C. A.; 1961.  Toxicity of certain insecticides to honeybees
  in the laboratory.  J. Econ. Entomol. 54:1008-1009.
Jones, K. H., D. M. Sanderson and D. N, Noakes; 1968.  Acute toxicity
  data for pesticides.  World Rev. Pest. Contr. 7:135-143.
Jordan, M. , Z. Srebro, E. Piersciriska and L. Woz'ny; 1975.  Preliminary
  observations on the effects on the organs of mice of administering
  some carbamate pesticides.  Bull. Environ. Contain. Toxicol. 14:205-
  208.
Kagan, Y. S., I. M. Trakhtenberg, G. A. Rodionov, A. M. Lukaneva, L. Y.
  Voronina and G. E. Verich; 1973.  Effect of pesticides on the onset
  and development of certain pathological processes.  Gig. Sanit. 1973,
  (3):23-27. (Chem. Abstr. 81:22025m, 1974).
Kagan, Y. S., A. M. Lukaneva and G. A. Rodionov; 1974.  Effect of pes-
  ticides on the development of some kinds of experimental pathology of
  the cardiovascular system.  Farmakol. Toksikol. 9:189-196.
                                  553
-------
  (Chem. Abstr. 82:11958n, 1975).
Kagan, Y. S., G. A. Rodionov, L. Y. Voronina, L. S. Velichko, 0. M.
  Kulagin and A. D. Peremitina: 1970.  Effect of Sevin on liver struc-
  ture and function.  Farmakol. Toksikol. (Moscow) 33:219-224.  (Chem.
  Abstr. 73:2944s, 1970).
Kanazawa, J., A. R. Isensee and P. C. Kearney; 1975.  Distribution of
  carbaryl and 3,5-xylylmethylcarbamate in aquatic model ecosystem.
  J. Agr. Food Chem. 23:760-763.
Karinen, J. F., J. G. Lamberton, N. E. Stewart and L. C. Terriere; 1967.
  Persistence of carbaryl in the marine estuarine environment.  Chemi-
  cal and biological stability in aquarium systems.  J. Agr. Food Chem.
  15:148-156.
Kaufman, D. D.; 1974.  in: Pesticides in Soil and Water.  133-202. W.
  D. Guenzi, ed.; Soil Sci. Soc. Am. Inc.; Madison, Wis., USA. Degra-
  dation of pesticides by soil microorganisms.
Kaufman, D. D., P. C. Kearney, D. W. Von Endt and D. E. Miller; 1970.
  Methylcarbamate inhibition of phenylcarbamate metabolism in soil.  J.
  Agr. Food Chem. 18:513-519.
Kaufman, D. D., J. Blake and D. E. Miller; 1971.  Methylcarbamates af-
  fect acylanilide herbicide residues in soil.  J. Agr. Food Chem. 19:
  204-206.
Kazano, H., P. C. Kearney and D. D. Kaufman; 1972.  Metabolism of
  methylcarbamate insecticides in soils.  J. Agr. Food Chem. 20:975-
  979.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1969.  Chemi-
  cal and thermal methods for disposal of pesticides.  Residue Reviews
  29:89-104.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman; 1972a.  Chemical
  and thermal aspects of pesticide disposal.  J. Environ. Qual. 1:63-
  69.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman; 1972b.  Analysis of
  decomposition products of pesticides.  J.  Agr. Food Chem. 20:341-343.
                                  554
-------
Khaikina, B. E.; 1970.  Mechanism of Sevin action on warm-blooded ani-
  mals.  Gig. Primen., Toksikol. Pestits. Klin. Otravlenii  No. 8:203-
  208. (Chem. Abstr. 77:122761j, 1972).
Ruhr, R. J.; 1968.  Metabolism of methylcarbamate insecticide chemicals
  in plants.  J. Sci. Food Agr.  (Suppl) 44-49.  (Chem. Abstr. 70:56657g,
  1969).
Kurtz, D. A. and C. R. Studholme; 1974.  Recovery of trichlorfon (Dy-
  lox) and carbaryl  (Sevin) in songbirds following spraying of forest
  for gypsy moth.  Bull. Environ. Contain. Toxicol. 11:78-84.
Kuz'minskaya, U. A.; 1971.  Mitochondria contractility under the effect
  of DDT and Sevin.  Farmakol. Toksikol. 34:232-235. (Chem. Abstr. 75:
  19186k, 1971).
Kuz'minskaya, U. A. and V. E. Yakushko; 1970.  Effect of DDT and Sevin
  on the activity of some liver enzymes.  Gig. Sanit. 35:97-99. (Chem.
  Abstr. 73:76076g, 1970).
Leenheer, J. R. and A. L. Ahlrichs; 1971.  Kinetic and equilibrium
  study of the adsorption of carbaryl and parathion upon soil organic
  matter surfaces.  Soil Sci. Soc. Amer., Proc. 35:700-705.
Lin, T. H., H. H. North and R. E. Menzer; 1975.  Metabolism of carba-
  ryl (1-naphthyl 7l/-methylcarbamate) in human embryonic lung cell cul-
  tures.  J. Agr. Food Chem. 23:253-256.
Litterst, C. L. and E. P. Lichtenstein; 1971.  Effects and interac-
  tions of environmental chemicals on human cells in tissue culture.
  Arch. Environ. Health 22:454-459.
Liu, S. and J. M. Bollag; 1971a.  Metabolism of carbaryl by a soil fun-
  gus.  J. Agr. Food Chem. 19:487-490.
Liu, S. and J. M. Bollag; 1971b.  Carbaryl decomposition to 1-naphthyl
  carbamate by Aspergillus terreus.  Pestic. Biochem. Physiol. 1:366-
  372.
Loboda, L. S.; 1970.  Laboratory evaluation of fungicides against fla-
  vinaceous dewy fungi.  Visn. Sil's'kogospod. Nauki 13:85-89. (Chem.
  Abstr. 73:54953p, 1970).
                                  555
-------
Lukaneva, A. M. and G. A. Rodionov; 1973.  Effect of DDT and Sevin on
  the development of cholesterol atherosclerosis.  Gig. Sanit. 1973:
  41-45. (Chem. Abstr. 80:23319b, 1974).
Lyon, W. F. and R. H. Davidson; 1965.  The effect of humidity on the
  volatilization of insecticides.  J. Econ. Entomol. 58:1037.
Makouskaya, E. I., M. B. Rapoport and V. G. Pinchuk; 1965.  Possible
  cancerogenic effect of some carbamate insecticides.  Vop. Eksp.
  Onkol. No. 1:67-74. (Chem. Abstr. 67:31897k, 1967).
Martin, H.; 1968.  Pesticide Manual.  British Crop Protection Council.
Matsumura,  F. and G. M. Boush; 1968.  Degradation of insecticides by a
  soil fungus, Trichoderma viride.   J. Econ. Entomol. 61:610-612.
Meisch, M.  V., G. L. Teetes, N. M.  Randolph and A. Bockholt; 1970.
  Phytotoxic effects of insecticides on six varieties of grain sorghum.
  J. Econ.  Entomol. 63:1516-1517.
Mehendale,  H. H. and H. W. Dorough; 1972.  Conjugative metabolism and
  action of carbamate insecticides.  Pestic. Chem., Proc. Int. Congr.
  Pestic. Chem., 2nd 1:15-28.
Meksongsee, B., R. S. Yang and F. E. Guthrie; 1967.  Effect of inhibi-
  tors and inducers of microsomal enzymes on the toxicity of carbamate
  insecticides to mice and insects.  J. Econ. Entomol. 60:1469-1471.
Metcalf, R. L. and J. R. Sanborn; 1975.  Pesticides and environmental
  quality in Illinois.  111. Nat. His. Survey Bull.
Metcalf, R. L., W. P. Flint and C.  L. Metcalf; 1962.  Destructive and
  Useful Insects.  McGraw Hill, N.  Y., N. Y.; 1087 pp.
Metcalf, R. L., G. K. Sangha and I. P. Kapoor; 1971.  Model ecosystem
  for the evaluation of pesticide biodegradability and ecological mag-
  nification.  Environ. Sci. Technol. 5:709-713.
Meyers, N.  L., J. L. Ahlrichs and J. L. White; 1969.  Adsorption of in-
  secticides on pond sediments and watershed soils.  Proc., Indiana
  Acad. Sci. 79:432-437.
Nalbandyan, R. A.; 1974.  Persistence of Sevin and Phosalone in the
  soil.  Zashch. Rast. (Moscow) 26. (Chem. Abstr. 81:73331r, 1974).
                                  556
-------
Olefir, A. I.; 1971.  Effect of chemical substances on the formation
  of acquired immunity.  Vrach. Delo 1971, 125-127. (Chem. Abstr. 75:
  107668z, 1971).
Olefir, A. I. and V. Kh. Vinogradova; 1968.  Embryotropic effect of the
  pesticides Sevin and Cyram.  Vrach. Delo 1968:103-106.  (Chem. Abstr.
  70:19205n, 1969).
Orlova, N. V.; 1970.  Adverse effect of Sevin on warm-blooded animals.
  Gig. Primen., Toksikol. Pestits. Klin. Otravlenii; No. 8:208-211.
  (Chem. Abstr. 77:122762k, 1972).
Orzel, R. A. and L. R. Weiss; 1966.  Effect of carbaryl (1-naphthyl
  /17-methylcarbamate) on blood glucose and liver and muscle glycogen in
  fasted and nonfasted rats.  Biochem. Pharmacol. 15:995-998.
Pekas, J. C.; 1971.  Intestinal metabolism and transport of naphthyl
  /V-methylcarbamate in vitro (rat).  Amer. J. Physiol. 220:2008-2012.
Pimentel, D.; 1971.  Ecological effects of pesticides on non-target
  species.  U.S. Gov't Printing Office #4106-0029.
Przezdziecki, Z. and W. Komorowska-Malewska; 1974.  Influence of car-
  baryl on Wistar rat gonads.  Mater. Nauk. Krajowego Zjazdu Endokry-
  nol. Pol. 8th 296-302. (Chem. Abstr. 83:23205y, 1975).
Robens, J. R.; 1969.  Teratologic studies of carbaryl, diazinon, norea,
  disulfiram, and thiram in small laboratory animals.  Toxicol. Appl.
  Pharmacol. 15:152-163.
Rogoff, M. H. and J. J. Reid; 1954.  Biological decomposition of 2,4-D.
  Bacteriol. Proc. (Soc. Am. Bacteriologists) 54:21.
Ryamushkin, G. and G. Yakub; 1971.  Content of Sevin in organs and
  tissue of mice, rabbits,  and chickens at different periods after
  poisoning.  Tr. Mold, Nauch.-Issled. Inst. Zhivotnovod.  Vet. 7:317-
  319.
Sanborn, J. R.; 1974.  The fate of select pesticides in the aquatic en-
  vironment.  EPA Ecological Research Series.  U.S. Gov't Printing Of-
  fice #5501-00995.
                                  557
-------
Sherman, M. and E.  Ross;  1961.   Acute and subacute toxicity of insec-
  ticides to chicks.  Toxicol.  and Appl.  Pharmacol.  3:521-533.
Shilova, S. A., A.  V. Denisova, E. L. Sedykh and K.  M.  Efron; 1973.
  Aftereffects of insecticide treatment in the subartics.   Zool. Zh.
  52:1008-1012. (Chem. Abstr. 80:23317z,  1974).
Shtenberg, A.  I. and M. V.  Ozhovan; 1971.  Effect of low Sevin doses
  on the reproductive function of animals in a number of generations.
  Vop. Pitan.  30:42-49. (Chem.  Abstr. 74:110889g, 1971).
Shtenberg, A.  I. and A. M.  Torchinskii; 1972.  Relations of general
  toxic, embryotoxic and teratogenic action of chemicals extraneous
  for the organism and the  possibilities  of predicting their influence
  on the antenatal period of ontogenesis.  Vestn. Akad. Med. Nauk SSSR
  27:39-46. (Chem.  Abstr. 77:44059v, 1972).
Shtenberg, A.  I., N. V. Orlova, A. L. Pozdnyakov, G. P. Toropova, E. P.
  Zhalbe, L. A. Khovaeva and M. Ya. Akincheva; 1970.  Functional and
  morphological parallels of the state of the gonads under the effect
  of Sevin.  Vop. Gig. Toksikol. Pestits., Tr. Nauch. Sess. Akad. Med.
  Nauk. SSSR 1967,  124-129. (Chem. Abstr. 74:98766e, 1971).
Shtenberg, A.  I., N. V. Orlova and A. M.  Torchinskii; 1973.  Action of
  pesticides of different chemical structure on the  gonads and embryo-
  genesis of experimental animals.  Gig.  Sanit. 1973:16-20. (Chem.
  Abstr. 80:594y, 1974).
Siebert, D. and G.  Eisenbrand;  1974.  Induction of mitotic gene con-
  version in Sacchavomyces  cerevi-S'iae by  77-nitrosated pesticides.
  Mutat. Res.  22:121-126.
Sikka, H. C.,  S. Miyazaki and R. S. Lynch; 1975.  Degradation of car-
  baryl and 1-naphthol by marine microorganisms.  Bull, Environ. Con-
  tarn. Toxicol. 13:666-672.
Singh, G.; 1974.  Degradation of insecticides by the cultured symbiotes
  of Cletus signatus walker (Coreidae, Heteroptera).  Curr. Sci. 43:
  624-625.
Smalley, H. E., J.  M. Curtis and F. L. Earl; 1968.  Teratogenic action
                                  558
-------
  of carbaryl in beagle dogs.  Toxicol. Appl. Pharmacol. 13:392-403.
Stadnyk, L., R. S. Campbell and B. T. Johnson; 1971.  Pesticide effect
  on growth and carbon-14 assimilation in a freshwater alga.  Bull.
  Environ. Contain. Toxicol. 6:1-8.
