FAO/PL:1969/M/17/1
WHO/FOOD ADD./70.38
1969 EVALUATIONS OF SOME PESTICIDE RESIDUES IN FOOD
THE MONOGRAPHS
Issued jointly by FAO and WHO
The content of this document is the result of the deliberations of the
Joint Meeting of the FAO Working Party of Experts and the WHO Expert
Group on Pesticide Residues, which met in Rome, 8 - 15 December 1969.
FOOD AND AGRICULTURE ORGANIZATION OF THE UNITED NATIONS
WORLD HEALTH ORGANIZATION
Rome, 1970
BINAPACRYL
IDENTITY
Chemical name
2,4-dinitro-6-s-butylphenyl 3-methylcrotonate
Synonyms
2-sec-butyl-4,6-dinitrophenyl 3-dimethylacrylate, Acricid(R),
Morocide(R), Endosan(R), Ambox(R)
Structural formula
Other relevant chemical properties
The technical material is claimed to contain 96 percent binapacryl;
the composition of the remaining 4 percent has not been revealed. The
vapour pressure of the pure product is 1 × 10-4 Torr at 60°C. The
solubility in water is low, moderate (11 percent) in ethanol and
kerosene, but exceeding 50 percent in heavy aromatic naphtha,
isophorone, xylene and acetone.
Binapacryl is stable under normal conditions but is decomposed slowly
by U.V. radiation. It is readily hydrolyzed by strong acids or dilute
alkalis; a small degree of hydrolysis will occur in water after
prolonged contact.
Formulated products include wettable powders containing 50 percent
a.i. (formerly 25 percent a.i.), an emulsifiable concentrate (40
percent a.i.), a 'Col' suspension (50 percent w/v a.i.), and dusts (3
or 4 percent a.i.).
EVALUATION FOR ACCEPTABLE DAILY INTAKE
BIOCHEMICAL ASPECTS
Absorption, distribution and excretion
When male and female dogs were fed daily oral doses of 1 or 10 mg/kg
body-weight of binapacryl, the faeces were found to contain mainly the
unchanged compound; but only small amounts of binapacryl itself were
found in the urine, blood and organ tissues. Three dinitro-metabolites
were found and the metabolic pathway shown in Figure 1 was proposed.
There were no amine or conjugated metabolites found in the blood and
urine in dogs. About 70 percent of the phenol, dinoseb (II), formed in
the blood, was converted to the alcohol (III). This alcohol was
detected in both blood and urine, whereas the acid (IV), formed from
its oxidation, was only found in the urine (Chin and Stanovich, 1964).
A similar indication of low absorption of unchanged binapacryl, as
well as rapid biotransformation to dinoseb, before or after
absorption, was found in guinea-pigs. In these studies, fasted
guinea-pigs were given a single dose of either 400 mg/kg body-weight
of binapacryl or 40 mg/kg of dinoseb by stomach tube. No binapacryl
could be detected in the blood prior to death, but the concentration
of dinoseb in the blood was within the same range in both groups,
indicating that the toxic effect of binapacryl is due to its
hydrolytic product, dinoseb (Bough et al., 1965).
Rabbits given oral doses of 60 mg/kg body weight of binapacryl or 20
mg/kg of dinoseb excreted five metabolites in the urine, one of which
was 2-(2-butyl-)-4-nitro-6-aminophenol, present both in a free and in
a glucuronide-conjugated form. In the urine of rats only traces of the
amine and none of the conjugated form was found. In both species,
metabolites resulting from side-chain oxidation, e.g.
3-(2-hydroxy-3,5-dinitrophenyl)-butyric acid, were found (Ernst and
Bär, 1964).
Quantitative studies of the urinary excretion in rats and rabbits
after a single administration of binapacryl was found to be 7 - 17
percent of the applied dose within 48 hours. Even during the tenth day
0.12 percent of the dose administered was detected in urine from rats
(Ernst and Bär, 1964).
