Note: Descriptions are shown in the official language in which they were submitted.
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This invention relates to a method o~ controlling
c~rtain arthropods, using the substituted thiophene,
2,3,5-triphenylthiophene as well as to a composition
useful in such method.
Arthropods which are controlled by the method o~
the invention include acarids, particularly plant-feeding
mite and mites and tickswhich af~lict man and animals,
as well as insect pestsJ
Plant-feeding mites produce enormous losses to
10 agricull;ural corps in a world plagued by constant shortages
o~ ~ood Crops such as al~al~a, apples, corn, cotton,
grapes, oranges, potatoes, sorghum, peanuts and many others
may be completely devastated by these tiny pests.
In additlon, various ~Ipecies have become so special-
15 lized in structure and habit t;hat they must subslst on the
bodies o~ man and animals. Few domesticated or wlld
animals are immune to their at;tack. Mites are expert at
torment~ng their host. There is probably no creature in
existence which can cause ~ore torMent ~or its size than
20 a "chigger" can by burrowing beneath the skln o~ man~
; Other species such as itch and mange mites eause
serious skin diseases in ~nimals such as dogs, cats,
rabbits~ horses, cattle and pigs.
Ticks and some species of mites suck the blood
o~ man ~nd animals. Besides the irritation involved~ a
multitude of anima~ diseases may be transmitted by this
method o~ food procurement Dread diseases such as Rocky
Mountaln spotted f`evcr, relapsln~ ~ever and tularemia are
tran~mltted by the bltes o~ ticks~ -
During the last thirty years, numerous chemicals
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have been utilized in protecting both man and man's food
and fiber against injury from mites and ticks, as well as
insects. There is a continuing need for novel, effective and
safe chemicals to accomplish this task. -
In accordance with the invention it has now been
found that the substituted thiophene 2,3,5-triphenylthiophene
is useful in the control of arthropods.
The invention is practiced by applying to a locus,
subject to a-ttack by certain arthropods, viz., acarids or
insects, an effective amount, viz., an acaricidal or
insecticidal amount, of the chemical 2,3,5-triphenylthiophene.
Frequently the locus is either plant life, for example such
crops as alfalfa, apples, corn, cotton, grapes, oranges,
potatoes, sorghum, peanuts, etc., or animal life, including man.
The chemical may be applied alone ~r with a carrier, which may
enhance the effectiveness of the active agent or facilitate
handling, to loci to be protected lagainst mites or the like,
for example as dusts when admixed with or absorbed on powdered
solid carriers, such as the various mineral silicates, e.g.,
mica, talc, pyrophillite and clays, or as liquids or spra~s
when in a liquid carrier, as in solution in a suitable solvent, ;
such as acetone, benzene or kerosene, or dispersed in a
suitable nonsolvent medium, for example, water. In protecting
plants (the term including plant parts) which are subject to
attack by these pests, the chemical employed in the present
invention is preferably applied as an aqueous emulsion contain-
ing a surface-active dispersing agent, which may be an
anionic, nonionic or cationic surface-active agent. Such
surface-active agents are well known and reference is made to
Canadian Patent No. 512,908 for detailed examples of the same.
The chemical may be mixed with such surface-active dispersing
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agents, with or without an organic solvent, as acaricidal
concentrates for subsequent addition of water to make aqueous
suspensions of the chemical of the desired concentration. The
chemical may be admixed with powdered solid carriers, such as
mineral silicates, together with a surface-active dispersing
agent so that a wettable powder may be obtained, which may be
applied directly to loci to be protected against mites or the
like, or which may be shaken up with water to form a suspension
of the chemical (and powdered solid carrier) in water for
application in that form. The chemical may be applied to loci
to be protected against mites or insects by the aerosol method.
Solutions for the aerosol treatment may be prepared by dissolving
the chemical directly in the aerosol carrier which is liquid
under pressure but which is a gas at ordinary temperature
(e.g., 20C.) and atmospheric pressure, or the aerosol solution
may be prepared by first dissolving the chemical in a less
volatile solvent and then admixing such solution with the highly
volatile liquid aerosol carrier. ~'he chemical may be used
admixad with carriers that are active of themselves, for example,
other insecticides, acaricides, fungicides, or bactericides.
Practical formulations ordinarily contain from 1 to
95~ active ingredient. Spray dilutions may range from a few
parts per million to undiluted concentrate applied by ultra low
volume techniques. The concentration of chemical per acre -~
would vary depending upon many factors, but normally range from
0.1 to 10 pounds.
In one aspect, the invention is directed to new
compositions useful in the control of certain arthropods,
comprising the desigr.ated substituted thiophene chemical, in
acaricidally or insecticidally effective amount, in combination
with a carrier therefor.
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The following examples will serve to illustrate
the practice ~f the invention in more detail.
Example 1 Mite Contact Test
Cotton, Gossypium hirsutum L. - variety Stoneville-
213, in the second primary leaf stage, grown in twelve ounce
cups under greenhouse conditions at 70-75F, was used in this
test. One plant (two primary leaves) in one pot was used for
each replicate; two replicates were used. A one-inch diameter
circle of tree tanglefoot, a sticky, non-toxic preparation,
was used to confine the mites to the upper leaf surfaces.
Approximately twenty-five adult two-spotted spider mites
(Tetranychus urticae) were transferred to each test plant ~4
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hours prior to treatment.