Stojanovic, B. J., M. V. Kennedy and F. L. Shuman; 1972a.  Edaphic as-
  pects of the disposal of unused pesticides, pesticide wastes and pes-
  ticide containers.  J. Environ. Qual. 1:54-62.
Stojanovic, B. J., F. Hutto, M. V. Kennedy and F. L. Shuman, Jr.;
  1972b.  Mild thermal degradation of pesticides.  J. Environ. Qual.
  1:397-401.
Stobwasser, I. H.; 1963.  Untersuchung der Riickstande einiger Phosphor-
  sSure ester und von Sevin in Mo'hren nach Freilandbehandlung.  Z.
  Pflanzenkrankh. Pflanzenschutz 70:459-464.
Sud, R. K., A. K. Sud and K. G. Gupta; 1972.  Degradation of Sevin (1-
  naphthyl W-methylcarbamate) by Aehromobacter species.  Arch. Mikro-
  biol. 87:353-358.
Tewfik, M. S. and Y. A. Hamdi; 1970.  Decomposition of Sevin by a soil
  bacterium.  Acta. Microbiol. Pol. Ser. B. 19:133-135. (Chem. Abstr.
  73:54953p, 1970).
Thompson, A. R.; 1970.  Effects of nine insecticides on the numbers and
  biomass of earthworms in pasture.  Bull. Environ. Contain. Toxicol.
  5:577-586.
Thompson, A. R. and W. W. Sans; 1974.  Effects of soil insecticides in
  southwestern Ontario on nontarget invertebrates:  Earthworms in pas-
  ture.  Environ. Entomol. 3:305-308.
Torchinskii, A. M.; 1974.  Significance of diets with different protein
  content in manifestations of teratogenesis and embryotoxic action of
  some pesticides.  Vop. Pitan. 1974:76-80. (Chem. Abstr. 81:115599s,
  1974).
Tos-Luty, S., W. Puchala-Matysek and J. Latuszynska; 1973.  Carbaryl
  toxicity in chick embryos. Bromatol. Chem. Toksykol. 6:409-411.
  (Chem. Abstr. 81:10296n, 1974).
                                  559
-------
Tos-Luty, S., E. Przylepa, J. Latuszynska and Z. Szukiewicz; 1974.
  Effect of carbaryl on the embryonic development of rats.  Bromatol.
  Chem. Toksykol. 7:57-62. (Chem. Abstr. 81:58998v, 1974),
Trifonova, T. K. , I. N. Gladenko, V. D., Shulyak; 1970.  Action of y-
  hexachlorocyclohexane and Sevin on the sex function.  Veterinariya
  (Moscow) 47:91-93. (Chem. Abstr. 73:119674v, 1970).
Tucker, B.V. 1973. tiux Insecticide.  Anal. Methods Pestic. Plant Growth
  Regul. 7:179-185.
Tucker, B. V. and D. E. Pack; 1972.  Bux Insecticide soil metabolism.
  J. Agr. Food Chem. 20:412-416.
Tucker, R. K. and D. G. Crabtree; 1970.  Handbook of toxicity of pes-
  ticides to wildlife.   U.S.  Fish and Wildlife Serv., Bur. Sport Fish
  Wildl. Resource Publ. #84.
Uchiyama, M., M. Takeda, T. Suzuki and K. Yoshikawa; 1975.  Mutageni-
  city of nitroso derivatives of W-methylcarbamate insecticides in
  microbial method.  Bull. Environ. Contain. Toxicol. 14:389-394.
Ukeles, R.; 1962.  Growth of pure cultures of marine phytoplankton in
  the presence of toxicants.   Appl. Microbiol. 10:532-537.
Urbanowicz, M., J. Gawecki and B. Bonk; 1973.  Effect of some carba-
  mate pesticides on the organism of the rat and in particular on the
  exocrine function of  the pancreatic gland.  Bromatol. Chem. Toksykol.
  6:413-418. (Chem. Abstr. 81:10297p, 1974).
Weil, C, S., M. D. Woodside,  C. P. Carpenter and H. F. Smyth, Jr;
  1972.  Current status of tests of carbaryl for reproductive and ter-
  atogenic effect.  Toxicol.  Appl. Pharmacol. 21:390-404.
Weil, C. S., M. D. Woodside,  J. B. Bernard, N. I. Condra, J. M. King
  and C. P. Carpenter;  1973.   Comparative effect of carbaryl on rat
  reproduction and guinea pig teratology when fed either in the diet
  or by stomach intubation.  Toxicol. Appl. Pharmacol,, 26:621-638.
Whitehurst, W.  E. , E. T., Bishop and F. E. Critchfield; 1963.  The meta-
  bolism of Sevin in dairy cows.  J. Agr. Food Chem. 11:167-169.
                                  560
-------
Wuu, K. D. and W. F. Grant; 1966.  Morphological and somatic chromo-
  somal aberrations induced by pesticides in barley (Hordeum vulgare).
  Can. J. Genet. Cytol. 8:481-501.
Yakim, V. S.; 1967.  Data for substantiating the maximum permissable
  concentration of Sevin in the air.  Gig. Sanit. 32:29-33.
Yu, C., G. M. Booth, D. J. Hansen and J. R. Larsen; 1974.  Fate of Bux
  insecticide in a model ecosystem.  Environ. Entomol. 3:975-977.
Zabezhinskii, M. A.; 1970.  Possible carcinogenic effect of 3-Sevin.
  Vop. Onkol. 16:106-107. (Chem. Abstr. 75:32870y, 1971).
Zhavoronkov, N. I., A. V. Akulov, S. D. Antsiferov, A. P. Verkhovskii
  and S. M. Evdokimov; 1973.  Effect of carbamates on hens.  Veteri-
  nariya  (Moscow) 114-116.  (Chem. Abstr. 79:122422r, 1973).
Zinchenko, V. A. and T. V. Osinskaya; 1969.  Change in the biological
  activity of soil during composting with herbicides.   Agrokhimiya
  1969:94-101. (Chem. Abstr. 72:2381k, 1970).
                                 561
-------
                               SECTION V
                        FUNGICIDES AND FUMIGANTS
Captan
Captan is the common name for 3a,4,7,7a-tetrahydro-2-(trichloromethyl)
thio-lH-isoindole, a fungicide used mainly for foliage protection which
was introduced by Standard Oil in 1949 under the name Orthocide.  Cap-
tan forms white crystals with a melting point of 178 C and a vapor pres-
sure of less than 0.01 mm at 25 C.  It is insoluble in petroleum oils,
and its water solubility at room temperature is less than 0.5 ppm.  It
is soluble in xylene, chloroform, acetone, and isopropanol, and stable
except under alkaline conditions.
Captan is produced by the reaction of trichloromethylsulphenyl chloride
on tetrahydrophthalimide.  The technical product is 93 to 95 percent
pure captan and forms an amorphous yellow solid with a pungent odor.
The melting point of technical captan is between 160  and 170 C.  It
is formulated as 50 percent or 83 percent wettable powders, 5 percent
dust, or as a 75 percent dust for seed treatment.
Degradation-
Biological—When 840 million Neurospora crassa spores were incubated
with 375 yg captan, degradation of captan to carbonyl chloride occur-
red in 20 minutes, with no formation of carbon disulfide (Somers et al.
1967, Richmond and Pickard 1967).  Cell thiols were implicated in the
                            35
degradation and most of the   S was eventually bound to oxidized gluta-
thione and its derivatives (Richmond and Somers 1968).  Captan lost 50
percent of its bioactivity against Khizoctonia solani after three weeks'
incubation in humus-sandy forest soil  (Kluge 1969a).
         14                                              14
Rats fed   C-labeled captan excreted 51.8 percent of the   C in their
urine as thiazolidine-2-thione-4-carboxylic acid, a salt of dithiobis
(methane sulfonic acid) and the disulfide monoxide of dithiobis(methane
sulfonic acid).  Radioactive C0_ was exhaled, accounting for almost 23
percent of the label, and 15.9 percent of the label was eliminated in
                                   562
-------
the feces.  Less than one percent of the label remained in the tissues
(DeBaun et al. 1974).  Gastro-intestinal degradation was highly signi-
ficant, since in rats which were injected intraperitoneally with cap-
tan, 50 percent of the radioactive label was excreted in nine days, but
administered orally the label from captan was 50 percent excreted with-
in two hours (DeBaun et al. 1974).
     35
When   S-labeled captan was fed to rats, 90 percent of the label was
eliminated in 24 hours (Seidler et_ al. 1971).
Chemical and physical—Captanrdecomposes between 200 C and 245 C leading
to a 52 percent weight loss and formation of hexachlorodimethyl disul-
fide and tetrahydrophthalimide (Pfeifer and Pfeifer 1970).  Captan de-
gradation in soil was not affected by changes in pH between 3.6 and 7.4
(Kluge 1969b).
                       «
Transport-
When the mobility of several fungicides was examined in soil columns
with several types of soil, all were more mobile in sandy loam than in
loam, and in dry than wet soil.  Peat moss greatly inhibited the mobi-
lity of all compounds.  In general, suspended compounds were less mo-
bile than dissolved compounds.  Captan as particles of 14.5 y was less
mobile than when particles of 1.05 y were used (Munnecke 1961).
Persistence-
Captan was found to be degraded rapidly in most soils.  Bioassay with
Myvofheoi-um ve?'Pueca"La indicated a 50 percent loss of activity after
seven days in sandy soil, three to four days in moist soil, and less
than one day in compost soil.  Under conditions of high local concen-
trations, much longer persistence was noted (Griffith and Matthews
1969).  Agnihotri (1970, 1971) and Burchfield (1959) also found that
captan was persistent for less than one week in moist soil.
In sharp contrast, Munnecke (1958) found persistence of diffusible ac-
tivity for 65 days after captan was applied to a mix of sand and peat
                                   563
-------
while under the same conditions nabam was inactivated within hours.   If
the mix was first sterilized, captan persisted for up to 150 days.  Ag-
nihotri (1970), observing that Munnecke's data were atypical, suggested
that the acidity of the peat moss was unfavorable for growth of captan-
degrading bacteria.  The amount of organic matter, rather than clay,  in
the soil determines the rate of captan release (Rersheim and Linn 1968).
Fifty percent of the applied captan persisted for less than one hour  in
water at 25 C, but for seven hours at 12 C (Hermanutz e_t_ al_. 1973).
These data suggest that biodegradation of captan is rather rapid, which
explains the nonpersistence of captan under field conditions.  No data
on the degradation products of captan or their persistence in soil were
available.
Effects on Soil Microorganisms-
As would be expected of a fungicide, captan sharply inhibited nontarget
fungal growth in many studies (Wainwright and Pugh 1974, Naumann 1970,
Domsch 1959) but after 28 days fungal populations had increased above
pretreatment levels even if twice the usual agricultural levels of cap-
tan were used.  Glioo1adiwn3 Penioil1ium3 and Tviohoderma predominated
(Wainwright and Pugh 1974).  A decrease in fungal diversity was obser-
ved by Naumann (1970).  When captan was applied to forest soil at 62.5,
125, and 250 ppm, three pathogenic fungi were destroyed (Rhizoatoniaf
Pythium), three saprophytic fungi were stimulated (Peni-Q-111-ium, Tricho-
derma, Fusapiim) and actinomycetes and bacteria were stimulated for up
to five weeks (Agnihotri 1970, 1971).  In laboratory cultures, agricul-
tural levels of captan inhibited four microfungi (Hansenula, sattamus,
MUOOT hi-emal'is, Penni-ai-lli-um stipitatwr and Trichoderma vir"ide) from
cattail marsh, but in the field no effects on these fungi were observed
(Tews 1971).
Soeder et_ aK (1969) found captan almost as toxic to some algae as to
Neupospora avassa:  37 or 40 ChloTella species were strongly inhibited
                                   564
-------
by as little as five rag/liter  (five ppm) captan in shake solution where-
as Seenedesmus species were relatively resistant even at 50 rag/liter
(50 ppm) of captan.  With respect to nontarget microorganisms and soil
processes, captan generally stimulated ammonification and  inhibited ni-
trification, while bacterial growth was sometimes stimulated and some-
times inhibited.  These data are summarized in Tables 85 and 86.
In addition to the considerable direct toxicity which it exerts on some
microorganisms, captan induces DNA base changes (Kada et_ al_. 1974).   It
is mutagenic in the bacteria Esohevlohla ooll (Legator et_  al^. 1969,
Clark 1971, Bridges et al. 1972, 1973) and Salmonella (Seiler 1973),  in
the fungus Altevnarla mall (Slifkin 1973), and induces mitotic gene con-
version in the yeast Saodhapomyoes cerewis'iae (Siebert et  al. 1970).
In the host-mediated assay in mice, captan was mutagenic in two species
of Salmonella (Buselmaier et al. 1972).
In summary, it is apparent that captan strongly affects soil microorgan-
isms and soil processes and must be expected to alter the  soil complex
profoundly whenever it is applied to soil, even if the precise changes
cannot be predicted.
Effect on Non-Target Species-
Invertebrates—Captan is essentially nontoxic to insects under ordinary
usage (Pimentel 1971, Beran and Neururer 1956).
Plants—Captan was reported to stimulate plant growth (Kittleson 1963),
but 1,000 ppm inhibited root growth of corn seedlings (Dugger et al.
1958).  Levels of 100 and 200 ppm of a 50 percent wettable powder de-
creased corn growth but stimulated growth of bean plants in soil con-
sisting of silty clay loam, peat and fine sand in a 3:1:1  ratio (Cole
et^al. 1968).
Fish—Ninety percent of zebrafish larvae exposed to one ppm of captan
died within 90 minutes (Abedi and McKinley 1967).  Lethal  concentrations
were reported to be 29 ppm for brook trout (Salvellnus fontlnalls~), 64
                                  565
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ppm for fathead minnows (Pimephales promelas"), and 72 ppm for bluegills
(Lepomia macro shims') and the breakdown products of captan were not  tox-
ic (Hermanutz et_ al. 1973).