TOXICOLOGICAL STUDIES
Special studies on cataract formation
Chicken
Groups of 15 chickens were fed binapacryl, dinocap or
2,4-dinitrophenol in the diet for 17 - 28 days. The incidence of lens
opacities was investigated by gross autopsy on dead or killed birds.
At dietary levels of 900 and 1800 ppm of binapacryl, of 1000 and 2000
ppm of dinocap and 500, 1000 and 2000 ppm of dinitrophenol no
opacities were found. At dose levels of 3500 ppm of binapacryl, 4000
ppm of dinocap and 3000 ppm of dinitrophenol and at higher levels
there was a distinct incidence of cataracts (Cervenka and Kay, 1963).
Special studies on reproduction
Rat
Groups of rats (8 males and 16 females) were fed 0, 1, and 50 ppm of
binapacryl for three generations. The F0, F1b and F2b generations
were used as parents. The reproductive performance as measured by the
indices of mating, pregnancy, fertility, parturition and lactation,
was not influenced by the feeding with binapacryl. Neither were the
different parameters of the progeny e.g. litter size, number of
stillbirths, viability, survival and weight of weanlings. No special
teratological studies were carried out, but upon weaning of the F3b
litters, gross and histological examination of several of the animals
from all groups did not reveal any changes attributable to binapacryl
(Kennedy and Calandra, 1965a, 1965b, 1965c).
Special studies on the metabolite, dinoseb
[2-(2-butyl)-4,6-dinitrophenol]
Comparative toxicity of dinoseb and binapacryl
In acute toxicity and blood level studies on binapacryl and dinoseb in
a variety of small animals covering a wide range of doses, binapacryl
was found to be considerably less toxic than dinoseb whether the
compounds were administered orally (mouse, rat, guinea-pig and
chicken) or percutaneously (guinea-pig and rabbit) (Bough et al.,
1965).
The table shown under the heading "Acute toxicity" compares the LD50
values for binapacryl and dinoseb in several species.
Short-term studies
Groups of male rats, comprising 30, 20, 20, 20 and 10 in number, were
fed 0, 50, 100, 200 and 500 ppm, respectively, of dinoseb in their
diet for up to six months. Of the 10 rate fed 500 ppm there was rapid
weight loss and 4 died within two weeks. The survivors were sacrificed
after three weeks and showed marked emaciation and, upon histological
examination, slight degenerative changes in the kidney and cloudy
swellings in the liver cells were found. In the groups fed 200 ppm or
less, growth, mortality, haematology, bone-marrow count and blood-urea
nitrogen determination at the end of the six month period, as well as
average organ weights and histopathology were comparable with the
controls, except for a slight decrease in growth rate and increase in
liver weight in the group fed 200 ppm (Spencer et al., 1948).
Acute toxicity
Most of the studies on the acute toxicity of binapacryl are of a
rather preliminary nature, but indicate the range of tissues within
which the LD50 might be found. The following table also compares the
values with those found for the metabolite, dinoseb:
LD50
mg/kg body-weight
Animal Route Binapacryl Dinoseb Reference
Mouse (M) oral 1600-3200 20-40 Bough et al., 1965
Rat (M) oral 150-225 25-40 Bough et al., 1965
Rat oral 150-225 50 Edson et al., 1966
Rat (mixed) oral 220-350 Hoechst, 1964
Rat (mixed) oral 38 Spencer et al., 1948
Rat dermal 80-200 Edson et al., 1966
Guinea-pig (F) oral 200-400 20-40 Bough et al., 1965
Guinea-pig (mixed) dermal 150-200 Spencer et al., 1948
Rabbit (mixed) oral 640 Hoechst, 1964
Rabbit dermal 1350 Edson et al., 1966
Dog oral 450-640 Hoechst, 1964
Chicken (M) oral 800 40-800 Bough et al., 1965
Short-term studies
Dog
Groups of dogs (three males and three females) were given 0, 0.25,
1.25, 2.5, 5, and 25 mg/kg body-weight of binapacryl orally in
gelatine capsules daily for two years. In the groups given 5 mg/kg and
below mortality, food, consumption, body-weight, behaviour,
haematology, blood biochemistry, urinalysis, liver function tests,
organ-weight, organ to body-weight ratios, gross and microscopic
pathology were comparable to the controls. The groups given 1.25, 2.5,
and 5 mg/kg displayed a transient paresis of the hindquarters lasting
5-10 hours after dosing. In the group given 25 mg/kg, depression and
continuous paresis of the hindquarters wore observed, and all the dogs
in this group died within six months (Baran at al., 1966).