The test compounds were prepared for spraying at 1000
~ ppm (p~rts per million) concentration by dissolvin~ it
'. in a small amount of acetone and l~dding a ~uitable wett~ng
agent, Typlc~lly, o.6 grams of chemical were dissolved
(or suspended) in 10 ml o~ acetone, two drops of Triton~X100
(tradem~rk; octylphenoxy polyethoxy ethanol with 9-10 ~ole
percent of polye~hylene oxide) wetting agent were ~dded and
thls was ~uspended in 100 ml of water to make a 6000 ppm
suspenslon. An aliquot was then ~urther diluted with dis- :
tilled water to 1000 ppm concentration of chemical.
The infested plants were sprayed wlth the dls~ :
persion using a small spray atomi2er to thoroughly drench
the ~oliage. The plants were returned to the greenhouse
where they were held for six days. After this period the
plants were examined for adu~t li~e mites rem~ini~g on the
lea~es~ On an estimation basis and in comp~rlson with the
num~er o~ ing mites on the chec~ plants, the percent
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control W8S determined.
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In this mite contact test, 2,3,5-triphenylthiophene
produced 100% contact at 1000 ppm concentration.
In a similar test the known chemical 2,5-bis(phenyl-
thio)-thiophene (T. Fujisawa et al., Tetr. Letters, No. 49,
5071 [1968], which is outside the invention, displayed
miticidal activity, but was phytotoxic as evidenced by pucker-
ing of new growth. The known chemical 3,4-diphenylthiophene
(H. J. Backer and W. Stevens, Rec. trav. chim., 59, 423 [1940]),
which is outside the invention, showed no miticidal activity.
The known miticide 2-(~-t-butylphenoxy)cyclohexyl-2-propynyl
sulfite (Omite; trademark) was used at 80 ppm and 16 ppm for
mite control comparisons in a similar test; the LD95 for this
chemical ranges from 20 to 100 ppm depending on environmental
factors such as light intensity, temperature and humidity.
Exam~ 2 Mite One-Day Residual Te6t
Cotton, ~ S~æ~ hlrsutu~ L., ~ariety Stone-
~ille-213, in the ~econd primary llea~ stage, grown in
twel~e ounce cups under greenhouse condltions at 7O-75C,
wa~ used:in this t~st.
One plant ~two primary leaves) in one pot was
used for each replics.te; two replicates were used for
e~ch concentra~ion of chemical te~ted.
The test compound was prepared by dissolving 50
mgs of chemical in one ~1 of acetone, adding one drop o~ .:
Emul~or 719~ a commercial sur~ ce-~ctive disper~lng agent
(trademark; polyoxyethylated vegetable oll) and suspended
in 5O ml o:E water ~or ~ t~oncentrat~on of 1000 ppm (parts
per milllon). Aliquot~ were ~urther diluted with dis-
tilled water to the concentration tested.
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The plants ~ere sprayed with the di~persions o~
the chemical, using a small ~pray atomiæer to th~roughly
dr~nch the f~llage.
One day following treatment a circle of tree
tangle-foot was placed on the upper surfaces of the
treated leaves and adult mites were transferred into
this con~inement. Counts of these mites were made im-
mediately following transfer and again six days later.
Abbott~s formula was used to compensa~e for check
mortallty. The ad~usted percent control w~s obtained
by the following expression~ wherein A is the ad~usted
control~ C is the ~ liYe mltes on check plants and T
ls the ~ live mites on treated plants:
C-T _ _ X 100
Dsta from the ~ite one-day residual te~t ~re shcwn
in Table I.
_ble I
Mite One Day Residual Test
of 2,3,5-Triphenylthi~phene
~ Control
1000 500 100
PPM PPM PPM
100 100 100
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Example 3
This example illustrates a citrus rust mite test.
Grapefruit trees, of the variety Thompson Pink, were treated
in this test conducted at Sanford, Florida. The trees were
naturally infested with a population of the citrus rust mite,
Phyllocoptruta oleivora, which is a pest that feeds on both
foliage and fruit of citrus trees. Four replicate trees were
treated with each chemical rate. Sprays were applied at
lO0 lbs. pressure with a spray gun which was used to drench
the foliage. In the counting procedure, twenty-five leaves
were sampled on each tree, lO0 leaves per treatment. A one-
square-inch area of each leaf was examined with a hand lens.
A density index number was recorded for each leaf examined as
follows - O = no mites, l-l-2 mites, 2=3-6 mites, 3=7 or more
mites. These index numbers were then totalled and divided by
the number of leaves to provide an average density rating.
The percent reduction of citrus rust mite density
over the untreated checks was then calculated by adaptation
of Abbott's formula:
Density Rating
Reduction = Check - Treated X lO0
Density rating of check
Counts were made at intervals after treatment, as
indicated in Tables II and III.
The results on Table II indicate that the compounds
employed in this invention, namely 2,3,5-triphenylthiophene/
compares most favorably with a widely used commercial product
where the long range control of citrus rust mites ls concerned.
Table III provides additional evidence that the compound
employed in this invention is most suitable for the control of
citrus rust mites. ~ `
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. TABLE III
Percent Reduction of Citrus Rust Mite Density Using
:~ 2,3,5-Triphenylthiophene Over the Untreated Check
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Rate
PPM 10 Days Post-Treatment
200 65
*10 leaves counted/rep. Each rep. equalled ~ .
~ a 12-inch branch tip isolated with Tanglefoot.
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The invention is remarkable for its ability to control
the citrus rust mite on oranges, grapefruit and similar crops.
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