Birds—Captan is relatively nontoxic in birds with a five-day LC,... of
2,000 ppm in bobwhite and over 5,000 ppm in mallards, pheasants, and
coturnix quail (Pimentel 1971).  If captan is injected into hens' eggs
it causes leg and wing malformations as well as significant mortality
(Verrett et al. 1969).
Mammals—The acute oral LD -. of captan is more than 8,000 mg/kg in rats
(Jones et al. 1968), but 250 mg/kg caused poisoning in sheep  (Palmer
and Radeleef 1964).  Chronic feeding of 0.05 to 0.4 ppm for six months
did not affect two cows or five swine so fed (Johnson 1954), while 140
days feeding with corn contaminated by 67 g/bushel apparently increased
weight gain in steers (Dowe et^ aJ^. 1957).  In contrast, Grabarska (1972)
reported serious dystrophic changes in many organs when rabbits were
given 500 mg/kg for 14 days and similar damage was reported by Vasha-
kidze et^ al.. (1973) when 265 mg/kg were given to rats for two months, or
20 to 55 mg/kg were given for twelve months.  Treatment with 100 mg/kg/
day of captan decreased the level of hepatic respiratory enzymes in
guinea pigs (Krolikowska-Prasal 1973) .
Since captan was observed to denature calf thymus in vi't-TO and cause al-
kylations i/n vivo in mice it was considered carcinogenic by Anderson and
Rosenkranz  (1974).  The teratogenicity of captan is theoretically at-
tractive because it shares the phthalimide moiety with thalidomide but
the data are inconclusive (Kennedy et_ aL_. 1968, 1975; Vondruska et al.
1971, Shea 1972).  Even in the absence of teratogenicity, however, con-
siderable embryotoxicity is often observed (Kennedy £jt al. 1975) .  The
data on the long-term effects of captan and related fungicides have
been critically reviewed by Bridges (1975) who concluded that captan
was mutagenic in rats and bacteria, was teratogenic, and had been in-
sufficiently tested for carcinogenesis.
                                  568
-------
Conclusions-
Captan is eminently suited to soil degradation if well dispersed, rather
than massed, in the soil, but since captan is a microbial mutagen no
form of unmonitored soil disposal can be recommended.  The low persis-
tence of captan in water makes degradation in lagoons a possibility,
subject always to the oaveat of mutagenesis.  There are no data avail-
able on the feasibility of chemical or thermal destruction of captan,
so no conclusions as to the relative merits of different modes of dis-
posal are possible.
                                  569
-------
Dodine
Dodine is the common name for dodecylguanidine acetate, referred to as
doquadine and taitrex in France and in the USSR, respectively, and in-
troduced by American Cyanamid as Cyprex or Melprex in 1957.  Dodine is
a white crystalline solid with a melting point of 136°C, soluble in
water and ethanol, and insoluble in most organic solvents.  The free
base is liberated by strong alkalies, but the acetate salt is stable
in moderately alkaline as well as moderately acid solutions.  Dodine
is used chiefly as a foliar fungicide, particularly against apple or
pear scab and cherry leaf spot.  The usual formulations are 65 per-
cent and 80 percent wettable powders, 75 percent dusts, or 20 percent
liquid.
                                                              *
Degradation-
                                          *
The major degradation product of dodine in plants is creatine (Kaufman
                                                                •
1974).  Dodine was adsorbed to the same extent by dead as by viable
fungal spores; its rapid adsorption and Langmuir-type isotherm sugges-
ted ionic bonding to Alternavia tenuis spores, while the relative ir-
reversability of its adsorption to Neiipospora CTassa spores suggested
covalent bonding.  The presence of calcium, magnesium, or uranil salts
decreased dodine bonding to fungal spores (Somers and Pring 1966).
Goldberg and Wershaw (1965) found Aahromobacter and Flavobacterium
species could grow with dodine as the sole source of carbon.  When river
mud from the Denver area was treated with dodine, five percent of the
fungicide was degraded in 68 days whether or not the mud was precondi-
tioned (Goldberg and Wershaw 1965).  There was no information on the
chemical, physical or photolytic degradation of dodine.
                                   570
-------
Transport-
There were no data available on the mobility of dodine in soil, water
or air.
Persistence-
There was no data available on the persistence of dodine in soil.
Effects on Non-Target Species-
Dodine was not observed to induce mitotic gene conversion in the yeast
Sacahapomyces cepevis'iae under conditions which resulted in gene con-
version by both captan and folpet (Siebert j2t al_. 1970).
Shaw (1959) found no difference in honey bee mortality between control
and dodine-treated fields.  Some reduction in mirid predators was
found when dodine was applied to orchards, but 500 ppm dodine in water
did not affect adult female parasitic wasps (TvidhogTcctnma) after a 24-
hour exposure (Pimentel 1971).
No data on the effects of dodine on birds, amphibians, fish, or soil
fauna were available.  The acute oral LD   of dodine was determined to
be 566 mg/kg in rats by Jones et_ al_. (1968), and 1,000 mg/kg by Levin-
skas et al. (1961).  The latter calculated a 24 hour dermal LD... of
     	                                                    DU
2,000 mg/kg in rabbits.  Chronic feeding of dodine to rats resulted in
a reduction in the weight gain of rats fed 3,200 ppm for 100 days or
800 ppm for 2 years, but no effects on reproduction were observed after
feeding 800 ppm for 2 years.  In dogs, levels of 200 or 800 ppm fed
for one year resulted in slight thyroid stimulation.  No increase in
pituitary chromatophobe adenomas was seen (Levinskas et al. 1961).
Conclusions-
Since no data were available on the persistence of dodine, its nonbio-
logical degradation, or its transport in soil or water, no conclusions
can be reliably drawn.  The relatively low mammalian toxicity of dodine
                                  571
-------
is reassuring, but its status as a fungicide militates against soil
disposal in the absence of information about its toxicity to, and degra-
dation by, soil organisms.
                                   572
-------
Maneb, Nabam, and Zineb
Maneb is the common name for l,2-ethanediylbis(carbamodithioato)
(2)-manganese, a protective foliar fungicide which was introduced in
1950 by E. I. du Pont de Nemours and Co. as Manzate and by Rohm and
Haas as Dithane M-22.  Pure maneb is a yellow crystalline solid which
decomposes before melting, is slightly soluble in water and insoluble
in most organic solvents.  Maneb is synthesized by reacting a water-
soluble ethylenebis-dithiocarbamate with either manganous sulphate or
manganous chloride.  The technical product is a light-colored solid.
Exposure to either moisture or acids results in decomposition, with for-
mation of polymeric ethylenethiuram monosulfide.  Maneb is formulated as
a 70 percent wettable powder or in sprays which contain 1.5 to two Ibs.
per gallon.
Nabam, the common name for 1,2-ethanediylbis-carbamodithioic acid-disodium
salt, was introduced in 1943 by E. I. du Pont de Nemours and Co. as
Parzate, and by Rohm and Haas as Dithane D-14.  It is synthesized by the
interaction of ethylenediamine and carbon disulfide in the presence of
sodium hydroxide.  It forms colorless crystals of the hexahydrate which
are soluble in water to about 20 percent (expressed as the anhydrous salt)
at room temperature, forming a yellow solution.  Because the crystalline
form is unstable, nabam is formulated as a 19 percent aqueous solution.
Use of two quarts of this solution to one pound ZnSO. permits conversion
to zineb.
Zineb is the common name for l,2-ethanediylbis(carbamodithioato)
(2)-zinc, was introduced in 1943 as an improvement on nabam and marketed
as Dithane Z-78 by Rohm and Haas, and as Parzate-Zineb by E. I. du Pont
de Nemours and Co.  Zineb is a light-colored powder made by precipitating
nabam with soluble zinc salts.  It decomposes before melting, has a
                                   573
-------
negligible vapor pressure at room temperature and an aqueous solubility
of about 10 ppm at 20 C.  It is soluble in pyridine and is somewhat
unstable to light, heat, and moisture.  The polymer produced by precip-
itating zineb from concentrated solution has a lower fungicidal activity.
Zineb is usually formulated as a 65 percent wettable powder.
Degradation-
Few data on microbial degradation of the dithiocarbamate fungicides ex-
ist, in part because of their rapid decomposition in the presence of
moisture.  Asperg-illus niger degraded maneb more readily than zineb;
almost no water-soluble compounds of the latter were observed (Engst
and Schnaak 1967).  Figure 18 shows the degradative pathways of the
dithiocarbamate fungicides.  Essentially identical degradation products
are found for all three compounds:  ethylenebisthiuram disulfide, ethyl-
enebisthiourea, ethylene diisothiocyanate, CS0, and H0S.  Munnecke et al.
                                             z       z             	
(1962) did not find H^S when nabam was degraded although Klisenko and
Vekshtein (1971) reported elemental sulfur.  Engst and Schnaak (1970)
included ethylenediamine and elemental sulfur among degradation pro-
ducts; the former was reportedly the major fungitoxic product of nabam
                                           14
(Cox et^ a.1^. 1951).  In rats, 55 percent of   C-maneb was excreted as
ethylenediamine, ethylene bisthiuram monosulfide and ethylenethiourea
(Seidler £t al. 1970).
In the laboratory, zineb lost its efficacy in 16 days at 30  or 40 C.
In the field, the fungitoxicity of zineb increased for four days, then
declined with 50 percent of its bioactivity gone after 16 days (Grandi
^ al. 1958).  It is noteworthy that the degradative products of the
dithiocarbamates are probably the active fungicides.  Rich and Horsfall
(1950) observed that SO-, H-S, and ethylene thiourea accounted for only
part of the fungitoxicity of nabam; Engst and Schnaak (1967) considered
ethylenethiuram monosulfide to be the chief fungitoxin of the dithio-
carbamate fungicides.  Engst (1970) noted the greater toxicity of some
metabolites of these fungicides, and cited ethylenebis(thiouronium sul-
                                   574
-------
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                                 575
-------
fide) as the major fungitoxin.  Viel and Chancogne (1966) tentatively
identified the fungicidally active product of maneb as ethylenethiuram
monosulfide.
Zineb was more rapidly degraded in soil than in liquid cultures.  Ex-
posure to sunlight for 19 months did not effect its degradation (Iley
and Fiskell 1963).  Zineb was decomposed by temperatures of 200 C, with
a weight loss of 34 percent and a change in color to brownish-black
(Stojanovic et_ a^. 1972b) .  At 900 C, the volatile products of zineb
decomposition were CO, CO , H S, and NH  (Kennedy e_t al. 1972b) .
Chemically zineb could be degraded 99 percent or more by treatment with
liquid NH,, plus metallic sodium or lithium, or with sodium biphenyl,
while triethanolamine was not effective.  Treatment with 18/17 H_SO. re-
                                                              2  4
suited in formation of H^S and free zinc (Kennedy e_t_ al_. 1972a).  Nabam
in soil was inactivated nonbiologically and very rapidly (Munnecke 1958).
Transport-
In soil columns, mobility was more affected by soil type for fungicides
in suspension, such as zineb, than for those in solution, such as nabam.
Dissolved fungicides were more mobile than suspended fungicides, and
mobility of all fungicides was enhanced in wet rather than dry soil and
in sandier and/or more porous soil.  Peat moss greatly decreased mobi-
lity (Munnecke 1961).  No data were available on the transport of maneb,
nabam, or zineb into or within water.  Ethylenethiourea was taken up by
cucumbers (Vonk 1971).
Persistence-
As suggested by the ready decomposition of the dithiocarbamates by mois-
ture, persistence in soil appears to be low.  Maneb persisted for three
weeks when applied at one ppm, and more than 11 weeks but less than 12
weeks when applied at 1,000 ppm (Chinn 1973).  No data were available
on the persistence of the intermediate degradation products of the di-
thiocarbamate fungicides in soil.  When beans and tomatos were treated
                                   576
-------
at seven day intervals with maneb with seven and eight treatments re-
spectively, residues were present on the plants 14 days later  (Newsome
et_a±. 1975).
Effects on Soil and Soil Organisms-
The effects of maneb, nabam, and zineb on soil processes and soil micro-
organisms are summarized in Tables 87, 88 and 89.  It can be seen that,
despite their economic status as fungicides, the dithiocarbamates are
not uniformly or universally toxic to soil organisms.  Even relatively
rapid recovery of fungal numbers (within 60 days) has been reported
(Chandra and Bollen 1961) but after nabam treatment, soil fungal popu-
lations consisted mostly of Tr-ichoderma and Penio-illvum (Corden and
Young 1965).
Dubey and Rodriguez (1970) analyzed the effects of nabam on nitrifica-
tion and ammonification and found that nitrification was less  inhibited
in rapidly nitrifying loam soil than in slowly nitrifying lateritic
soil.  The ammonia-oxidizing bacteria were most strongly affected,
while nitrite-oxidizing bacteria were not inhibited.  Maneb at 15 or 60
ppm inhibited nitrification for eight weeks, while ammonification was
inhibited only at 960 ppm.  Zineb applied to calcareous loam (pH 7.5)
at 5,000 ppm reduced CO, evolution by 86 percent over a 56 day observa-
tion period (Stojanovic et al. 1972a).  Mutagenesis was reported in
Alternavia mali- by maneb, nabam and zineb (Slifkin 1973), and  in Sal-
monella by maneb (Seiler 1973) but maneb was reportedly not mutagenic
in Saccharomyces (Siebert et^ al. 1970).
Effects on Non-Target Species-
No evidence of mutagenesis by zineb was found in two studies on Droso-
plntla melanogaster (Pilinskaya 1967, Ryazanov 1967).  Zineb was essen-
tially nontoxic to honeybees at even the highest agricultural  levels
of exposure (Nazarov 1966).