Rat
Groups of rats (10 males and 10 females) were fed 0, 25, 50, 100, and
200 ppm of binapacryl in their diet for 90 days. Mortality, general
condition, haematology, urinalysis, average organ-weight, gross and
microscopic pathology were comparable in the experimental and the
control groups. A slight decrease in weight gain occurred in the
groups fed 100 and 200 ppm. The experiments were part of a two-year
study (Hoechst, 1962).
In a 64-week study, from which no detailed information is available,
groups of rats (30 males and 30 females) were fed 0, 25, 100, and 500
ppm of binapacryl in the diet. Of the parameters tested only a
depression of body-weight was noted in the 100 and 500 ppm groups
(Industrial Bio-Test Laboratories Inc., 1964).
Long-term studies
Rat
Groups of rats (30 males and 30 females) were fed 0, 25, 50, 100, and
200 ppm of binapacryl in the diet for two years. After 90 days, 10
males and 10 females were withdrawn from the experiment and evaluated
separately (see "Short-term studies"). After one year of feeding
approximately half of the remaining rats in the groups were subjected
to interim sacrifice. Although a number of rats succumbed to
intercurrent disease (pneumonia) during the two-year study, no effect
on morbidity or mortality due to binapacryl was found. Food
consumption, body-weights, haematology, urinalysis, average
organ-weights, gross and microscopic pathology (including tumour
incidence) were comparable in the experimental and control groups
(Hoechst, 1962).
COMMENT
Although the metabolism of binapacryl has been studied in several
species, more studies on the absorption and excretion of the compound
would be desirable. The short and long-term feeding study and the
three-generation reproduction study in the rat as well as the two-year
feeding study in the dogs are considered adequate. The observation of
cataracts in chickens fed high-dose levels is of come concern. The
two-year dog study is used as a basis for establishing an acceptable
daily intake.
TOXICOLOGICAL EVALUATION
Level causing no toxicological effect
Rat: 200 ppm in the diets equivalent to 10 mg/kg body-weight/day
Dog: 0.25 mg/kg body-weight/day
ESTIMATE OF ACCEPTABLE DAILY INTAKE FOR MAN
0-0.0025 mg/kg body-weight
RESIDUES IN FOOD AND THEIR EVALUATION
USE PATTERN
Pre-harvest treatments
Binapacryl is an acaricide of value for control of tetranychid mites
on certain fruits, mainly apple, and vegetables. It is also used to
control powdery mildew on apple. There is no evidence of systemic
action.
In England, in 1967, about 5,000 hectares of apples, mainly dessert,
were sprayed at the recommended rate, 4 lb of the 25 percent W.P.
then available per acre (1.16 kg a.i. per he), on average six or seven
times at two-week intervals. In the U.S.A., binapacryl is registered
for use on top fruit at 4 oz a.i. per 100 gal. (25 g per 100 litres),
using not more than 4 lb of the 50 percent W.P. per acre (2.3 kg a.i.
per ha). In West Germany, the recommended two-week rate is 0.1 percent
of the 50 percent W.P. at 2,000 litres per ha (1 kg a.i. per ha), the
current recommendation In the U.K. being 1.16 kg a.i. per ha.
Post-harvest treatments
A 4 percent dust is registered in the U.S.A. for use at 50 lb per acre
(2.3 kg a.i. per ha) on cropping trees.