                                   577
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In the amphibian Xenopus 1aevis3 nabam and maneb affected growth, mel-
anogenesis, and notochordal development when eggs were exposed to 1-5
ppm for 36-38 hours before hatching  (Bancroft and Prahlad 1973, Prahlad
et al. 1974).  In hens, treatment with one percent of the LD^ of zineb
— ~—~                                                       _)u
decreased fertility, impaired egg development and caused degenerative
changes in hens' livers, kidneys, and reproductive organs (Zhavoronkov
et_ al. 1973).
The oral LD,-n of dithiocarbamate fungicides to rats was calculated  to
be between 1,000 and 8,000 mg/kg (Jones et_ a^. 1968).  Inhalation of
zineb was observed to cause liver and kidney damage in albino rats
(Ivanaova 1966).  A single dose of not more than 500 mg/kg or ten doses
of 100 to 250 mg/kg of zineb did not cause poisoning in sheep (Palmer
and Radeleef 1964).  Nabam pretreatment decreased the acute toxicity
of methyl parathion in mice (Lange et_ al^. 1975).  Maneb and zineb,  if
given at 250 mg/kg/day, reportedly increased blood coagulability in
rabbits (Karpenko 1975).
In cell culture, the carbamates zineb and carbaryl were found to accum-
ulate more readily than the organochlorines HCH and DDT with lethal
levels markedly lower in culture than in vivo (Shpirt 1973).  Zineb was
considered to affect cell mitotic activity and cause chromosome damage
(Rashev 1972); similar results were obtained when mice were injected
with maneb or zineb (Kurinnyi and Kondratenko 1972) .
Ethylene thiourea is a known thyroid carcinogen (Bontoyn and Looker
1973, Hylin 1973) and it also caused lung tumors in rats (Rappoport et
al. 1966) or orally (Didenko and Gupalovich 1975, Chernov and Khitsenko
1969, Chernov 1972, Andrianova adn Alekseev 1970, Engst and Schnaak
1974).  Maneb caused lung adenomas in mice (Chernov 1972) and in rats
(Balin 1970).  Chepinoga et^ aJU (1970) administered 0.17 times the  LD--
of zineb to rats, and classified the compound as blastemogenic and  em-
bryotoxic while in the same study, maneb was found to be strongly em-
bryotoxic and weakly mutagenic.  Zineb was not mutagenic and maneb  was
                                  581
-------
not tested for carcinogenicity.  Zineb was a transplacental carcinogen
in mice (Kuitnitskaya and Kolesnichenko 1971).
Ethylene thiourea, a degradation product of the thiocarbamate fungi-
cides, was teratogenic and embryocidal in rats but only embryocidal in
rabbits (Khera 1973).  Maneb was embryocidal in rats, and also caused
reversible sterility of both males and females (Martsori 1969).  Maneb
and zineb were teratogenic in rats only at levels greater than 2 g/kg,
leading Petrova-Vergieva and Ivanova-Chemishanska (1971, 1973) to con-
clude that human teratogenesis was unlikely.
Conclusions-
All methods of disposing of the dithiocarbamate fungicides maneb, nabam
and zineb must take into account the carcinogenic metabolite ethylene
thiourea.  If and only if this compound can be shown to be non-persis-
tent in soil is soil disposal of these compounds feasible.  Either che-
mical or thermal decomposition requires caution bacause of the release
of H,jS, NH , and/or CO, but both are feasible for the dithiocarbamate
fungicides.
                                  582
-------
Methyl Bromide
Methyl bromide is the common name for bromomethane, a colorless gas
with a boiling point of 4.5 C and a freezing point of -93 C.  The
colorless liquid has an odor similar to that of chloroform.  Its solu-
bility in water at 25 C is 13,400 ppm and it forms a voluminous crystal-
line hydrate with ice water.  It is stable, neither corrosive nor in-
flammable, and soluble in most organic solvents.  Methyl bromide is
synthesized by the action of hydrobromic acid on methanol.  In the
United States it is produced by American Potash, Dow Chemical Co.,
Frontier Chemical Co., Great Lakes Chemical Co. and Michigan Chemical
Co. for use as a soil fumigant against nematodes, fungi, and weeds.
It is also used in the fumigation of storage areas and of stored pro-
ducts.
Degradation-
Methyl bromide is decomposed by oxidative processes in soil and/or con-
jugated with sulfhydryl-containing compounds, with concomitant debrom-
ination (Goring et al. 1975) .  Shiroishi and co-workers (1964) used
14
  C-methyl bromide to fumigate soil and found the residual radioacti-
vity after one month to be heavily associated (44 percent) with pro-
tein.  The same study demonstrated conjugation of methyl bromide with
free amino acids.
In the absence of oxygen, methyl bromide heated to 550 C decomposed to
form methane (20 percent), hydrogen bromide (45 percent), considerable
quantities of hydrogen, bromine, bromoethane, and CFL.  Other products
included (CH Br) , anthracene and pyrene (Chaigneau et al. 1966).
            /   2.                                   	 	
Photolysis of methyl bromide produced CH, when carried out in the pre-
sence of silver, copper, or gold at temperatures between 50  and 250 C.
Some C?Hfi was also recovered (McTigue and Buchanan 1959).  Photolysis
                                  583
-------
of methyl bromide at 1,850 A at 25 to 30 C in the presence of three
percent bromine resulted in formation of methane (Kobrinsky and Martin
1968).
Transport-
Methyl bromide is primarily lost into the air after soil fumigation.
Some adsorbed methyl bromide might move with or through soil, but no
                                                 3
data were available.  Soil fumigation with 73 g/m  of methyl bromide
resulted in residues of up to 45 ppm in mature tomatoes, although the
usual residues were considerable lower (Kempton and Maw 1973) .   Stored
beans retained very high levels of methyl bromide for more than 17 days
after treatment (Seefeld and Beitz 1968).  Aged methyl bromide was less
readily taken up by plants than fresh, and plants accumulated more
methyl bromide in roots and fruit than in leaves or stalks (Malkomes
1972).
Persistence-
Methyl bromide is considered a nonpersistent pesticide inasmuch as more
than 50 percent disappears from soil within one-half month (Goring et
al. 1975).  Sorption of methyl bromide was greatest in peat, least in
sand, and intermediate in clay soils; all soils adsorbed more methyl
bromide when dry.  Moisture did not, however, increase the loss of
methyl bromide from empty chambers (Chisholm and Koblitsky 1943) .  In
sandy clay soil, eleven percent moisture affected little reduction of
methyl bromide in a one-hour period (Fuhr et_ al. 1948).  The depth of
soil penetration by methyl bromide depended on the dose applied (Mal-
komes 1972).  Food residues of methyl bromide decreased with decreasing
temperatures during fumigation (Dumas 1973) .
Effects on Non-Target Species-
The toxicity of methyl bromide to soil organisms can be gauged by its
use as an herbicide, fungicide and nematocide (Martin 1968).  Essen-
tially complete extermination of soil fauna in pine litter followed
                                   584
-------
                     2
treatment with 25 g/m   (250.4 kg/ha) of methyl bromide  (Heungens 1972),
Among bacteria, spore forming organisms were more resistant than ni-
trifying bacteria and fungi were more sensitive than actinomycetes.
Methyl bromide was both less toxic and less selective in its toxicity
than chloropicrin (Reber 1967).  Toxicity was greater in wet than in
dry soils (McClellan et_ al. 1974) .
                                             2
In fine sand or fine loamy sand, 2 lbs/100 ft  (978 kg/ha) of methyl
bromide decreased nitrification for 50 days, but overall bacterial
activity increased above pretreatment levels after three weeks, and
numbers of TT-ichoderma exceeded pretreatment levels after 30 weeks
(Overman 1972) .  Winfree and Cox (1958) observed a two-month inhibi-
tion of soil nitrification in Everglades peat after treatment with
                              2
methyl bromide at 2 lbs/100 ft  (978 kg/ha).
Jenkinson and Powlson (1970) were able to detect effects of the elimi-
nation of a section of the soil biomass by methyl bromide years later
by stressing the soil organisms with formalin or radiation.  Second
and subsequent fumigation resulted in less nitrogen mineralization re-
gardless of the populations of pathogens present.  These data suggest
permanent effects of methyl bromide on the complex of soil microorgan-
isms even after the ordinary parameters of soil effects have returned
to normal.
In the host-mediated assay in mice, methyl bromide was mutagenic for
Salmonella typh-imurium and Salmonella marcesoans (Buselmaier et_ al.
1972).
Conclusions-
As a gas, methyl bromide would be totally unsuitable for soil disposal
even if its toxicity to soil microorganisms were less profound or less
long-lasting.  A reasonable method cf disposal is suggested by the
ready anoxic decomposition of methyl bromide at 550 C.
                                  585
-------
Pentachlorophenol
Pentachlorophenol is a white crystalline solid which is only slightly
soluble in water (20 ppm at 30 C) but soluble in most organic solvents.
It has a melting point of 190°C and a boiling point of 293°C, its va-
por pressure increases from 0.00011 mm Hg at 20 C to 0.12 mm Hg at
100 C, and it is volatile in steam.  Technical pentachlorophenol is a
dark grey powder with a melting point between 187 and 189 C.
Pentachlorophenol was introduced as a wood preservative in 1936 and is
used as a fungicide, herbicide, defoliant and insecticide.  The sodium
salt of pentachlorophenol is readily water soluble (300,000 ppm water
at 25 C), but insoluble in petroleum oils.  It is used as a mollusci-
cide and in other situations requiring aqueous solutions.  Pentachlor-
ophenyl laurate, a nonfungicidal analog of pentachlorophenol, has been
used as a mothproofing compound (Adema et_ al. 1967).
Pentachlorophenol, produced by the catalytic chlorination of phenol,
is manufactured by Dow Chemical Co. as Dowicide 7 and by Monsanto
Chemical Co. as Santophen 20.  The corresponding sodium pentachloro-
phenate products are Dowicide G and Santobrite.  The technical product
is used directly or is formulated in oil.  Although pentachlorophenol
is not deemed to need a trivial name, it is frequently referred to as
PGP.
Degradation-
Biological—Pentachlorophenyl laurate was hydrolyzed to pentachlorophe-
nol in the presence of soil, presumably by microbial action  (Allsopp
et_ al. 1970) .  Degradation of pentachlorophenol by Tvic'hoderma virga-
twn was observed, but no metabolites were identified (Cserjesi 1967a) .
A single strain of Aphaloaseus fragrans was acclimatized to 0.2 per-
cent (2,000 ppm) pentachlorophenol; all other species tested (Tvioho-
                                  586
-------
derma hapz-ianwrn, Tyiehoderma virgatum^ Tp-Lohoderma wirid-i3  Ceratoays-
tis pil-ifeva3 Chaetom-ium globosum3 Graphium sp., Penieilliim  sp.) were
inhibited by 0.04 percent  (400 ppm) pentachlorophenol  (Cserjesi  1967b) .
Lyr (1963) reported detoxification of chlorinated phenols by  fungal
oxidases, but no ring cleavage occurred, and the more  highly  chlorina-
ted compounds were less susceptible even to detoxification.   In  paddy
soil, pentachlorophenol decomposed to mono-, di-, tri-, and tetrachlor-
ophenol.  Decomposition was more rapid in mature paddy soil than in
immature soil with higher  levels of volcanic ash.  Since soil sterili-
zation inhibited decomposition, microbial action was presumed (Ide et
al. 1972).
Suzuki and Nose (1970) analyzed decomposition of pentachlorophenol in
farm soils, and observed that 90 percent was detoxified in  ten days
when 100 ppm were applied  to the soil, but only ten percent detoxifi-
cation of 1,000 ppm occurred in the same period.  Chloropicrin
and C-H.HgO-acetate enhanced detoxification, whereas captan was inhi-
     o b
bitory.  A gram-positive bacillus converted PCP to pentachloroanisole,
with hydroquinone dimethyl ether as a minor product  (Suzuki and Nose
1971) .  Chu and Kirsch  (1972) reported that a species of saprophytic
coryneform bacteria was able to grow using pentachlorophenol as the
sole source of carbon.  No other reports of ring cleavage were found.
Vel-Muzquiz and Kaspar  (1974) considered microbial degradation to be
relatively insignificant in the detoxification of pentachlorophenol,
since they could not find evidence that microorganisms could grow with
PCP as the sole source of carbon.
Chicken-house litter treated with pentachlorophenol  imparted a musty
taint to the chicken meat due to the microbial conversion of PCP to
2,3,4,6-tetrachloroanisole (Curtis et^ a^. 1972).  In rats and mice,
tetrachlorohydroquinone was the major, if not only, metabolite (Jakob-
sen and Yllner 1971, Ahlborg and Lindgren 1974).
                                  587
-------
Photolytic—Sodium pentachlorophenate was inactivated by light of less
than 330 nm when tested by bioassay against snail eggs (Hiatt et al.
1960).  Pentachlorophenol itself was, in contrast, very stable to light
(Crosby and Hamadmad 1971).  Among numerous compounds, including oxi-
dized monomers and dimers, produced by the action of light on sodium
pentachlorophenate were five products with greater toxicity to fish.
Chloranilic acid was also produced, lending a purple color to the so-
lution (Munakata and Kuwahara 1969).  Under field conditions, sodium
pentachlorophenate was more rapidly degraded in clear, shallow water
than in deep, turbid water, (Bevenue and Beckman 1969) suggesting that
photolysis is a major degradative route.
When sodium pentachlorophenate was exposed to sunlight, traces of oc-
tachlorodibenzo-p-dioxin and other unidentified dioxins were found.
The latter were unstable, but octachlorodibenzo-p-dioxin was stable to
ultraviolet (Stehl et_ al. 1973, Plimmer 1973).