RESIDUES RESULTING FROM SUPERVISED TRIALS
Residues at intervals up to harvest have been reported (Buxton, 1962,
1963; Emmel, 1960; Maier-Bode, 1967, unpublished; Maier-Bode, 1968;
Stanovich, 1963; Versier, 1965). They are summarized in the following
table:
Rate Interval Residues*
Crop Year a.i. (days) (ppm)
Apples 1.25 kg/ha 24 0.1-0.2
0.05% 0 1.4
7 0.15
2.5 kg/ha 0 1.4
7 0.35
14 0.25
2.0 kg/ha 0 0.3
7 0.1
14 0.02
(continued)
Rate Interval Residues*
Crop Year a.i. (days) (ppm)
Apples 2.0 kg/ha 0 1.1
(cont'd) 7 0.6
14 <0.02
1.5 kg/ha 14 0.5-0.64 (<0.02)
1.5 kg/ha 0 1.62 (<0.02)
7 1.50-1.54
14 1.14-1.31
1.5 kg/ha 0 2.0-2.2 (0.02)
7 0.91-1.06
14 0.80-0.87
22 0.37-0.45
2.2 kg/ha 0 1.1-2.0 (0.02)
5 0.5-1.13
11 0.11-0.53
14 0.27-0.32
0.125% 0 1.20 (0.10)
7 0.38 (0.05)
15 0.10 (0.03)
0.03% ) 0 1.00-1.08 (0.04)
1.7 kg/ha ) 7 0.56-0.59 (0.02)
14 0.51-0.68 (0.02)
21 0.26-0.45 (0.02)
0.06% 0 1.50 (0.02)
7 0.82-0.97
16 0.29-0.48
21 0.23-0.24
Pears 0.03% 0 3.0 (0.02)
5 1.87-2.3
11 0.98-1.09
19 0.34-0.35
0.05% 6 3.3-3.7 (0.05)
14 0.8-1.1
27 0.15
0.03% 0 0.5 (<0.02)
15 0.36
29 0.06
0.03% 0 3.4 (0.03)
7 1.39-1.44 (0.04)
14 0.58-0.61 (0.03)
21 0.14 (<0.02)
0.09% 0 6.9 (0.06)
Pears (continued)
Rate Interval Residues*
Crop Year a.i. (days) (ppm)
Pears 7 3.3-4.4 (0.06-0.1)
(continued) 14 2.8 (0.06)
21 1.12-1.32 (0.03)
Peaches 0.03% 0 8.3 (0.05)
7 3.7-4.1 (0.07-0.08)
14 3.2-3.3 (0.07-0.08)
21 1.6-1.7 (0.06)
28 0.94-1.12 (0.02)
0.09% 0 14.1 (0.13)
7 7.0-9.3 (0.19)
14 6.4-6.7 (0.17)
21 3.4-4.0 (0.15)
28 2.3-2.4 (0.07)
0.03% 0 8.7-12.0 (0.03)
15 1.25-2.2 (0.02)
30 0.38-0.40 (<0.02)
45 0.15-0.35
0.03% 58 (fresh) 0.03
72 (dried) <0.1
0.09% 58 (fresh) 0.1-0.18
72 (dried) 0.1
0.03% 0 4.5-5.9 (0.13-0.17)
7 2.5-3.4 (0.12-0.18)
14 1.26-1.45 (0.06)
22 0.61-0.64 (0.03)
30 0.36-0.40 (0.02)
Plum 0.05% 0 0.14 (<0.02)
(including 7
prune) 14 0.10-0.13
21 0.07
28 0.03-0.09
0.05% 0 0.22-0.25
7 0.38-0.41
14 ) 0.12-0.13
21 )
28 0.06
0.03% 1 0.53-0.67 (<0.02)
13 0.16-0.28
27 0.11-0.15
0.03% 0 0.91-1.06 (0.02)
5 0.45-0.58
12 0.29-0.71
20 0.18-0.22
(continued)
Rate Interval Residues*
Crop Year a.i. (days) (ppm)
Plum 0.03% 24 (fresh) 0.18-0.21
(cont'd) (dry) 0.02
39 (fresh) 0.06-0.08
(dry) <0.02
Grapes-Thompson 1963 2 kg/ha 0 5.2-5.3 (0.04)
Seedless (dust) 5 2.4-2.8 (0.06)
12 0.9-1.5 (0.05)
29 0.25-0.5 (0.02)
Grapes-Thompson 1963 2.3 kg/ha 0 9.0-9.4 (0.06-0.08)