In the presence of a large excess of oxygen, pentachlorophenol exposed
to UV light of 230 nm or 290 nm was decomposed with 69 mg of the ini-
tial 80 mg remaining after seven days.  In addition, 15 mg CO  and six
mg HC1 were also recovered (Gaeb et al. 1975) .
Chemical and physical—Pyrolysis of PCP at 300 C for 24 hours resulted
in conversion to hexachlorobenzene, octachlorodiphenylene dioxide and
other neutral polymeric products (Sanderman e_t_ al^. 1957).  Slow pyro-
lysis at 200 C resulted in production of octachlorodibenzodioxin,
while conversion of sodium pentachlorophenate to dioxins occurred at
about 360 C (Langer e_t^ aJU 1973).  Nitric acid converts pentachloro-
phenol to a mixture of tetrachloro-o-and p-quinones (Bevenue and Beck-
man 1967) .
Transport-
Pentachlorophenol was relatively immobile in  acidic Hawaiian soil, but
increasingly mobile as pH increased  (Green and Young 1971) .  In sandy
                                   588
-------
paddy soil, sodium pentachlorophenate leached more readily than PCP
(Asa and Sakamoto 1963) .  PCP soil penetration was greater in xylenol
emulsions than in oil emulsions (Sakagami et al. 1963).
Transport of pentachlorophenol or its salts into water was demonstra-
ted by the presence of 0.1 to 0.7 ppb of pentachlorophenol in the Wil-
lamette River above Corvallis while the effluent from sewage treatment
plants in three Oregon cities contained one to four parts per billion
PCP in the water (Buhler et^ al. 1973).
Persistence-
The effectiveness of PCP decreased with decreasing pH between pH 3 and
pH 8 and also decreased with increasing organic matter content of the
soil and with increasing soil surface area (Su and Lin 1970).  Adsorp-
tion to soil was positively correlated with soil organic matter, pH,
and cation exchange capacity, and negatively correlated with clay con-
tent and bioactivity (Tsunoda 1965).  Choi and Aomine  (1972) also noted
that pentachlorophenol was less effective and more persistent in acid
than in neutral soil, but there was no correlation in their study be-
tween activity and the amount of clay, type of clay, or cation exchange
capacity of the soil once the effects of pH and solubility were elimi-
nated.  Low pH apparently decreased toxicity by decreasing the solubi-
lity of pentachlorophenol.  Sodium pentachlorophenate was less soluble
in humus-rich than in mineral soils, as would be expected of a lipid-
immiscible compound.
Treatment with 15 kg/ha of technical pentachlorophenol resulted in
soil residues of 20.4 ppm of pentachlorophenol and 0.5 ppm of its im-
purity, hexachlorobenzene.  The corresponding residues in lettuce were
0.73 ppm and 0.01 ppm of PCP and hexachlorobenzene, respectively (Casa-
nova and Dubroca 1973).  No degradation of either pentachlorophenol or
sodium pentachlorophenate was observed after twelve months when these
compounds were applied to warm, moist soil, but fixation to the clay
fraction of the soil was not found (Harvey and Crafts 1952).  Penta-
                                  589
-------
chlorophenol applied to soil as a termiticide at an unspecified level
persisted for more than five years (Hetrick 1952).
Effects on Non-Target Species-
Microorganisms—Data on the toxicity of pentachloropheriol to microor-
ganisms are summarized in Table 90.  On soil derived from volcanic ash,
pentachlorophenol was the strongest inhibitor of nitrification among
eight herbicides tested.  In increasing order of toxicity, the compounds
were:  Prometryne < lenacil < diphenamid < trifluralin < vernolate
< MCPA < SWEP < pentachlorophenol.  Pentachlorophenol was the only com-
pound to prevent oxidation of nitrite to nitrate as well as nitrite
formation from ammonium ion (Noguchi and Nakazawa 1971).
Invertebrates—Pentachlorophenol applied at 2.5 to 4 kg/ha decreased
the number of earthworms (species not identified) in the top ten cen-
timeters of soil by 50 percent (Kononova and Kazimirchuk 1970).  In
sea urchin eggs (Ardbaa'ia), pentachlorophenol inhibited mitoses and
disturbed the structure of the mitotic spindle (Sawada and Rebhun
1969).  No embryos of clams (Mereenaria mevcenaria) or oysters (Cras-
sostrea vipginicoC) exposed to 0.25 ppm sodium pentachlorophenate sur-
vived, nor did eggs of either species hatch when exposed to 0.025 ppm
sodium pentachlorophenate.  At the lower dose, 41 percent of oyster
larvae survived (Davis and Hidu 1969).
Vertebrates—The 24 hour LC,-^ of sodium pentachlorophenate for rain-
bow trout (Salmo gairdnerii) was 0.26 ppm; for guchi fish (Naibea al-
biflora), 0.09 ppm (Pimentel 1971).  Bevenue and Beckman (1967) re-
viewed the toxicology of pentachlorophenol to fish.
In birds, the LDcn for five days' treated feed followed by three days'
clean feed was 4,000 to 5,000 mg/kg pentachlorophenol in pheasants,
and 5,000 to 6,000 mg/kg in coturnix quail (Pimentel 1971).
The acute oral LD   of pentachlorophenol was 27 to 80 mg/kg in rats,
while that of sodium pentachlorophenate was 210 mg/kg  (Pimentel 1971).
                                   590
-------



















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Tilemans and Dormal (1952) cited a human acute oral LD   of 275 mg/kg.
Izeke and Iwao (1956)  calculated an acute oral LD-n of 199 mg/kg for
mice.  Dermal toxicity is also well known (Bevenue and Beckman 1967).
Pentachlorophenol was markedly less toxic in rabbits at 8 C than at
36 C (Keplinger et al. 1959).   The biochemical basis of the toxicity
of pentachlorophenol is its capacity to uncouple oxidative phosphory-
                           -6       -4              -4        -3
lation at concentrations 10   to 10  M.  Between 10  M and 10  M, pen-
tachlorophenol also inhibits mitochondrial ATPase, and at levels above
  _3
10  M, PCP inhibits glycolytic phosphorylation, inactivates respira-
tory enzymes, and causes gross damage to mitochondrial structures
(Weinbach 1957).   No data pertaining to carcinogenesis, mutagenesis,
or teratogenesis of PCP were available.
Conclusions-
Sufficiently little is known about the degradation of pentachlorophenol
that any method of disposal is a gamble.  The few available data make
it obvious, however, that biodegradation rarely includes ring cleavage.
Soil disposal is therefore inadvisable unless the nature, toxicity,
and persistence of the terminal residues are elucidated.  Similarly,
in the absence of extensive data on the nature, quantity, toxicity,
and persistence of the dioxins produced by pyrolysis of PCP over a
wide range of temperatures, no conclusions can be drawn as to the feas-
ibility of burning this compound.
                                  592
-------
References
Abedi, Z. H. and W. P. McKinley; 1967.  Bioassay of captan by zebra
  fish larvae.  Nature 216:1321-1322.
Adema, D. M. M., G. M. Meijer and H. J. Hueck; 1967.  The biological
  activity of pentachlorophenol esters.  Intern. Biodeterior Bull.
  3:29-32. (Chem. Abstr. 67:107595h, 1967).
Agnihotri, V. P.; 1970.  Persistence of captan  N-(trichloromethylthio)
  4-cyclohexene-l,2-dicarboximide  and its effect on microflora, res-
  piration and nitrification of a forest nursery soil.  Can. J. Micro-
  biol. 17:377-383.
Ahlborg, U. G. and J. E. Lindgren; 1974.  Metabolism of pentachloro-
  phenol.  Arch. Toxicol. 32:271-281.
Allsopp, D., H. J. Hueck, H. 0. W. Eggins and A. 0. Lloyd; 1970.
  Evidence of the hydrolysis of pentachlorophenyl laurate by soil
  microorganisms.  J. Text. Inst. 61:509-511. (Chem. Abstr. 74:12097c,
  1971).
Andianova, M. M. and I. V. Alekseev; 1970.  Carcinogenic properties of
  the pesticides Sevin, maneb, ziram, zineb.  Vop. Pitan. 29:71-74.
  (Chem. Abstr. 74:85626j, 1971).
Anderson, M. D. and H. S. Rosenkranz; 1974.  Greenhouse fungicide.
  Environmental carcinogen.  Henry Ford Hosp. Med. J. 22:35-40. (Chem.
  Abstr. 82:27890h, 1975).
Aso, S. and T. Sakamoto; 1963.  Pentachlorophenol under paddy field
  conditions.  I. Differences of behavior of pentachlorophenol among
  several soil types.  Nippon Dqjo-Hiryogaku Zasshi 34(5):164-168.
  (Chem. Abstr. 61:12564h, 1964).
Balin, P. N.; 1970.  Experimental data on the blastomogenic activity
  of the fungicide, maneb.  Vrach. Delo. 4:21-24. (Chem. Abstr. 73:
  34122p, 1970).
                                 593
-------
Bancroft, R. and K. V. Prahlad; 1973.  Effect of ethylenebis(dithio-
  carbamic acid) disodium salt (nabam) and ethylenebis(dithiocarba-
  mato) manganese (maneb) on Xenopus laevis development,  Teratology
  7:143-150.
Beran, F. and J. Neururer; 1956.   Action of plant protectants on the
  honeybee (Apis m&llifera').  II. Toxicity of plant protection agents
  to bees.  Pflanzenschutz Ber. 17:113-390. (Chem. Abstr. 51:6933i,
  1957).
Betts, J. J. , S. P. James and W.  V. Thorpe; 1955.  Metabolism of pen-
  tachloronitrobenzene and the formation of mercapturic acids in the
  rabbit.  Biochem. J. 61:611-617.
Bevenue, A. and H. Beckman; 1967.  Pentachlorophenol:   a discussion of
  its properties and its occurence as a residue in human and animal
  tissues.  Residue Reviews 19:83-134.
Bontoyn, W. R. and J. B. Looker;  1973.  Degradation of commercial
  ethylenebisdithiocarbamate formulations to ethylenethiourea under
  elevated temperature and humidity.  J. Agr. Food Chem., 21:338-341.
Bridges, B. A.; 1975.  The mutagenicity of captan and  related fungi-
  cides.  Mutat. Res. 32:3-34.
Bridges, B. A., R. P. Mottershead, M. A. Rothwell and  M. H. L. Green;
  1972.  Repair deficient bacterial strains suitable for mutagenicity
  screening.  Tests with the fungicide captan.  Chem.-Biol. Interac-
  tions 5:77-84.
Bridges, B. A., R. P. Mottershead and C. Colella; 1973.  Induction of
  forward mutations to colicin £„ resistance in repair deficient strains
  of Escheriehia coli.  Experiments with ultraviolet light and captan.
  Mutat. Res. 21:303-313.
Buhler, D. R., M. E. Rasmusson and H. S. Nakave; 1973.  Occurrence of
  hexachlorophene and pentachlorophenol in sewage and  water.  Environ.
  Sci. Technol. 7:929-934.
Burchfield, H. P.; 1959.  Comparative stabilities of Dyrene, 1-fluoro-
  2,4-dinitro-benzene, dichlone and captan in a silt loam soil.  Con-
  tribs. Boyce Thompson Inst. 20:205-215.
                                  594
-------
Buselmaier, W., G. Roehrborn and P. Propping; 1972.  Mutagenitats-
  Untersuchungen mit Pestiziden im Host-mediated assay und mit dem
  Dominanten Lethaltest an der Maus.  Biol. Zentralbl. 91:311-325.
Capriotti, A. and A. Martini; 1959.  Effect of modern weed killers,
  insecticides and fungicides on the soil microflora. III. Fungi-
  cides.  Ann. Fac. Agrar. Univ. Studi Perugia 14:95-105. (Chem.
  Abstr. 57:10285d, 1962).
Casanova, M. and J. Dubroca; 1973.  Residues of pentachloronitroben-
  zene and its hexachlorobenzene impurity in soils and lettuce.  C. R.
  Seances Acad. Agr. Fr. 58:990-998. (Chem. Abstr. 79:1062q, 1973).
Chaigneau, M. , G. LeMoan and L. Giry; 1966.  Decomposition pyroge'ne'e
  du bromure de me'thyle en 1'absence d'oxygene et h 550 C.  Compt.
  Rend. Ser. C. 263:259-261.
Chandra, P. and W. B. Bollen; 1961.  Effects of nabam and mylone on
  nitrification, soil respiration, and microbial numbers in four Oregon
  soils.  Soil Sci. 92:387-393.
Chepinoga, 0. P., 0. V. Chernov, L. V.  Samosh, P. N. Balin, I. I.
  Khitsenko, M. A. Pilinskaya, L. V. Martson, N. A. Zadorozhnaya, N. P.
  Zastavnyuk and A. I. Kurinnoi; 1970.   Possible blastomogenic, muta-
  genic, and embryotropic effects of some carbamate pesticides.  Vop.
  Gig. Toksikol. Pestits., Tr. Nauch. Sess. Akad. Med. Nauk SSSR 1967,
  129-134. (Chem. Abstr. 74:123308s, 1971).
Chernov, 0. V.; 1972.  Blastemogenic properties of some derivatives of
  dithiocarbamic acid and their metabolites.  Onkologiya 123-126.
  (Chem. Abstr. 79:62413b, 1973).
Chernov, 0. V. and I. I. Khitsenko; 1969.  Blastomogenic properties of
  some derivatives of dithiocarbamic acid (herbicides, zineb and ziram).
  Vop. Onkol. 15:71-74. (Chem. Abstr. 71:21105w, 1969).
Chinn, S. H. F.; 1973.  Effect of eight fungicides on microbial acti-
  vities in soil or measured by bioassay method.  Can. J. Microbiol.
  19:771-777.