Seedless (dust) 14 1.6-2.8 (0.05-0.08)
28 0.8-1.3 (0.02-0.06)
43 0.24-0.27 (<0.02)
Grapes-Thompson 1963 2.2 31 (fresh) 0.51-0.54
Seedless 49 (dry) 0.16-0.21
1.7 29 (fresh) 0.35-0.42
63 (dry) 0.07
2.2 29 (fresh) 1.5-4.3
63 (dry) 0.32-0.52
2.2 50 (fresh) 0.39-0.40
84 (dry) 0.11-0.18
Grapes-Thompson 1963 2.2 0 3.0 (0.02)
Seedless 9 1.87-3.1 (0.03)
21 1.33-1.96 (0.04)
28 0.34-0.46 (<0.02)
42 0.15-0.54
Grapes-Thompson 1963 2.2 0 6.1-6.2 (0.04)
Seedless 7 3.5-3.7 (0.04)
15 1.6-2.2 (0.04)
21 0.7-1.3 (0.02)
31 0.51-0.54 (<0.02)
Grapes-Thompson 1963 1.7 7 0.65-1.09 (<0.02)
Seedless 21 0.87
29 0.35-0.52
2.2 7 5.9-6.2 (0.03)
21 2.1-4.6 (0.05)
29 1.31-4.3 (0.04)
Grapes-Thompson 1963 2.0 0 9.4-13.6 (0.05-0.09)
Seedless (dust) 7 2.6-3.5 (0.03-0.05)
16 1.3-2.0 (0.04)
21 0.3-0.6 (<0.02)
28 0.1-0.17
(continued)
Rate Interval Residues*
Crop Year a.i. (days) (ppm)
Grapes Thompson 1962 0.7 kg/ha 0 1.01 (0.02)
Seedless 13 0.16 (<0.02)
31 0.03 (<0.02)
45 <0.02
Grapes-Thompson 1962 2.0 kg/ha 0 0.60 (0.02)
Seedless (dust) 14 0.05 (<0.02)
28 <0.02
Grapes-Thompson 1962 2.0 kg/ha 7 0.36-1.22 (0.03)
Seedless (dust) 14 0.05-0.16 (<0.02)
28 0.03-0.04 (<0.02)
49 <0.02
Grapes-Thompson 1962 0.7 kg/ha 57 <0.02
Seedless (3 sites) fresh or dried
Grapes-Thompson 1962 0.7 kg/ha 45 <0.02
Seedless (2 sites) 60 <0.02
fresh or dried
Muscat 1962 0.7 kg/ha 57 (fresh) <0.02
83 (dried) <0.02
Cucumber 1963 0.06% 16 0.5
Cucumber 1963 0.15% 7 0.5
(greenhouse) 12 0.3
15 nil
0.2% 7 1.0
12 0.2
15 0.5
Nectarine 1962 1.8 kg/ha 0 0.61 (<0.02)
7 0.24 (<0.02)
15 0.09 (<0.02)
29 0.04 (<0.02)
44 <0.02
Nectarine 1962 1.8 29 <0.02
Nectarine 1962 2.2 0 0.71 (<0.02)
7 0.52-0.54
15 0.24-0.27
21 0.15-0.17
28 0.11-0.12
43 0.06
(continued)
Rate Interval Residues*
Crop Year a.i. (days) (ppm)
Nectarine 1963 1.7 0 0.87-0.90 (<0.02)
13 0.26-0.29
28 0.08-0.11
42 0.06-0.08
2.2 0 1.03-1.19 (<0.02)
13 0.44-0.49
28 0.22-0.23
42 0.10-0.11
* Data in parentheses are for free dinoseb
FATE OF RESIDUES
In plants
The rate of loss of binapacryl from leaf surfaces is fast. In the
spraying experiment on plum trees using the 40 percent E.C., initial
leaf deposits averaged 95 ppm; these fall to 5 ppm after two weeks and
to less than 0.2 ppm after four weeks (Farbwerke-Hoechst AG.). The
rate of disappearance from fruit surfaces, reported from many
supervised trials is lower; it is usually logarithmic with time.
The presence of small amounts of unesterified dinoseb, or fairly rapid
hydrolysis of small amounts of binapacryl, may account for the
bleaching of foliage on certain pear varieties (Kirby and Bennett,
1967) and on several apple varieties (Slade, 1966; Kirby,
unpublished). Residue analyses from the U.S.A. report the presence of
traces of dinoseb on various fruits sprayed with binapacryl, but these
are rarely much above the limit of detection (0.03 ppm); Maier-Bode
(1968) could not find any free dinoseb. Considerable foliar scorch
occurred on rooted shoots of apple kept at 100 percent R.H. after
dipping in 100 to 200 ppm suspensions of binapacryl as the 25 Percent
W.P.; plants dipped and maintained at normal glasshouse humidities
were unaffected (Kirby et al., 1964). French bean (Phaseolus
vulgaris) leaves were treated with binapacryl at 1.5 mg per 30 cm2
and maintained at 22°; if the R.H. was 100 percent, no dinoseb was
detected at any time, but at 40 percent traces of dinoseb (0.04 1.19
from 8 to 10 leaves) were found during the course of a week
(Farbwerke-Hoechst AG.).
In soils
Evidence has been obtained that degradation of binapacryl that occurs
in muck soil in due to microbial action (Chin and Stanovich, 1965).
Evidence of residues in food in commerce or at consumption
No report of binapacryl residues in foodstuffs being sold or prepared
for consumption has been seen so far.
METHODS OF RESIDUE ANALYSIS
Residue of binapacryl can be determined by several colorimetric
procedures applicable to dinitrophenol compounds, provided a
hydrolysis stage is included in the sample preparation, The methods of
Schechter and Haller (1944), Kilgore and Cheng (1963), Potter (1963)
and Abbott and Thomson (1964) are suitable for the resultant
dinitrobutylphenol (dinoseb). Buxton and Mohr (1968) recommend a
procedure based on the colour formed when binapacryl, or its principal
decomposition product dinoseb, is treated with pyridine, optical
densities being read at 435 nm. A sensitivity of about 0.03 ppm of
binapacryl is achieved by this method which has been used on stone and
pome fruits, strawberries, grapes and cucurbits; it is not
sufficiently sensitive for hops or cottonseed. Residues of
dinitrophenols arising from other sources would also be included in
the figures obtained.
An electron-capture gas chromatographic method is also mentioned by
Buxton and Mohr (1968) but no details are given. The separatory
systems used by Clifford and Watkins (1968) for dinitroalkylphenols
and by Boggs (1966) and Yip and Howard (1968) for their methyl ethers
should be applicable to the determination of hydrolysed binapacryl
residues. The development and evaluation of such methods for
regulatory purposes is desirable.
NATIONAL TOLERANCES
Country Crop Tolerance (ppm)
Australia Pome and stone fruits 2.0*
Belgium Fruits and vegetables 0.3
Canada do. 1.5
France do. 0.3
Germany (Fed. Rep.) do. 0.3
Italy do. 0.3
Luxembourg do. 0.3
(cont'd)
Country Crop Tolerance (ppm)
Netherlands do. 0.3
United States of America do. 0.22*
* These levels are provisional
APPRAISAL
Binapacryl is a non-ovicidal acaricide and a fungicide of economic
value against powdery mildews only. Its use on apple is widespread in
Europe and Australasia, but very limited so far in North America. Use
on other fruits and other crops appears to be slight. Mitotoxicity on
apple and pear under some circumstances is a drawback. No use on
animals is known. The technical product is claimed to contain 96
percent binapacryl; nature of impurities not reported. Wettable
powders are now being supplemented by stable aqueous suspensions.