                                  595
-------
Chisholm, R. D. and L. Koblitsky; 1943.  Sorption of MeBr by soil in a
  fumigation chamber.  J. Econ. Entomol, 36:549-551.
Choi, J. and S. Aomine; 1972.  Effect of the soil on the activity of
  pentachlorophenol.  Soil Sci. Plant Nutr. 18:255-260.
Chu, J. R. and E. J. Kirsch; 1972.  Metabolism of pentachlorophenol by
  an axenic bacterial culture.  Appl. Microbiol. 23:1033-1035.
Clarke, C. H.; 1971.  Mutagenic specificities of pentachloronitroben-
  zene and captan, two environmental mutagens.  Mutat. Res. 11:247-248.
Cole, H., D. Mackenzie, C. B. Smith and E. L. Bergman; 1968.  Influence
  of various soil-incorporated fungicides and nematocides on macro-
  and microelement constituents of Zea Mays and Phaseolus vulgar-is.
  Bull. Environ. Contain. Toxicol. 3:116-126.
Corden, M. E. and R. A. Young; 1965.  Changes in the soil microflora
  following fungicide treatments.  Soil Sci. 99:272-277.
Cox, C. E., H. D. Sisler and R. A. Spurr; 1951.  Identity of gaseous
  toxicants from organic sulfur fungicides.  Science 114:643-645.
Crosby, D. G. and N. Hamadmad; 1971.  Photoreduction of pentachloroben-
  zenes.  J. Agr. Food Chem. 19:1171-1174.
Cserjesi, A. J.; 1967.  The adaptation of fungi to pentachlorophenol
  and its biodegradation.  Can. J. Microbiol. 13:1243-1249.
Curtis, R. F., D. G. Land, N. M. Griffiths, M. Gee, D. Robinson, J. L.
  Peel, C. Dennis and J. M. Gee; 1972.  2,3,4,6-Tetrachloroanisole
  association with musty taint in chickens and microbiological forma-
  tion.  Nature 235:223-224.
Davis, H. C. and H. Hidu; 1969.  Effects of pesticides on embryonic
  development of clams and oysters, and on survival and growth of the
  larvae.  U.S. Fish Wildl. Serv., Fish. Bull. 67:393-404.
DeBaun, J. R., J. B. Miaullis, J. Knarr, A. Mihailovski and J. J. Menn;
                              14
  1974.  Fate of N-trichloro-   C -methylthio-4-cyclohexene-l,2-dicar-
            14
  boximide (  C-captan) in the rat.  Xenobiotica 4:101-119.
Didenko, G. G. and T. D. Gupalovich; 1975.  Activity of deoxyribonucl-
  ease and hexokinase in blood serum of mice exposed to the effect of
                                  596
-------
  urethane and some pesticides.  Vopr. Onkol. 21:57-60. (Chem. Abstr.
  82:150264w, 1975).
Domsch, K. H.; 1959.  Die Wirkung von Bodenfungiciden.  III. Quantita-
  tive Veranderungen der Bodenflora.  Z. Pflanzenkrankheiten u. Pflan-
  zenschutz 66:17-26.
Domsch, K. H.; 1964.  Der Einfluss von fungiziden Wirkstoffen auf die
  Bodenatmung.  Phytopathol. Z. 49:291-302.
Donev, L. and Z. Zareva-Tomaleva; 1968.  Effect of some pesticides on
  soil microflora.  Prikl. Biokhim. Mikrobiol. 4:408-412.  (Chem. Abstr.
  69:75865u, 1968).
Dowe, T. W. , J. Matsushima and V. H. Arthaud; 1957.  The effects of
  corn treated with fungicides upon the performance of fattening
  steers.  J. Animal Sci. 16:93-99.
Dubey, H. D. and R. L. Rodriguez; 1970.  Effect of dyrene and maneb on
  nitrification and ammonification, and their degradation in tropical
  soils.  Soil Sci. Soc. Amer., Proc. 34:435-439.
Dubey, H. D. and R. L. Rodriguez; 1974.  Changes in soil microflora
  following application of fungicides Dyrene and maneb to tropical
  soils.  J. Agr. Univ. P. R. 58:78-86.
Dugger, W. M., Jr., T. E. Humphreys and B. Calhoun; 1958.   Influence
  of captan on higher plants.  I. Effect on the morphology and gross
  metabolism of root tissue.  Am. J. Botany 45:683-687.
Dumas, T.; 1973.  Inorganic and organic bromide residues in foods fu-
  migated with methyl bromide and ethylene dibromide at low tempera-
  tures.  J. Agr. Food Chem. 21:433-436.
Eichelberger, J. V. and J. J. Lichtenberg; 1971.  Persistence of pes-
  ticides in river water.  Environ. Sci. Technol. 5:541-544.
Engst, R.; 1970.  Metabolism of fungicide ethylenebis(dithiocarbamates)
  and its dietary and toxicologic significance.  Hrana Ishrana 11:32-
  36. (Chem. Abstr. 73:130066u, 1970).
Engst, R.; 1971.  Zum Metabolismus ausgewahlter Pflanzenschutz- und
  Schadlingsbekamp-fungsmittel.  Nahrung 15:815-825.
Engst, R. and W. Schnaak; 1967.  Metabolism of the fungicidal ethyle-
  nebis(dithiocarbamates), maneb and zineb.  I. Identification and
                                 597
-------
  fungitoxic activity in a model experiment of synthesized metabolites.
  Z. Lebensm.-Unters.-Forsch. 134:216-221. (Chem. Abstr. 67:116087w,
  1967).
Engst, R. and W. Schnaak; 1970.  Metabolism of the fungicidal ethylene-
  bis(dithiocarbamates), maneb and zineb.  III. Pathways of degradation.
  Z. Lebensm.-Unters.-Forsch. 143:99-103. (Chem. Abstr. 73:108724k, 1970)
Engst, R. and W. Schnaak; 1974.  Residues of dithiocarbamate fungicides
  and their metabolites on plant foods.  Residue Reviews 52:45-67.
Fuhr, I., A. V. Bransford and S. D. Silver; 1948.  Sorption of fumigant
  vapors by soil.  Science 107:274-275.
Gaeb, S., S. Nitz, H. Parlar and F. Korte; 1975.  Beitrage zur okolo-
  gischen Chemie CV:  Photomineralization of certain aromatic xeno-
  biotica.  Chemosphere 4:251-256.
Gaines, T. B.; 1969.  Acute toxicity of pesticides.  Toxicol. Appl.
  Phannacol. 14:515-534.
Ghizelea, G.; 1973.  Effect of carbamic pesticides, zineb and thiuram,
  upon the estrous cycle and the reproduction capacity of the white
  rat.  Stud. Cercet. Endocrinol. 24:491-501. (Chem. Abstr. 80:
  128956k, 1974).
Goldberg, M. C. and R. L. Wershaw; 1965.  Biodegradation of dodecyl-
  guanidine acetate (dodine).  Amer. Chem. Soc. Div. Air Waste Chem.,
  Preprints.  5:53-56. (Chem. Abstr. 66:54482q, 1967).
Goring, C. A. I., D. A. Laskowski, J. W. Hamaker and R. W. Meikle; 1975.
  in:  Environmental Dynamics of Pesticides, 135-172.  Principles of
  pesticide degradation in soil.  R. Haque and V. H. Freed, eds.; Ple-
  num Press, N.Y.
Grabarska, A.; 1972.  Changes in internal organs of rabbits after ex-
  perimental oral administration of captan fungicide.  Zesz. Nauk.
  Wyzsz, Szk. Roln. Olsztynie.  28:279-284.  (Chem. Abstr. 79:28122w,
  1973).
                                   598
-------
Grandi, L., A. Corte and R. Ciferri; 1958.  Degradation of zineb and
  ziram at various temperatures as a function of time.  Nitoz. Mai.
  Piante.  43-44:52-65. (Chem. Abstr. 52:20839i, 1958).
Green, R. E. and R. H. I. Young; 1971.  Herbicide and fertilizer move-
  ment in Hawaiian sugarcane soils in relation to subsurface water
  quality.  Hawaii Sugar Technol., Rep. 29:88-96. (Chem. Abstr. 75:
  75400r, 1971).
Griffith, R. L. and S. Matthews; 1969.  Persistence in soil of the
  fungicidal seed dressings captan and thiram.  Ann. Appl. Biol. 64:
  113-118.
Halleck, F. E. and V. W. Cochrane; 1950.  Effect of fungostatic agents
  on the bacterial flora of the rhizosphere.  Phytopathology 40:715-
  718.
Hansen, J. C.; 1972.  Effect of some sulfur- and mercury-containing
  fungicides on bacteria.  Chemosphere 1:159-162.
Harvey, W. A. and A. S. Crafts; 1952.  Toxicity of pentachlorophenol
  and its sodium salt in three Yolo soils.  Hilgardia 21:487-498.
Hermanutz, R. 0., L. H. Mueller and K. D. Kempfert; 1973.  Captan tox-
  icity to fathead minnows (Pimiphales promelas), bluegills (Lepomis
  macroahivus) and brook trout (Salvelinus fontinal-is).  J. Fish Res.
  Board Can. 30:1811-1817.
Hetrick, L. A.; 1952.  The comparative toxicity of some organic insec-
  ticides as termite soil poisons.  J. Econ. Entomol. 45:235-237.
Heungens, A.; 1972.  Influence of methyl bromide on the soil fauna in
  pine litter.  Rev. Agr.  (Brussesl) 25:401-403.
Hiatt, C. W., W. T. Haskins and L. Olivier; 1960.  The action of sun-
  light on sodium pentachlorophenate.  Am. J. Trop. Med. Hyg.  9:527-
  531.
Hubbell, D. H., D. F. Rothwell, W. B. Wheeler, W. B. Tappan and F. M.
  Rhoads; 1973.  Microbiological effects and persistence fo some pes-
  ticide combinations in soil.  J. Environ. Qual. 2:96-99.
                                 599
-------
Hylin, J. W.;  1973.  Oxidative decomposition of ethylenebis(dithiocar-
  bamates).   Bull. Environ. Contam. Toxicol. 10:227-233.
Ide, A., Y.  Niki, F. Sakamoto, I. Watanabe and H. Watanabe; 1972.  De-
  composition of pentachlorophenol in paddy soil.  Agr. Biol. Chem.
  36:1937-1944.
Iley, J. R.  and J. G. A. Fiskell; 1963.  Degradation of zineb by sun-
  light and in soil cultures.  Soil Crop Sci. Soc. Florida, Proc. 23:
  50-61. (Chem. Abstr. 62:2194b, 1965).
Ivanova, L., G. Dimov and N. Masheva; 1966.  Experimental substantia-
  tion of the maximum permissable concentration of zineb in the air of
  the working premises.  Khig. Zdraveopazvane.  9:483-491. (Chem.
  Abstr. 66:11855a, 1967).
Izeki, M. and M. Iwao; 1956.  Antiseptics.  Sodium pentachlorophenol.
  J. Osaka City Med. Center 5:119-124. (Chem. Abstr. 50:15960b, 1956).
                                                  14
Jakobsen, I. and S. Yllner; 1971.  Metabolism of (  C)-pentachloro-
  phenol in the mouse.  Acta Pharmacol. Toxicol. 29:513-524.
Jenkinson, D.  S. and D. S. Powlson; 1970.  Residual effects of soil
  fumigation on soil respiration and mineralization.  Soil Biol. Bio-
  chem. 2:99-108.
Johnson, D.  F.; 1954.  A toxicity test of N-(trichloromethylthio)tetra-
  hydrophthalimide.  Southwestern Veterinarian.  8:30-32.
Jones, K. H.,  D. M. Sanderson and D. N, Noakes; 1968.  Acute toxicity
  data for pesticides  (1968).  World Rev. Pest. Contr. 7:135-143.
Kada, T., M. Moriya and Y. Shirasu; 1974.  Screening of pesticides for
  DNA interactions by rec-assay and mutagenesis testing, and frame-
  shift mutagens detected.  Mutat. Res. 26:243-248.
Karpenko, V. N.; 1975.  Effect of the dithiocarbamate pesticides zineb,
  maneb, and polymarzin on the blood coagulation system.  Vrach. Delo
  1:122-124.  (Chem. Abstr. 83:54227m, 1975).
Kaufman, D.  D.; 1974.  in:  Pesticides in Soil and Water.  133-202.
  Degradation of pesticides by soil microorganisms.  W. D. Guenzi, ed.
  Soil Sci.  Soc. Am., Madison, Wisconsin.
                                 600
-------
Kempton, R. J. and G. A. Maw; 1973.  Soil fumigation with methyl bro-
  mide.  Uptake and distribution of inorganic bromide in tomato plants.
  Ann. Appl. Biol. 74:91-98.
Keplinger, M. L., G. E. Lanier and W. B. Deichmann; 1959.  Effects of
  environmental temperature on the acute toxicity of a number of com-
  pounds in rats.  Toxicol. Appl. Pharmacol. 1:156-161.
Kennedy, G. L., Jr., D. W. Arnold and M. L. Keplinger; 1975.  Mutageni-
  city studies with captan, captofol, folpet, and thalidomide.  Food
  Cosmet. Toxicol. 13:55-61.
Kennedy, G., 0. Fancher and J. C. Calandra; 1968.  Teratogenic poten-
  tial of captan, folpet and difolatan.  Toxicol. Appl. Pharmacol. 13:
  420-430.
Kennedy, G. L., Jr., 0. E. Fancher and J. C. Calandra; 1975.  Nontera-
  togenecity of captan in beagles.  Teratology 11:223-225.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1972a.   Chemi-
  cal and thermal aspects of pesticide disposal.  J. Environ. Qual. 1:
  63-65.
Kennedy, M. V., B. J. Stojanovic and F. L. Shuman, Jr.; 1972b.  Analy-
  sis of decomposition products of pesticides.  J. Agr. Food Chem. 20:
  341-343.