Residues from recommended applications normally fall to less than 1
ppm on pome, stone and soft fruits within one week after the final
application, this being the minimum pre-harvest interval. The
persistence (half-life) of the technical a.i. is reported to be short.
Non-toxicity of binapacryl will depend on the stability of the ester
linkage; this stability seems to be great in the mammalian food tract.
Traces of dinoseb are sometimes found on fruit sprayed with
binapacryl, but these are rarely above the limit of detection (0.03
ppm). There is very little dermal absorption. Metabolites found
include the monoamino reduction product and an acid formed by
oxidation of the s-butyl side-chain.
RECOMMENDATIONS FOR TOLERANCES, TEMPORARY TOLERANCES OR PRACTICAL
RESIDUE LIMITS
TOLERANCES
Apples, pears, grapes 0.5 ppm
Plums 0.3 ppm
Nectarines 0.2 ppm
Peaches, cherries 1 ppm
FURTHER WORK OR INFORMATION
DESIRABLE
1. Further work on the absorption and the excretion rates in rats or
other species.
2. Reproduction and teratogenicity studies in a non-rodent mammalian
species.
3. More studies on possible cataract formation in animals.
4. Further information on the unidentified fraction of the technical
product.
5. Residue data from countries other than the U.S.A.
6. The development and evaluation of a GLC method suitable for
regulatory purposes.
REFERENCES
Abbott, D.C. and Thomson, J. (1964) Wedge-layer clean-up of dinoseb
extracts. Analyst, 89:613-5
Baran, J., Fancher, O.E. and Calandra, J.C. (1966) Two-year oral
toxicity of NIA-9044 (Morocide) - beagle dogs. Unpub. Rept. from
Industrial Bio-test Laboratories Inc., to Niagara Chemical Division,
FMC Corporation, submitted by Farbwerke Hoechst AG.
Boggs, H. (1966) Gas chromatography of dinitro herbicides. J. Assoc.
Offic. Anal. Chem. 49:772-3
Bough, R.G., Cliffe, E.E. and Lessel, E. (1965) Comparative toxicity
and blood level studies on binapacryl and DNBP. Toxicol. appl.
Pharmacol., 7:353-60
Buxton, R.W. (1962) R-522. Morocide (Residues on fresh and dried
grapes, peaches and pears). Niagara Chem. Div., FMC Corp., New York.
Unpub. Rept.
Buxton, R.W. (1963) R-674. Morocide (Residues on peaches). Niagara
Chem. Div., FMC Corp., New York. Unpub. Rept.
Buxton, R.W. and Mohr, T.A. (1968) in, Analytical Methods for
Pesticides, Plant Growth Regulators and Food Additives, ed. by G.
Zweig, Vol.V, pp.239-42
Cervenka, H. and Kay, J.F. (1963) Cataractogenic studies. Unpub. Rept.
from Industrial Bio-test Laboratories Inc., to Niagara Chemical
Division, MC Corporation, submitted by Farbwerke Hoechst AG.
Chin, W.T. and Stanovich, R.P. (1964) Metabolism of Morocide by dogs.
Unpub. Rept. M-1431, from the Research and Development Department,
Niagara Chemical Division, FMC Corporation, submitted by Farbwerke
Hoechst AG.
Chin, W.T. and Stanovich, R.P. (1965) M-1604. Biological influence on
the hydrolysis of Morocide in muck soil. Niagara Chem. Div., FMC
Corporation, New York. Unpub. Rept.
Clifford, D.R. and Watkins, D.A.M. (1968) The gas chromatography of
dinitroalkyl phenols. J. Gas Chromatog., 6:191-2
Edson, E.F., Sanderson, D.M.. and Noakes, D.N. (1966) Acute toxicity
data for pesticides (1966). World Revue of Pest Control, 5:143-51
Emmel, L. (1960) Uber ein neuartiges Akarazid auf Basis van
Dinitroalkylphenylacrylat. Meded. LandbHogesch. OpzoekStns, Gent,
1370-6
Ernst, W. and Bär, F. (1964) Die Unwandlung des
2,4-Dinitro-6-sec-butyl-phenols und seiner Ester im tierischen
Organismus. Arzneimittel.-Forsch., 14:81-4
Farbwerke-Hoechst AG. (1969) Binapacryl. Unpub. Rept.