Khera, K. S.; 1973.  Ethylenethiourea:  Teratogenicity study in rats
  and rabbits.  Teratology 7:243-252.
Kittleson, A. R.; 1953.  Preparation and some properties of ff-(tri-
  chloromethylthio) phthalimide.  J. Agr. Food Chem. 1:677-679.
Klisenko, M. A. and M. S. Vekshtein; 1971.  Kinetics of hydrolysis of
  metal derivatives of dialkyl- and ethylenebis(dithiocarbamic acids)
  as a function of pH and identification of their reaction products.
  Zh. Obshch. Khim. 41:1122-1127. (Chem. Abstr. 75:87761u, 1971).
Kluge, E.; 1969a.  Duration of the effect of thiuram, ferbam, and cap-
  tan in forest soils.  Arch. Pflanzenschutz.  5:39-53. (Chem. Abstr.
  71:69579d, 1969).
Kluge, E. ; 1969b.  Effect of the soil reaction on decomposition and
  persistency of thiuram, ferbam and captan in the soil.  Arch. Pflan-
                                  601
-------
  zenschutz.  5:263-271. (Chem. Abstr. 73:24214f, 1970).
Kobayashi, K. and H. Akitake; 1975a.  Metabolism of chlorophenols in
  fish.  I. Absorption and excretion of pentachlorophenol by goldfish.
  Nippon Suisan Gakkaishi 41:87-92. (Chem. Abstr. 82:107212r, 1975).
Kobayashi, K. and H. Akitake; 1975b.  Metabolism of chlorophenols in
  fish.  II. Turnover of absorbed pentachlorophenol in goldfish.
  Nippon Suisan Gakkaishi. 41:93-99. (Chem. Abstr. 82:107212r, 1975).
Kobrinsky, P. C. and R. M. Martin; 1968.  High-energy methyl radicals;
  the photolysis of methyl bromide at 1850 A.  J. Chem. Phys. 48:5728-
  5729.  (Chem. Abstr. 69:66698q, 1968).
Kononova, N. E. and L. P. Kazimirchuk; 1970.  Effect of chemical treat-
  ments on forest soil and its fauna.  Zashch. Rast. (Kiev) 11:6-10.
  (Chem. Abstr. 77:57539b, 1972).
Kratochvil, D. E.;  1951.  Determination of the effect of several her-
  bicides on soil microorganisms.  Weeds 1:25-31.
Krister, C. J. ; 1952.  Residues of dithiocarbamate fungicides on food
  crops.  Agr. Chemicals 7(9):45-48.
Krolikowska-Prasal, I.; 1973.  Cytochemical studies on the effect of
  captan on the metabolism of liver cells.  Ann. Univ. Mariae Curie-
  Sklodowska, Sect. D. 28:81-90. (Chem. Abstr. 83:54194y, 1975).
Kuitnitskaya, V. A. and T. S. Kolesnichenko; 1971.  Transplacental
  blastomogenic action of zineb on the progeny of mice.  Vop. Pitan 30:
  49-50. (Chem. Abstr. 74:110760h, 1971).
Kurinnyi, A. I. and T. I. Kondratenko: 1972.  Effect of fungicides
  (dithiocarbamic acid derivatives) on chromosomes of bone marrow cells
  in mice.  Tsitol. Genet. 6:225-228. (Chem. Abstr. 77:110245f, 1972).
Lange, P., W. D. Wiezorek and M. Witt; 1975.  Effects of diethyldithio-
  carbamate on acute toxicity and acetylcholinesterase inhibition by
  methyl parathion in mice.  Acta Biol. Med. Ger. 34:427-433. (Chem.
  Abstr. 83:54262u, 1975).
Langer, H. B., T. P. Brady, L. A. Dalton, T. W. Shannon and P. R.
  Briggs; 1973.  Thermal chemistry of chlorinated phenols.  Advan.
  Chem. Ser. 120:26-32.
                                 602
-------
Langkramer, 0.; 1970.  Feststellung des Einflusses von Pestiziden auf
  Bodenmikroorganismen in Reinkulturen mit Hilfe einer Laboratoriums-
  methode.  Zentralbl. Bakteriol., Parasitenk., Infektionskr., Hyg.,
  Abt. 2. 125:713-722.
Langkramer, 0.; 1972.  Laboratory method for determining the  effects of
  pesticides on soil microorganisms in pure cultures.  Agrochemia 12:
  193-199. (Chem. Abstr. 77:135857v, 1972).
Legator, M. S., F. J. Kelly, S. Green and E. J. Oswald; 1969.  Muta-
  genic effects of captan.  Ann. N.Y. Acad. Sci. 160:344-351.
Levinskas, G. J., L. B. Vidone, J. J. O'Grady and C. B. Shaffer; 1961.
  Acute and chronic toxicity of dodine.  Toxicol. Appl. Pharmacol. 3:
  127-142.
Lyr, H.; 1963.  Enzymic detoxification of chlorinated phenols.  Phyto-
  pathol. Z.  47, No. 1:73-83.
Malkomes, H.  P.; 1972.  Der Einfluss von Bodenbegasungen mit Methyl-
  bromid  (Terabol) auf gartnerische Kulturpflanzen. II. Bromidaufnahme
  und—toleranz bei Gemiisepflanzen.  Z. Pflanzenkr. Pflanzenschutz 79:
  321-338.
Martin, H.; 1968.  Pesti-o-ide Manual.  British Crop Protection Council.
Martson, L. V.; 1969.  Effect of maneb on the embryonic development
  and generative function of rats.  Farmakol. Toksikol. 32:731-732.
  (Chem. Abstr. 72:65870q, 1970).
Matsuguchi, T. and S. Ishizawa; 1968.  Effect of agrochemicals on mi-
  croorganisms and their activities in soils.  I. Pentachlorophenol
  (PCP).  Nippon Dojo-Hiryogaku Zasshi 39:241-246. (Chem. Abstr. 69:
  66526g, 1968).
McClellan, W. D., J. R. Cristie and N. L. Horn; 1949.  Efficacy of
  soil fumigants as affected by soil temperature and moisture.  Phyto-
  pathology 39:272-283.
McTigue, P. T. and A. S. Buchanan; 1959.  Photolysis of methyl in the
  presence of metals.  II. Methyl bromide.  Trans. Faraday Soc. 55:
  1160-1164.
                                  603
-------
Moore, R. B.; 1970.  Effects of pesticides on growth and survival of
  Euglena gvaoilis Z.  Bull. Environ. Contam. Toxicol. 5:226-230.
Munakata, K. and M. Kuwahara; 1969.  Photochemical degradation products
  of pentachlorophenol.  Residue Reviews 25:13-23.
Munnecke, D. E.; 1958.  Persistence of nonvolatile diffusible fungi-
  cides in soil.  Phytopathology 48:581-585.
Munnecke, D. E.; 1961.  Movement of nonvolatile, diffusible fungicide
  through columns of soil.  Phytopathol. 51:593-599.
Munnecke, D. E., K. H. Domsch and J. W. Eckert; 1962.  Fungicidal ac-
  tivity of air passed through columns of soil treated with fungicides.
  Phytopathology 52:1298-1306.
Naumann, K.; 1970.  Soil microflora after application of the fungi-
  cides, olpisan (trichlorodinitrobenzene), captan, and thiuram.  Arch.
  Pflanzenschutz. 6:383-398. (Chem. Abstr. 74:110793w, 1971).
Nazarov, S. S.; 1966.  Laboratory and field toxicity of new insecti-
  cides, fungicides, and herbicides for bees.  Tr. Nauch.-Issled. Inst.
  Pchelovod. 1966, 398-416. (Chem. Abstr. 70:35489p, 1969).
Nesheim, 0. N. and M. B. Linn; 1968.  The fungitoxicity of thiram,
  captan, and Chemagro 2635 in relation to organic matter and clay
  content of soil.  Trans. 111. State Acad. Sci. 61:26-30.
Newsome, W. H., J. B. Shields and D. C. Villeneuve; 1975.  Residues of
  maneb, ethylenethiuram monosulfide, ethylenethiourea, and ethylene-
  diamine on beans and tomatoes field treated with maneb.  J. Agr.
  Food Chem. 23:756-758.
Noguchi, K. and A. Nakazawa; 1971.  Effects of herbicides on soil en-
  vironment.  Effects on soil nitrification.  Zasso Kenkyu 64-68.
  (Chem. Abstr. 77:71343q, 1972).
Overman, A. J.; 1972.  Effect of fumigants on nontarget soil microor-
  ganisms in tomato seedbeds.  Soil Crop Sci. Soc. Fla. Proc. 31:256-
  260. (Chem. Abstr. 80:91821j, 1974).
Palmer, J. S. and R. D. Radeleff; 1964.  The toxicologic effects of
  certain fungicides and herbicides on sheep and cattle.  Ann. N.Y.
  Acad. Sci. 111:729-736.
                                  604
-------
Petrosini, G.; 1962.  Natural degradation of dithiocarbamates (fungi-
  cides).  Notiz. Mai. Piante. 59-60:59-66. (Chem. Abstr. 57:8957f,
  1962).
Petrosini, G. and F. Tafuri; 1964.  Decomposition products of the alky-
  lenebis(dithiocarbamates).  Atti Symp. Intern. Agrochim. 5:630-640.
  (Chem. Abstr. 64:12546b, 1966).
Petrova-Vergieva, T. and L. Ivanova-Chemishanska; 1971.  Teratogenic
  effect of zinc ethylenebis(dithiocarbamate) (zineb) in rats.  Eksp.
  Med. Morfol. 10:226-230. (Chem. Abstr. 76:149708p, 1971).
Petrova-Vergieva, T. and L. Ivanova-Chemishanska; 1973.  Assessment of
  the teratogenic activity of dithiocarbamate fungicides.  Food Cos-
  met. Toxicol. 11:239-244.
Pfeifer, F. T. and G. Pfeifer; 1970.  Thermal decomposition of fungi-
  cides of the phthalimide type.  Proc. Anal. Chem. Conf., 3rd.   2:
  371-377. (Chem. Abstr. 74:52423n, 1971).
Picci, G.; 1956.  Effect of captan on soil microorganisms.  Agr. Ital.
  (Pisa) 56:376-382. (Chem. Abstr. 51:6926g, 1957).
Pilinskaya, M. A.; 1967.  Mutagenic properties of zineb and ziram in
  Drosophila.  Gig. Toksikol. Pestits. Klin. Otravlenii 5:305-311.
  (Chem. Abstr. 71:122773r, 1969).
Pilinskaya, M. A.; 1974.  Results of the cytogenic examination of per-
  sons occupationally in contact with the fungicide zineb.  Genetika
  10:140-146. (Chem. Abstr. 81:67966k, 1974).
Pimentel, D. ; 1971.  Ecological effects of pesticides on non-target
  species.  Exec. Office of the President, Office of Science and Tech-
  nology, U.S. Gov't. Printing Office, Wash., D. C.
Plimmer, J. R. ; 1973.  Technical pentachlorophenol, origin and analy-
  sis of base-insoluble contaminants.  Environ.  Health Perspect. 5:
  41-48.
Pochon, J., J. Lajudie and 0. Coppier; 1951.  Action of certain anti-
  parasitic substances on the microflora of the soil.  Ann. Inst. Pas-
  teur. 80:517-519.
                                  605
-------
Prahlad, K. V., R. Bancrot and L. Hanzely; 1974.  Ultrastructural
  changes induced by the fungicide ethylenebis(dithiocarbamic acid)
  disodium salt (nabam) in Xenopus laevis tissues during development.
  Cytobios 9:121-130. (Chem. Abstr. 81:59000a, 1974).
Pugh, G. J. F.; 1973.  Effect of three fungicides on nitrification and
  ammonification in soil.  Soil Biol. Biochem. 5:577-584.
Rappoport, M. B. , E. I. Makovskaya and R. P. Khaustova; 1966.  Pulmon-
  ary adenomas induced by a zinc dithiocarbamate (zineb).  Vrach, Delo.
  1966:100-104. (Chem. Abstr. 66:9344z, 1967).
Rashev, Z.; 1972.  Cytopathic and cytotoxic action of pesticides on
  cell structures.  Eksp. Med. Morfol. 11:35-39. (Chem. Abstr. 77:
  97462c, 1972).
Reber, H.; 1967.  Vergleichende Untersuchungen zur ToxizitSt und Selek-
  tivitat von Entseuchungsmitteln flir Bodenmikroorganismen.  Z. Pflan-
  zenkr. Pflanzenschutz. 74:414-426.
Rich, S. and J. G. Horsfall; 1950.  Gaseous toxicants from organic sul-
  fur compounds.  Am. J. Botany 37:643-650.
Richmond, D. V. and J. A. Pickard; 1967.  Carbonyl sulfide from the
  decomposition of captan.  Nature 215:214.
Richmond, D. V. and E. Somers; 1968.  The fungitoxicity of captan. VI.
                   35
  Decomposition of   S-labeled captan by Neurospora orassa conidia.
  Ann. Appl. Biol. 62:35-43.
Ryazanov, R. A.; 1967.  Effect of the fungicides ziram and zineb on the
  generative function of test animals.  Gig. Sanit. 32:23-30.  (Chem.
  Abstr. 66:85011q, 1967).
Sakagami, Y., S. Suzuki, T. Ishino, Y. Sugihara and H. Hyuga; 1963.
  Translocation of pentachlorophenol in soil.  Meiji Daigaku Nogakubu
  Kenkyo HOkoku 15:41-46.  (Chem. Abstr. 60:6165b, 1964).
Sanderman, W., K. Stockmann and R. Casten; 1957.  Uber die Pyrolyse
  des Pentachlorophenols.  Chem. Ber. 90:690-692.
Sawada, N. and L. I. Rebhun; 1969.  Effect of dinitrophenol and other
  phosphorylation uncouplers on the firefringence of the mitotic appa-
  ratus of marine eggs.  Exp. Cell. Res. 55:33-38.