Hoechst. (1962) Chronische Toxizitätsstudien mit Acricid = Hoechst
2784 über 2 Jahre an Ratten. Unpub. Rept. submitted by Farbwerke
Hoechst AG.
Hoechst. (1964) Prüfung van Acricid-Wirkstoff (Binapacryl) auf akute
orale Toxizität an Ratten, Kaninchen und Hunden. Unpub. Rept.
submitted by Farbwerke Hoechst AG.
Industrial Bio-test Laboratories Inc. (1964) Status summary. Chronic
oral toxicity of Nia 9044 (Morocide). Albino rats. Unpub. Rept. to
Niagara Division, FMC Corporation, submitted by Farbwerke Hoechst AG.
Kennedy G. and Calandra, J.C. (1965a) Three generation reproduction
study in albino rats on Morocide: first generation. Unpub. Rept. from
Industrial Bio-test Laboratories Inc., to Niagara Chemical Division,
FMC Corporation, submitted by Farbwerke Hoechst AG.
Kennedy, G. and Calandra J.C. (1965b) Three generation reproduction
study on Morocide - Albino rats: Second generation. Unpub. Rept. from
Industrial Bio-test Laboratories Inc. to Niagara Chemical Division, MC
Corporation, submitted by Farbwerke Hoechst AG.
Kennedy, G. and Calandra, J.C. (1965c) Three generation reproduction
study on Morocide - Albino rats: Final report. Unpub. Rept. from
Industrial Bio-test Laboratories Inc., to Niagara Chemical Division,
FMC Corporation, submitted by Farbwerke Hoechst AG.
Kilgore, W.W. and Cheng, K.W. (1963) Extraction and determination of
Karathane residues in fruits. J. Agr. Food Chem., 11:477-9
Kirby, A.H.M., Frick, E.L., Hunter, L.D., and Tew, R.P. (1964)
Relative fungitoxicities of some dinitroalkylphenols. Tetrahedron, 20:
Suppl. 1, 483:508
Kirby, A.H.M. and Bennett, M. (1967) Phytotoxicity to pear of some
fungicides controlling powdery mildews. Rep. E. Malling Res. Stn. for
1966, 181-5
Maier-Bode, H. (1968) Uber die Persistenz des Akarazids Binapacryl. Z.
PflKrnankh. PflPath. PflSchutz, 75:321-7
Potter, J.A. (1963) The determination of dinoseb in potatoes. Analyst,
88:651-3
Schechter, M.S. and Haller, H.D. (1944) Colorimetric determination of
2,4-dinitroanisole. Ind. Eng. Chem. Anal. Ed., 16:325-6
Slade, D.A. (1966) New fungicides for apple disease control. Orchard.
N.Z., 39:393-7
Spencer, H.C., Rowe, V.K., Adams, E.M. and Irish, D.D. (1948)
Toxicological studies on laboratory animals of certain
alkyldinitrophenols used in agriculture. J. Industr. Hyg. Toxicol.
30:10-25
Stanovick, R.P. (1963) M-1204. Determination of Morocide and
dinitrobutylphenol residues on apples, pears and cucumbers. Niagara
Chem. Div., FMC Corporation, New York. Unpub. Rept.
Versier, R. (1965) Evolution at importance des résidus de fongicides
utilisés en arboriculture fruitière. Congr. Internat.
d'Antiparasitaires, Naples
Yip, G. and Howard, S.F. (1968) Extraction and clean-up procedure for
the gas chromatographic determination of four dinitrophenol
pesticides. J. Assoc. Offic. Anal. Chem. 51:24-28
See Also:
Toxicological Abbreviations
Binapacryl (ICSC)
Binapacryl (WHO Pesticide Residues Series 4)
Binapacryl (Pesticide residues in food: 1984 evaluations)
Binapacryl (Pesticide residues in food: 1985 evaluations Part II Toxicology)