                                  606
-------
Seefeld, F. and H. Beitz; 1968.  Dynamics of methyl bromide residue
  deposit in gassed products.  Nachrichtenbl. Deut. Pflanzenschutz-
  dienst. (Berlin) 22:248-252. (Chem. Abstr. 71:37549c, 1969).
Seidler, H., M. Haertig, W. Schnaak and R. Engst; 1970.  Untersuchun-
  gen liber den Metabolismus einiger Insektizide und Fungizide in der
                                            14
  Ratte.  2. Mitt. Verteilung und Abbau von   C-markiertem Maneb.
  Nahrung 14:363-373.
Seidler, H., H. Haertig, W. Schnaak and R. Engst; 1971.  Untersuchun-
  gen iiber den Metabolismus einiger Insektizide und Fungizide in der
                                                          35
  Ratte.  3. Mitt:  Ausscheidung Verteilung und Abbau von   S-markier-
  tem Captan.  Nahrung 15:177-185.
Seiler, J. P.; 1973.  Survey on the mutagenicity of various pesticides.
  Experientia 29:622-623.
Shaw, F. R.; 1959.  The effects of field applications of some of the
  newer pesticides on honeybees.   J. Econ. Entomol. 52:549-550.
Shea, K. P.; 1972.  Captan and folpet.  Environment 14:22-24, 29-32.
Shiroishi, M., A. Hayakowa, K. Okumura and K. Umeda; 1964.  Methyl
  Bromide.  Shokuryo Kenkyusho Kenkyu Hokoku 18:193-199. (Chem. Abstr.
  66:36639s, 1967).
Shpirt, M. B.; 1973.  Toxicological evaluation of the action of DDT,
  hexachlorocyclohexane, tetramethylthiuram, Sevin, and zineb on human
  cell cultures.  Gig. Tr. Prof.  Zabol. (3) 1973:32-35. (Chem. Abstr.
  79:1088c, 1973).
Siebert, D., F. K. Zimmermann and E. Lemperle; 1970.  Genetic effects
  of fungicides.  Mutat. Res. 10:533-543.
Slifkin, M. K.; 1973.  Apparent induction of mutants and enhancement
  of conidial formation by fungicides in A.lter'nar'la malt.   Mycopathol.
  Mycol. Appl. 50:233-240.
Boeder, C. J., R. Liersch and U.  Trueltzsch; 1969.  Unterschiedliche
  Wirkung von Captan auf das Wachstum einiger Stamme von Chlovella
  und Scenedesmus.  Arch. Mikorbial 67:166-172.
Somers, E. and R. J. Pring; 1966.  Uptake and binding of dodine acetate
  by fungal spores.  Ann. Appl. Biol. 58:457-466.
                                 607
-------
Somers, E., D. V. Richmond and J. A.  Pickard; 1967.   Carbonyl sulfide
  from the decomposition of captan.   Nature 215:214.
Stehl, R. H.,  R. R. Papenfuss, R. A.  Bredeweg and R.  W.  Roberts; 1973.
  Stability of pentachlorophenol and  chlorinated dioxins to sunlight,
  heat, and combustion.  Advan. Chem. Ser.  120:119-125.
Stojanovic, B. J., M. V. Kennedy and  F.  L.  Shuman, Jr.;  1972a.   Edaphic
  aspects of the disposal of unused pesticides,  pesticide wastes and
  pesticide containers.  J. Environ.  Qual.  1:54-62.
Stojanovic, B. J., F. Hutto, M. V. Kennedy and F. L.  Shuman, Jr.; 1972b.
  Mild thermal degradation of pesticides.   J. Environ.  Qual. 1:397-401.
Su, Y. and H.  Lin; 1970.  Influence of soil physiochemical character-
  istics on the efficacy of herbicide pentachlorophenol.  Chung. Kuo
  Nung Yeh Hua Hsueh Hui Chih 8:99-104.  (Chem. Abstr. 74:110707w, 1971).
Suzuki, T. and K. Nose; 1970.  Decomposition of pentachlorophenol in
  farm soil.  I. Factors relating to  pentachlorophenol decomposition.
  Noyaku Seisan Gijutsu 22:27-30. (Chem. Abstr.  76:13140q, 1972).
Suzuki, T. and K. Nose; 1971.  Decomposition of pentachlorophenol in
  farm soil.  II. PCP metabolism by a microorganism isolated from soil.
  Noyaku Seisan Gijutsu. 26:21-24. (Chem.  Abstr. 77:4204g, 1972).
Tews, L. L.; 1971.  Effects of selected  fungicides and soil fumigants
  upon the microfungi of a cattail marsh.   Proc. Conf.  Gt. Lakes Res.,
  14th.  128-136. (Chem. Abstr. 77:110348s, 1972).
Tilemans, E. and S. Dormal; 1952. Toxicite des produits phytopharm-
  ceutiques envers 1'homme et les animaux £ sang chaud.   Parasitica
  8:64-89.
Tokunaga, S.;  1968.  Metabolism of pentachlorophenol in fish and mam-
  mals.  I. Distribution of pentachlorophenol in fish.   Kagaku Keisatsu
  Kenkyusho Hokoku. 21:126-130.  (Chem. Abstr. 69:84467t, 1968).
Tsunoda, H.; 1965.  Pentachlorophenol (PCP) adsorption on soil.  I.
  Soil effect on PCP adsorption and  influence of PCP adsorption on the
  herbicidal efficiency of PCP.  Nippon Dojo-Hiryogaku Zasshi 36:187-
  190.  (Chem.  Abstr. 64:8860h, 1966).
                                   608
-------
Ukeles, R.; 1962.  Growth of pure cultures of marine phytoplankton in
  the presence of toxicants.  Appl. Microbiol. 10:532-537.
Vashakidze, V. I., R. N. Mandzhgaladze and V. S. Zhorzholiani; 1973.
  Toxicity of captan and its hygienic standardization in foods.  Gig.
  Sanit. 10:24-27. (Chem. Abstr. 80:34256e, 1974).
Vel-Muzquiz, R. and P. Kasper; 1974.  Effect of pentachlorophenol on
  the microbial flora of selected soils.  Microbiol. Espan. 26:21-30.
  (Chem. Abstr. 80:8l467j, 1974).
Verrett, M. J., M. K. Mutchler, W. F. Scott, E. F. Reynaldo and J. Mc-
  Laughlin; 1969.  Teratogenic effects of captan and related compounds
  in the developing chick embryo.  Ann. N.Y. Acad. Sci. 160:334-343.
Viel, G. and M. Chancogne; 1966.  Maneb decomposition.  The action of
  water and oxygen.  Phytiat.-Phytopharm. 15:31-39. (Chem. Abstr. 66:
  18265n, 1967).
Vinci, M.; 1953.  Action of methyl bromide in pregnancy.  Folia Med.
  36:899-907. (Chem.  Abstr. 48:6571d, 1954).
Vondruska, J. F., 0.  E. Fancher and J. C. Calandra; 1971.  Investiga-
  tion into the teratogenic potential of captan, folpet, and Difolatan
  in nonhuman primates.  Toxicol. Appl. Pharmacol. 18:619-624.
Vonk, J. W.; 1971.  Ethylenethiourea, a systemic decomposition product
  of nabam.  Meded. Fac. Landbouwwetensch., Rijksuniv. Gent. 36:109-
  112. (Chem. Abstr.  76:21724y, 1972).
Wainwright, M. and G. J. F. Pugh; 1974.  Effects of fungicides on cer-
  tain chemical and microbial properties of soils.  Soil Biol. Biochem.
  6:263-267.
Weinbach, E. C.; 1957.  Biochemical basis for the toxicity of penta-
  chlorophenol.  Proc. Natl. Acad. Sci. U.S. 43:393-397.
Wilson, H. A.; 1954.   The effect of certain pesticides on nitrifica-
  tion in the soil.  W. Va. Agr. Expt. Sta., Bull. 366T, 14 pp.; Soils
  and Fertilizers.  17:502. (Chem. Abstr. 51:12415a, 1957).
Winfree, J. P. and R. S. Cox; 1958.  Comparative effects of fumigation
  with chloropicrin and methyl bromide on mineralization of nitrogen
                                  609
-------
  in Everglades peat.  Plant Disease Reptr. 42:807-810.
Woolson, E. A., R. F. Thomas and P. D. J. Ensor; 1972.  Survey of
  polychlorodibenzo-p-dioxin content in selected pesticides.  J. Agr.
  Food Chem. 20:351-354.
Zhavoronkov, N. I., A. V. Akulov, S. D. Antsiferov, A. P. Verkhovskii
  and S. M. Evdokimov; 1973.  Effect of carbamates on hens.  Veteri-
  nariya 1973(8):114-116. (Chem. Abstr. 79:122422r, 1973).
                                  610
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                          SECTION VI SYNTHESIS
Figures 19, 20 and 21 summarize the data available for the 45 pesticides
reviewed in this report.  Persistence of both the original pesticide
and of its metabolites or contaminants were characterized as low, mod-
erate or high by the length of the bar on each graph, and the potential
transport was similarly ranked.  These were considered the primary cri-
teria for each pesticide's suitability for soil disposal.  Evaluation
of toxicity is included in the figures for completeness, as is the con-
clusion as to the feasibility of soil disposal, which is repeated from
Table 1.
The acute toxicity of a pesticide includes its effects on soil organisms,
aquatic organisms, birds and mammals, while chronic toxicity includes
reproductive effects and carcinogenesis.  The characterization of per-
sistence, transport and toxicity is qualitative by necessity.  Where the
available information is too incomplete even for qualitative conclusions,
unshaded bars were used.
Of forty-five pesticides, only ten are considered suitable for soil dis-
posal in the light of presently available data.  For several of these,
suitability is presumed despite very little information because of the
absence of unfavorable information.  Several organophosphate compounds
(methyl parathion, parathion, azinphosmethyl) are considered questiona-
bly soil disposable because recent data suggest they do not decompose
when massed in soil.  Therefore it must be stressed that the character-
ization of pesticides as suitable for soil disposal is optimistic, and
the number of such compounds will probably decrease as more data accu-
                                  611
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mulate.  In contrast, there is a small but carefully established body
of data on chemical and thermal disposal of certain pesticides.  Al-
though incineration of pesticides requires many precautions, it seems
more effective, and certainly more complete, than soil disposal.

We therefore conclude that incineration is a more promising mode of
pesticide disposal than is soil incorporation, and strongly recommend
its continued assessment.
                                 615
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                                  APPENDIX
      The data cited in this report are cited in metric units both in the tables
and in the text.  Where the data were originallly reported in other than metric
units, the following conversions were employed:


      soil treatments:       1 Ib/A = 1.12 kg/ha
      soil concentrations:  0.5 ppm = 1.0 kg/ha
      solutions:            1.0% = 10,000 ppm
                            1 mg/ml = 1,000 ppm
                                      616
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                                    TECHNICAL REPORT DATA
                            (Please read Instructions on the reverse before completing)
1. REPORT NO.
   EPA-600/9-77-022
                              2.
                                                            3. RECIPIENT'S ACCESSION-NO.
4. TITLE AND SUBTITLE
  The  Degradation of Selected Pesticides  in Soil:
  A Review of the Published Literature
                                      5. REPORT DATE
                                       August  1977 (Issuing Date)
                                      6. PERFORMING ORGANIZATION CODE
7. AUTHOR(S)
  James  R.  Sanborn
  B. Magnus Francis
                                                            8. PERFORMING ORGANIZATION REPORT NO.
   Robert L. Metcalf
9. PERFORMING ORGANIZATION NAME AND ADDRESS
  Illinois  Natural History  Survey
  University of Illinois
  Urbana,  Illinois  61801
                                      1O. PROGRAM ELEMENT NO.
                                      1DC618, SOS//4,  Task 04
                                      11. CONTRACT/GRANT NO.
                                        R-803591-01
12. SPONSORING AGENCY NAME AND ADDRESS
  Municipal Environmental  Research Laboratory—Cin.,  OH
  Office  of Research  & Development
  U.S.  Environmental  Protection Agency
  Cincinnati,  Ohio  45268
                                                             13. TYPE OF REPORT AND PERIOD COVERED
                                        2/23/75-5/1/76
                                      14. SPONSORING AGENCY CODE

                                        EPA/600/14
15. SUPPLEMENTARY NOTES
    Project Officer:
Richard  Games (513-684-7871)
16. ABSTRACT
   This  report contains  a  literature summary on the degradation of forty-five
   pesticides in soil.   The point of beginning of each literature review  is  the year
   of  issue of the patent  for the particular pesticide.  After compilation of  the
   literature data for each pesticide, conclusions were formulated regarding the
   suitability of soil disposal of these pesticides.  On the basis of the data
   collected in this report it was suggested that ten pesticides are suitable  for
   soil  disposal, twenty-one are not suitable for disposal,  and the data  for
   fourteen are insufficient to formulate  any conclusions  regarding their suitability
   for soil disposal.
17.
                                KEY WORDS AND DOCUMENT ANALYSIS
                  DESCRIPTORS
                        b.IDENTIFIERS/OPEN ENDED TERMS  C.  COS AT I Field/Group
   ^Pesticides
   Degradation
   Disposal
   Research
                                                        13  B
                                                        6 F
13. DISTRIBUTION STATEMENT

   RELEASE TO  PUBLIC
                        19. SECURITY CLASS {This Report)
                           TTnrl qggj
21. NO. OF PAGES
     633
                                               20 SECURITY CLASS (Thispage)

                                                 Unclassifiprl
                                                                          22. PRICE
EPA Form 2220-1 (9-73)
                                             617
                                                     , U S GOVERNMENT PRINTING OFFICE 1977-757-056/6507 Region No. 5-11
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